Family vacation retreat w/ In-ground Pool with private Chesapeake Bay access!
4.8
Outstanding(36 Reviews)House in Chesapeake Bay, NC
12 guests · 6 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Includes essentialsGarden, Pool, Kitchen or Kitchenette and more
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Located for easy access to our private beach, Kiptopeke State Park, Cape Charles, and Virginia Beach. This is the ideal family get-away for 4-5 couples. Completely modern with loads of privacy, it can accommodate up to 12 guests and has two separate living areas. When you're not splashing in the pool, you can take a 1-minute drive to stroll the nicest beach on the Eastern Shore. It is about 6 minutes to Kiptopeke State Park with its great beach, nature trails, fishing pier, and boat ramps, and 12 minutes to the Town of Cape Charles with its restaurants, stores, beaches, parades, marinas, golf courses, and more!
It's a 45-minute drive to the Virginia Beach oceanfront and about an hour and a half to Chincoteague where you can tour the islands and see the wild ponies and Osprey nests. Williamsburg is a 1 1/2 hour drive; a perfect day trip. Experience a slower pace of life with access to all the fun you want.
Note: The pool is open for Memorial Day. Please let me know if you'd like it opened earlier in the season.
Please note: Loud music and parties are not tolerated. This is a very quiet, peaceful community, and excessive noise is not tolerated. Thank you for your understanding and acceptance of this condition.
It's a 45-minute drive to the Virginia Beach oceanfront and about an hour and a half to Chincoteague where you can tour the islands and see the wild ponies and Osprey nests. Williamsburg is a 1 1/2 hour drive; a perfect day trip. Experience a slower pace of life with access to all the fun you want.
Note: The pool is open for Memorial Day. Please let me know if you'd like it opened earlier in the season.
Please note: Loud music and parties are not tolerated. This is a very quiet, peaceful community, and excessive noise is not tolerated. Thank you for your understanding and acceptance of this condition.
Amenities
Pool
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
Hot tub or spa
Garden
Family friendly
Map of Chesapeake Bay, NC
Reviews
4.8
Outstanding(36 Reviews)4.8
We’ve stayed in quite a few home rentals. This house was the most well stocked home we’ve ever stayed in. What a lovely home and the pool was great. Unfortunately, Tropical Storm Debby passed by during our stay, but we found things to do and enjoyed ourselves. We highly recommend this home. Thanks to Jack for a great time.
4.8
This house was great! It had every amenity we needed including sheets, bath towels, and pool towels. The layout worked well as there is one bedroom on the first floor for anyone who needs to stay away from stairs. It was large enough for us to enjoy each other or quiet times on our own. The beach is a trek but not un-doable. We took two beach umbrellas (provided) and all the beach chairs we needed. The whole environment of the home and neighborhood had something for everyone. We bbq'd almost everyday. The guys went crabbing at Kiptopeke State Park and brought back enough crabs for all to enjoy for dinner that night. I loved this house and all it offered!
4.8
As a family of 8 adults and 2 young children, we needed a spacious house with plenty of outdoor space to allow for a comfortable week’s vacation in Cape Charles. Jack’s place was perfect for all of our needs, with plenty of bedrooms and bathrooms, an exceptionally well equipped kitchen and an expansive back yard with a multi layered deck, and a salt water pool. Jack was attentive to all of our questions and inquiries. The access to a quiet sandy beach mins from the house was an added bonus for all. The calm water was ideal for our 3 year old grandson and all the adults enjoyed lengthy shoreline strolls, as well as watching dolphins playing in the waves and even a bald eagle sighting ! We all enjoyed the peaceful setting of the area, with plenty of cheery bird song to greet us in the morning and send us to sleep in the evenings We count ourselves very lucky to have found this little piece of paradise in Cape Charles.
4.8
Super layout for our large family. The pool was excellent for the children when having down time from the beach. Most peaceful setting yet close enough drive to Cape Charles for all our excursions. Jack is a very kind and hands on host. Will definitely use this property again.
4.8
We knew the Pool would be the highlight and it was!! But So Much More to enjoy:-) The Beach, the well equipped home, outdoor area, garage, beautiful landscape, peaceful area and Cape Charles town. Everyone in the Family from youngest to oldest Really had a Great Time!!!
4.8
We had great vacay! We were a group of
7 adults and 4 kids. The house was well equipped! Loved the new gas range! The living space was great to allow people space! It was broken up nicely with two dinning spaces and three sitting areas. Beds were comfy! The garage was well equipped with beach items and chairs! Honestly, they thought of everything! From garbage bags, spices, to beach chairs! The backyard is an oasis! Beautiful pool, lounging areas, and lots of green space.
Only concern is that you need to be extremely quiet outside. No music, no kids playing, no loud noises. Unfortunately the neighbors complained, and we were very sensitive to all noise outside after that.
Cape Charles is a cute town! We checked out the beach there mutliple times. Loved the breweries, shops, mini golf, ice cream, and checked out a few restaurants! Definitely check out A1 Seafood Market.
4.8
A few housekeeping items that could be addressed (such as eradicating sugar ants and better cleaning of the bathrooms) and more comfortable seating in the den for more to watch the one TV there but overall it was a very enjoyable stay. Our grandkids had a great time in the pool and it was a very relaxing vacation.
4.8
We enjoyed our stay at Jack’s property! It was peaceful and relaxing.
+ Pool was very nice, clean, good size
+ Entire backyard with gazebo, lounge chairs, tables were great to hang out. We ate all of our meals out there
+ Wraparound porch with rocking chairs was lovely for sitting and enjoying the pretty landscaping
- Beach access was difficult. Have to walk through a stretch of woods, and the golf cart rental places in town don’t allow you to take them all the way out to this community because of the highway. So we had to carry all of the chairs and umbrellas ourselves
- Beach items were on the older side and there weren’t many toys for the kids (buckets, shovels, etc.)
- Freezer wasn’t in great shape in terms of cleanliness
4.8
Great family vacation
We had a great stay at Jacks. We’re a multigenerational group that travels together each summer. The pool was great although there were some issues w the filter. Jack was very communicative about the issues. The location near the private beach was great. We loved riding bikes or driving over for mornings/evenings on the beach. It was a great stay!
4.8
Relaxing vacation
We were very pleased with this property. There was plenty of room for everyone. We loved having our own pool and backyard for the kids to play. Everything was clean and host had quick responses to any questions we had. I would definitely rent this place again! Thanks Jack!!
4.8
Cape Charles away from the madding crowd
Loved being able to go to the beach in the morning and come back to the house for the little ones to nap and the older kids to play in the pool and yard. Perfect situation for our group
4.8
Family vacation 2021
The property was perfect for a family, the house was equipped with everything you could want. I was a little shocked that there was not much to do in the area. Renting golf carts would have been fun but you need to reserve them in advance there was nothing available for the entire week. So if you want to relax and swim then this is the perfect place.
4.8
An amazing property, the house had everything we needed and more to provide a perfect and much relaxing week for our annual summer family vacation (12 people total; 3 families with children). House was clean, roomy and we much appreciated the fully stocked kitchen and grill to prepare meals every evening. The kids loved playing in the pool, large backyard and swing set all week. The private beach is fantastic, we had no issues driving and getting gear out the path to the beach with the cart and wagon that were provided. Amazing sunsets over the bay every evening and the water was mostly calm which was great for small kids.
Jack is an excellent host and provided all the information that you could need up front, and was very responsive to questions we had prior to the trip.
It was our first time to Cape Charles which is a wonderful town. We made frequent trips to browse the shops on main street, grab lunch at some great restaurants (Kelly's Pub & Dead Rise Pies), and also spent an afternoon at the beach in town and fishing pier.
4.8
We have been coming to Cape Charles with our family to visit for the past few summers. Each time we have rented this property. It is a large and comfortable home with plenty of amenities and one of few homes in Cape Charles with its own private pool. The house comes with plenty of backyard activities and board games that families can enjoy together. The beach access is not a bad bicycle ride or a quick car ride. There is a light 5 minute walk through some greenery after parking your car. I think next time we will rent a golf cart to easily transport our beach gear. The private beach is worth the walk. The owner was very kind and had a very fast response.
4.8
We have been coming to Cape Charles with our family to visit for the past few summers. Each time we have rented this property. It is a large and comfortable home with plenty of amenities and one of few homes in Cape Charles with its own private pool. The house comes with plenty of backyard activities and board games that families can enjoy together. The beach access is not a bad bicycle ride or a quick car ride. There is a light 5 minute walk through some greenery after parking your car. I think next time we will rent a golf cart to easily transport our beach gear. The private beach is worth the walk. The owner was very kind and had a very fast response.
4.8
Quiet Family Getaway
We have been coming to Cape Charles with our family to visit for the past few summers. Each time we have rented this property. It is a large and comfortable home with plenty of amenities and one of few homes in Cape Charles with its own private pool. The house comes with plenty of backyard activities and board games that families can enjoy together. The beach access is not a bad bicycle ride or a quick car ride. There is a light 5 minute walk through some greenery after parking your car. I think next time we will rent a golf cart to easily transport our beach gear. The private beach is worth the walk. The owner was very kind and had a very fast response.
4.8
An amazing property, the house had everything we needed and more to provide a perfect and much relaxing week for our annual summer family vacation (12 people total; 3 families with children). House was clean, roomy and we much appreciated the fully stocked kitchen and grill to prepare meals every evening. The kids loved playing in the pool, large backyard and swing set all week. The private beach is fantastic, we had no issues driving and getting gear out the path to the beach with the cart and wagon that were provided. Amazing sunsets over the bay every evening and the water was mostly calm which was great for small kids.
Jack is an excellent host and provided all the information that you could need up front, and was very responsive to questions we had prior to the trip.
It was our first time to Cape Charles which is a wonderful town. We made frequent trips to browse the shops on main street, grab lunch at some great restaurants (Kelly's Pub & Dead Rise Pies), and also spent an afternoon at the beach in town and fishing pier.
4.8
Excellent home for our family summer vacation
An amazing property, the house had everything we needed and more to provide a perfect and much relaxing week for our annual summer family vacation (12 people total; 3 families with children). House was clean, roomy and we much appreciated the fully stocked kitchen and grill to prepare meals every evening. The kids loved playing in the pool, large backyard and swing set all week. The private beach is fantastic, we had no issues driving and getting gear out the path to the beach with the cart and wagon that were provided. Amazing sunsets over the bay every evening and the water was mostly calm which was great for small kids.
Jack is an excellent host and provided all the information that you could need up front, and was very responsive to questions we had prior to the trip.
It was our first time to Cape Charles which is a wonderful town. We made frequent trips to browse the shops on main street, grab lunch at some great restaurants (Kelly's Pub & Dead Rise Pies), and also spent an afternoon at the beach in town and fishing pier.
4.8
Wonderful, Relaxing vacation
We had a wonderful week staying in Cape Charles. The home fit all of our needs. It was clean, spacious and beautifully decorated. We also really appreciated the well stocked kitchen. After a hot day at the beach, coming home to a pool was just what we all needed. Great home!
4.8
Thanksgiving gathering
What a lovely home! We took our household to Cape Charles to meet up with one of our adult kids and had the most relaxing time. I was nervous about cooking Thanksgiving in a strange kitchen but everything I needed was there (I brought a roaster for the turkey). We were blessed with wonderful weather and walked to the beach every day (sometimes more!) to enjoy watching the dolphins, exercising and just relaxing. We ate outdoors at several local places (The Shack and Cape Charles distillery) - both excellent. Played corn hole and binged some Netflix too. Exactly the get away that we all needed. The House is in a very rural neighborhood (but oh the sunshine that streams through all the windows!) and the beach is about 3/4 mile but there are beach wagons in the garage if you need to haul stuff there. I ordered groceries ahead at Wegmans in Va Beach and they were ready for pickup as we arrived. Thanks for sharing your home with us!
4.8
Beautiful Remote Property
This was a beautiful property in a very remote location, which was just what we were looking for. The pool was amazing and the owners provided everything you could need, including for small children. There's so much nature to look at on the property- butterfly bushes, a fig tree, lizards, spiders, deer, swallows' nests and rabbits. Definitely bring some bug spray if you plan to hang outside at night time.
The beach is private and pristine, but I would definitely recommend renting a golf cart for the week. It's a 3 min drive or 10 minute walk to the path, but then it's another 5-10 min walk down the path to the beach. Be aware that on the sides of the path we saw poison sumac and poison ivy (this has nothing to do with the property owners). It's totally worth the journey though. The bay was calm and provided more beautiful nature, including ghost crabs, sand pipers, seagulls, hermit crabs, etc.
Overall it was a great stay and I would recommend it to any nature lover.
4.8
Great spot for the family
Between the pool and access to the beach, this was a great place to stay with our three kids. They were constantly entertained.
4.8
Great spot for a family vacation
We had a great week for a family vacation the property is located between Cape Charles and the bay bridge tunnel for easy access to Virginia Beach and Cape Charles The pool was great the house had every you could need Great property I would definitely rent this property again
4.8
Great value rental home! Spacious and secluded!
Our family of 11, 7 adults and 4 kids, had a great time for our week at the house. There was plenty of room for all of us, with a fantastically equipped kitchen with everything that you could need. All rooms and amenities were well kept and up to date. The pool and outside area were perfect for the little ones to enjoy, and the adults too!
The private beach was a bit farther than we had believed as it wasn't walking distance from the house, but it was still fun. The public beach (15 minutes) and Virginia Beach (40 minutes) were not far drives. There were plenty of beach chairs and many kinds of beach items at the house.
The small town is very quaint, we really enjoyed dinners at the Shanty and Kelly's Pub, and ice cream at Brown Dog Ice Cream!
The owner was very reachable, we had one small issue and he got back to us within 10 minutes and easily resolved the issue.
We had a great time, and would definitely recommend this home for your summer vacation!
4.8
Our family of 11, 7 adults and 4 kids, had a great time for our week at the house. There was plenty of room for all of us, with a fantastically equipped kitchen with everything that you could need. All rooms and amenities were well kept and up to date. The pool and outside area were perfect for the little ones to enjoy, and the adults too! The private beach was a bit farther than we had believed as it wasn't walking distance from the house, but it was still fun. The public beach (15 minutes) and Virginia Beach (40 minutes) were not far drives. There were plenty of beach chairs and many kinds of beach items at the house.The small town is very quaint, we really enjoyed dinners at the Shanty and Kelly's Pub, and ice cream at Brown Dog Ice Cream!The owner was very reachable, we had one small issue and he got back to us within 10 minutes and easily resolved the issue.We had a great time, and would definitely recommend this home for your summer vacation!
4.8
Beautiful Eastern Shore get away for the whole family
Our family, three generations completely enjoyed our stay in this Cape Charles lovely home . The owner literally thinks of everything! The house was beautiful, the pool was pristine, and the nearby private beach was absolutely gorgeous. There were kayaks to go kayaking, several bicycles and so many amenities included in the house. The beds were super comfortable, various sitting room areas, with a beautiful fenced in backyard and we had everything we could think of in the kitchen to make some memorable meals. Highly recommend staying here! If we vacation on the Eastern Shore again, this is where we will stay!
4.8
Perfect home for a family vacation!!!!
Our family was VERY impressed with the home. The owner was prompt to remedy any problems, which there were few of. The home was convenient to all we wished to experience, while being private enough to avoid the usual tourist hustle and bustle. We have already discussed returning to this fabulous Family retreat. Thank you Jack for maintaining such a lovely and well stocked retreat.
4.8
Once again we had an amazing family vacation. There is plenty of space both inside the home and outside.
4.8
It's wonderful house
This is a wonderful house it's like my own house whatever I need it's there for me all kitchenette abundantly nice pool beautiful private beach but only the problem when i stay was the sink problem (leaking) but I understand cause holiday is hard to find a plumber if it was fix this is gonna be perfect for everything and like a dream house
4.8
The Perfect Getaway
Once again we had an amazing family vacation. There is plenty of space both inside the home and outside.
4.8
We enjoyed our week. The house was well equipped for a multi-generational family. The space was nice and the house was clean and ready to use. The proximity to Cape Charles was nice and the restaurants were good. Enjoyed walking around town. We enjoyed the area and the house enough that we will consider coming back.
Would definitely recommend the location.
The farmer's market was a bit disappointing. There were only a couple of vendors ...and only 3 with fresh produce. Was expecting to find fresh corn and there was none to be had, which was surprising given all the farms in the area.
Only had two issues, neither major deals but worth noting. The recycling from the former renters was never picked up. It was overflowing the can and left us no place to put our recycling. We has such a quick response when we needed the pool water cleaned up (it turned green), we were surprised that nothing was done with the trash.
There was more than one tank of fuel for the grill but they were all empty! That was frustrating. We were in the middle of cooking our dinner when the tank on the grill ran out. We decided not to call since we were still waiting for the recycling issue to be resolved and figured by the time some one would be able to come with a full tank, it would be too late. Would recommend making sure at least one tank is full for new renters.
Overall it was a relaxing and enjoyable week.
4.8
Overall the rental was great. We loved the pool and the closeness of the ocean.
We enjoyed our week. The house was well equipped for a multi-generational family. The space was nice and the house was clean and ready to use. The proximity to Cape Charles was nice and the restaurants were good. Enjoyed walking around town. We enjoyed the area and the house enough that we will consider coming back.
Would definitely recommend the location.
The farmer's market was a bit disappointing. There were only a couple of vendors ...and only 3 with fresh produce. Was expecting to find fresh corn and there was none to be had, which was surprising given all the farms in the area.
Only had two issues, neither major deals but worth noting. The recycling from the former renters was never picked up. It was overflowing the can and left us no place to put our recycling. We has such a quick response when we needed the pool water cleaned up (it turned green), we were surprised that nothing was done with the trash.
There was more than one tank of fuel for the grill but they were all empty! That was frustrating. We were in the middle of cooking our dinner when the tank on the grill ran out. We decided not to call since we were still waiting for the recycling issue to be resolved and figured by the time some one would be able to come with a full tank, it would be too late. Would recommend making sure at least one tank is full for new renters.
Overall it was a relaxing and enjoyable week.
4.8
Beautiful property....Home sweet Home!
Great home and vacation experience! We built awesome memories with our family and had a great time. Pool was fun, deck was very nice, great family atmosphere. Only caveat, the grill do not work and the outdoor speakers that were advertised were not working. The beach was a little far away, and a bit of a hassle to get all of your things there due vehicles not be able to drive to the beach. However, we didn't let it put a damper on our family barbecue and we were able to improvised.
4.8
Family of five just spent a blissful week at this wonderful spot. House is incredibly well appointed - plenty of kitchenware, linens, pool toys, bikes and games - truly outstanding for a house rental. Each room is well decorated and there's tons of space - ideal for my two teenagers and two year old. It would be perfect for large gatherings. Access to the private beach meant we had a bit of Chesapeake Bay all to ourselves, and back at home a large pool and deck and yard to relax in. The surrounding farmlands offered stunning views at all times of the day, and the quiet roads were perfect for peaceful bike riding. Nearby Cape Charles has all the charm a beach town needs - with plenty of restaurants (including a not to miss ice cream parlor), a farmer's market, up-to-date playground, historic movie theater and shopping. This is a lovely spot, and highly recommended.
4.8
Fantastic House in Gorgeous Setting
Family of five just spent a blissful week at this wonderful spot. House is incredibly well appointed - plenty of kitchenware, linens, pool toys, bikes and games - truly outstanding for a house rental. Each room is well decorated and there's tons of space - ideal for my two teenagers and two year old. It would be perfect for large gatherings. Access to the private beach meant we had a bit of Chesapeake Bay all to ourselves, and back at home a large pool and deck and yard to relax in. The surrounding farmlands offered stunning views at all times of the day, and the quiet roads were perfect for peaceful bike riding. Nearby Cape Charles has all the charm a beach town needs - with plenty of restaurants (including a not to miss ice cream parlor), a farmer's market, up-to-date playground, historic movie theater and shopping. This is a lovely spot, and highly recommended.
4.8
Amazing home!
We are just in our second day here and are so impressed. Jack pays attention to every detail! I have stayed at quite a few vacation homes over the years. This is a place where you can relax, enjoy the outdoors, cook etc., without bringing everything from home to do so! The kitchen is equipped beautifully with much more available than I ever expected! The pool and home are beautiful, incredibly comfortable beds, and a beautiful yard. You won't be disappointed.
4.8
Extended family stayed here in September. While attending a family wedding in Cape Charles. The home and property was absolutely beautiful! Jack the owner was so helpful. We hosted the rehearsal dinner/BBQ here. He helped us arrange additional parking for our guests. He provided directions for family members and recommended activities. The beach was pristine although a little further away than we expected (about a2-3 minute drive to access and another few minutes walk). It was absolutely worth it once you got there. The home has lots of additional amenities as well. Many beach toys and bicycles etc... Plenty to do for all ages.
4.8
Lovely property with a wonderful owner!
Extended family stayed here in September. While attending a family wedding in Cape Charles. The home and property was absolutely beautiful! Jack the owner was so helpful. We hosted the rehearsal dinner/BBQ here. He helped us arrange additional parking for our guests. He provided directions for family members and recommended activities. The beach was pristine although a little further away than we expected (about a2-3 minute drive to access and another few minutes walk). It was absolutely worth it once you got there. The home has lots of additional amenities as well. Many beach toys and bicycles etc... Plenty to do for all ages.
4.8
We loved all the opportunity for outdoor activities such as biking and going to the beautiful beach. We were a bit disappointed that a few of the bikes needed maintenance and were essentially unusable, the pool did not have a working light and was not functional at night and a few areas around the house needed maintenance such as the broken umbrella on the deck, grill was out of propane, and a hole in the wall in bedroom. Also, the beach passes were missing and the neighbor/owners were very unwelcoming when we parked our car at the beach entrance to drop off older members of our group as a result. That was unfortunate since we came to the area specifically to see if it might be a great retirement/vacation home spot for the in-laws. We would give this stay a five if those concerns were addressed. All in all, it was a fun vacation and we liked the lovely house and gardens.
4.8
Beautiful Beach and Wonderful Outdoor Activities
We loved all the opportunity for outdoor activities such as biking and going to the beautiful beach. We were a bit disappointed that a few of the bikes needed maintenance and were essentially unusable, the pool did not have a working light and was not functional at night and a few areas around the house needed maintenance such as the broken umbrella on the deck, grill was out of propane, and a hole in the wall in bedroom. Also, the beach passes were missing and the neighbor/owners were very unwelcoming when we parked our car at the beach entrance to drop off older members of our group as a result. That was unfortunate since we came to the area specifically to see if it might be a great retirement/vacation home spot for the in-laws. We would give this stay a five if those concerns were addressed. All in all, it was a fun vacation and we liked the lovely house and gardens.
FAQs
How much does this house cost compared to others in Chesapeake Bay?
The average price for a rental in Chesapeake Bay is $375 per night. This rental is $834 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Family vacation retreat w/ In-ground Pool with private Chesapeake Bay access!. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
Yes, a swimming pool is available for use at Family vacation retreat w/ In-ground Pool with private Chesapeake Bay access!. Enjoy the water!
Is Family vacation retreat w/ In-ground Pool with private Chesapeake Bay access! pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Family vacation retreat w/ In-ground Pool with private Chesapeake Bay access!?
We found 11 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and parking.
Explore similar vacation rentals in Chesapeake Bay
Explore all rentals in Chesapeake BayStart earning One Key rewards
Award Winning Ocean Front Architectural Gem [Home Share per VA Beach Zoning]
House
in Virginia Beach12 guests · 4 bedrooms · 6 baths
Garden · Pool · Pets allowed
This House in Chesapeake Bay, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
Start earning One Key rewards
Inchgarth at Scotland Yards
House
in Scotland14 guests · 7 bedrooms · 6 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
Nestled in Chesapeake Bay, this House is perfect for your next vacation. Enjoy Inchgarth at Scotland Yards's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Spacious Luxury 6 BR Home, Sleeps 15, Private Pool, In Nature, Convenient to DC
House
in Harwood15 guests · 6 bedrooms · 6 baths
Garden · Pool · Kitchen or Kitchenette
This House in Chesapeake Bay, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
Historic Beach Front Home: Victorian Elegance. Large Rooms with AMAZING bay view
House
in Cape Charles12 guests · 5 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette
Looking to create some memories in Chesapeake Bay? Look no further than our House, Historic Beach Front Home: Victorian Elegance. Large Rooms with AMAZING bay view. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Charming Annapolis Victorian
House
in Annapolis12 guests · 6 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking to create some memories in Chesapeake Bay? Look no further than our House, Charming Annapolis Victorian. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
House
in Woolford18 guests · 7 bedrooms · 5 baths
Garden · Pool · Pets allowed
Indulge in a peaceful retreat at Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock, our elegant House in Chesapeake Bay. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool
House
in Cambridge17 guests · 6 bedrooms · 5 baths
Garden · Pool · Pets allowed
Indulge in a peaceful retreat at Peaceful Waterfront Retreat ~ 23 Private Acres With Dock & Pool, our elegant House in Chesapeake Bay. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
House
in Rock Hall14 guests · 6 bedrooms · 4 baths
Pool · Kitchen or Kitchenette · Air conditioner
Experience the best of Chesapeake Bay with this House available for $1,330. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
When you want to get away from everything Magnolia shores 2 acres of tranquility
House
in Reedville18 guests · 8 bedrooms · 6 baths
Garden · Pool · Kitchen or Kitchenette
This attractive House in Chesapeake Bay, $1,195 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
PET FRIENDLY-BEAUTIFUL APPOINTED HOME WITH BAY VIEWS AND PRIVATE COMMUNITY BEACH
House
in Cape Charles14 guests · 5 bedrooms · 5 baths
Pool · Pets allowed · Kitchen or Kitchenette
House in Chesapeake Bay, for $1,103 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
A Vacation Away From It All-Family And Pet Friendly
House
in Taylors Island12 guests · 5 bedrooms · 5 baths
Garden · Pets allowed · Kitchen or Kitchenette
Experience vacation in Chesapeake Bay with our House, A Vacation Away From It All-Family And Pet Friendly. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Multi-Generational Waterfront Retreat with Pool. No cleaning fees!
House
in Cambridge12 guests · 4 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner
House in Chesapeake Bay, for $1,174 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Start earning One Key rewards
Stunning Annapolis Home! Across from the library, walk to Naval Graduation
House
in Annapolis12 guests · 5 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Stunning Annapolis Home! Across from the library, walk to Naval Graduation for $1,309 for your next trip.
$$$$
Start earning One Key rewards
Breath-Taking Family Retreat On The Water!
House
in Upper Fairmount24 guests · 8 bedrooms · 4 baths
Kitchen or Kitchenette · Air conditioner · Parking
Discover the beauty of Chesapeake Bay with a stay at Breath-Taking Family Retreat On The Water! , a top rated House with amenities such as Air conditioner, Dishwasher and Laundry, and more.
$$$$
Beachfront
Coastal Bliss: 3500 sqft Beachfront Haven, Steps Away from Your Private Beach - Your Ultimate Cape Charles Getaway
House
in Cape Charles15 guests · 6 bedrooms · 5 baths
Garden · Pets allowed · Kitchen or Kitchenette
Looking for a memorable stay in Chesapeake Bay? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.
$$$$
Renovated Historic Waterfront Home with Pool, Dock, 200 acres
House
in Cambridge18 guests · 7 bedrooms · 5 baths
Garden · Pool · Pets allowed
Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Chesapeake Bay, at $1,262 per night for your next great vacation.
$$$$
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
House
in Chesapeake City15 guests · 7 bedrooms · 7 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Are you ready to indulge in a relaxing getaway? Our House in Chesapeake Bay has everything you need for a rejuvenating stay. Treat yourself to Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows 's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
$$$$
Front Row Ocean View! 6 Beds! 5 Decks, 4 Baths! Rec Room, Kayaks! Go Coastal!
House
in Norfolk12 guests · 5 bedrooms · 4 baths
Garden · Pool · Pets allowed
This attractive House in Chesapeake Bay, $982 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Start earning One Key rewards
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
House
in Cambridge12 guests · 6 bedrooms · 3 baths
Garden · Pool · Pets allowed
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach for $1,440 for your next trip.
$$$$
5 acre estate with deep water dock and 1,700 feet of shoreline
House
in Rock Hall14 guests · 5 bedrooms · 3 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
This House for $982 in Chesapeake Bay, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Bay Creek Home Close to Private Beach, Pool & Golf
House
in Cape Charles15 guests · 5 bedrooms · 5 baths
Garden · Pool · Kitchen or Kitchenette
Enjoy the best of Chesapeake Bay in our House, Bay Creek Home Close to Private Beach, Pool & Golf. A stunning property with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
House
in Cambridge16 guests · 5 bedrooms · 4 baths
Pool · Pets allowed · Kitchen or Kitchenette
Soak up the beauty of Chesapeake Bay in our House, Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Start earning One Key rewards
Waterfront Paradise Located on Virginia's Beautiful Eastern Shore (boat slip)
House
in Onancock12 guests · 5 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette
The best choice in Chesapeake Bay for House, for $1,081 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Start earning One Key rewards
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
House
in Stevensville14 guests · 5 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner
This House in Chesapeake Bay, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
Start earning One Key rewards
Waterfront Scotland Beach Retreat w/ Private Beach
House
in Ridge12 guests · 6 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Top rated
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Waterfront Scotland Beach Retreat w/ Private Beach for $1,050 for your next trip.
$$$$
Beachfront
Gorgeous 6 Bed, 5 Bath Beachfront Home With Private Beach!
House
in Cape Charles12 guests · 6 bedrooms · 5 baths
Kitchen or Kitchenette · Air conditioner · Parking
Experience the best of Chesapeake Bay with this House available for $1,148. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Historic Stepne Manor on Maryland's Eastern Shore
House
in Chestertown15 guests · 5 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette
Discover the beauty of Chesapeake Bay with a stay at Historic Stepne Manor on Maryland's Eastern Shore, a top rated House with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Beachfront
Privacy & tranquility at Beauty on the Beach, Beachfront!
House
in Cape Charles12 guests · 5 bedrooms · 5 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Looking for the perfect place to call home during your trip to Chesapeake Bay? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
House
in Tracys Landing16 guests · 5 bedrooms · 6 baths
Garden · Pool · Pets allowed
Experience the best of Chesapeake Bay with this House available for $1,204. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Waterfront River Breezes with private pier, parking and billiards room
House
in Severna Park13 guests · 4 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Waterfront River Breezes with private pier, parking and billiards room for $1,174 for your next trip.
$$$$
Chesapeake Bay travel inspiration
Read our blogGuides
Top Things to Do in Miami: From Beaches to Culture
Guides
The Best Things to Do in Orlando: Attractions, Food, and Family Fun
Guides
Things to Do in Galveston, Texas
Guides
Top Things to Do in Myrtle Beach
Guides
Ski Trip Packing List: What to Bring Skiing or Snowboarding
Trends
VacationRenter Holiday Travel Trends 2023
Featured Rentals
Architectural Vacation Rentals: Experience the Beauty of Unique Properties
Featured Rentals
Sustainable and Eco-Friendly Vacation Rentals Around the World