PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline
House in Chesapeake Bay, NC
12 guests · 5 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
Top-tier experienceOne of the higher cost properties in the area
About this house rental
Beach front home with over 1 acre yard. Beautiful views of the Chesapeake Bay from almost anywhere you stand. Large deck and gazebo for evening gatherings or sit on the separate, private, beachfront deck to watch dolphins, blue heron and eagles play. Watch the sunrise from the furnished roof deck. Enjoy your beverage of choice before laying your towel or setting your chair on the white sand beach to soak up some sun. Tired of sitting, check the crab pots, throw in a fishing line or grab one of the two kayaks and take a journey around the island or watch the sail boat regattas that take place on most summer weekends. Plenty of room for the kids to run and play in the expansive, private yard.
This home has it all....open floor plan, large sun room, dining area and wet bar. 5 bedrooms, 1 King, 4 Doubles, 3 twins and one murphy bed in a large bedroom that doubles as a second den for the little ones or the teenagers who want their space. 3 full bathrooms, and a large yard to play outside games including corn hole which is provided and a basketball goal. Spacious kitchen with breakfast bar and dual ovens. Two large smart TV's, satellite service and strong Wi-Fi keep you connected if that's your "thing". The house has two detached garages, one of which is available for storage and also contains beach toys including two kayaks and some fishing equipment, crab pots and rafts as well as an additional refrigerator. Automatic whole house generator so you will never lose power during a possible summer thunderstorm. Nights can be spent on the sand beach or on the expansive deck or the newly added roof deck. It its raining make yourself at home under the lighted gazebo. Also, in the gazebo is a large gas grill and teak table and chairs. A fire pit with supplied firewood provides a great area for gathering as well. Saturday mornings during the summer, you can find local grown items at the farmers market on the courthouse green located at Matthews Courthouse. While there, be sure to visit some of the quaint shops to find that unique gift or get a bite to eat at one of the many local restaurants throughout the courthouse area. If this is your first visit stop by the Information Center located next to the library. Also, go to our points of interest in this special town.
Historic Yorktown, Jamestown and Colonial Williamsburg are about an hour away. If history is not your thing, a day trip to visit Busch Gardens or Water Country is about the same distance. ***Minimum 7 nights stay last week in May through Labor Day weekend. Requests for shorter stays outside of these dates may be accepted on a case-by-case basis.***
Your perfect vacation awaits!
This home has it all....open floor plan, large sun room, dining area and wet bar. 5 bedrooms, 1 King, 4 Doubles, 3 twins and one murphy bed in a large bedroom that doubles as a second den for the little ones or the teenagers who want their space. 3 full bathrooms, and a large yard to play outside games including corn hole which is provided and a basketball goal. Spacious kitchen with breakfast bar and dual ovens. Two large smart TV's, satellite service and strong Wi-Fi keep you connected if that's your "thing". The house has two detached garages, one of which is available for storage and also contains beach toys including two kayaks and some fishing equipment, crab pots and rafts as well as an additional refrigerator. Automatic whole house generator so you will never lose power during a possible summer thunderstorm. Nights can be spent on the sand beach or on the expansive deck or the newly added roof deck. It its raining make yourself at home under the lighted gazebo. Also, in the gazebo is a large gas grill and teak table and chairs. A fire pit with supplied firewood provides a great area for gathering as well. Saturday mornings during the summer, you can find local grown items at the farmers market on the courthouse green located at Matthews Courthouse. While there, be sure to visit some of the quaint shops to find that unique gift or get a bite to eat at one of the many local restaurants throughout the courthouse area. If this is your first visit stop by the Information Center located next to the library. Also, go to our points of interest in this special town.
Historic Yorktown, Jamestown and Colonial Williamsburg are about an hour away. If history is not your thing, a day trip to visit Busch Gardens or Water Country is about the same distance. ***Minimum 7 nights stay last week in May through Labor Day weekend. Requests for shorter stays outside of these dates may be accepted on a case-by-case basis.***
Your perfect vacation awaits!
Amenities
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden
Family friendly
Map of Chesapeake Bay, NC
$$$$
Reviews
5.0
When we arrived the owners were there adding a few last minute amenities based on someone’s feedback and they were very welcoming and approachable. The pictures don’t do the home justice, the views from the sunroom and deck are amazing. The beds were very comfortable and the kitchen was well equipped. The beach was nice and sandy and my children loved playing in the water. My husband enjoyed the kayak. We love Gywns Island and have stay
5.0
We had a gorgeous week's stay. We had such a good time we asked to stay an additional day, which they were able to accommodate. Days were filled with swimming, kayaking and crabbing. We caught so many keeper crabs that we threw a dozen back.
5.0
Beautiful surroundings. Very quiet. About 45 minutes to tourist attractions. Nice family accommodations.
4.0
Nice yard and outdoor activities, lots of room to run around with the grandkids. Room to spread out in the house for all. Nice private beach area. Only problem was the jelly fish, not sure why there was so many, but we had fun anyway building sand castles and trying to catch crabs. Owner very responsive, first day there were ants in the kitchen, Bryan brought ant traps over right away and that took care of the problem. The kayaks were used every day
5.0
We had an amazing week went to Busch Gardens 2 days which was an hour away. Only issue was there were hundreds of jellyfish in the water. But we made the best of it. The kayaks were great.
5.0
This was an amazing place! We have a family of 8 and we fit very comfortably!! We had fun swimming, fishing, playing corn hole and kayaking. Loved having extra fridges in the garage! Brian was a great host!! He communicated very well and quickly!!
5.0
Incredible spot and exactly what we were looking for. Private, quaint with everything needed for three generations of family. Host is very responsive and helpful. Will be back!
5.0
Beautiful property in a peaceful rural community. Private beach cinches the deal for families with small children.
5.0
This was our second stay in this home. It is right on the bay with a small, well protected beach. All we needed was provided, including a very well stocked kitchen, beach chairs, kayaks, puzzles, games, and more. The open floor plan was wonderful for family dinners and hang time. Loved our stay and will definitely be back!
5.0
13 of us in our Old Farts Camp Out group since 2005 ... from Bristol to Front Royal and points Northern & Central Va. Our Winter Rendezvous of old Scouters, BSA dads, and former Scoutmasters were impressed with the location on the water. Communication prior to our rental was quick and very helpful. Lodging details from entry to exit were very detailed. Plenty of linens, blankets, towels, kitchenware, tools, supplies, and accessories. Small commercial icemaker was a great extra. Decor is pleasing. Plenty of room for our game tables. Little disappointed that the gas fireplace was inoperable, but the firepit with logs from the woods and the sun in the front room and on the decks... was more than enough. We just soaked in the view using plenty of table, gazebo and deck chairs available. We stayed on the Island the entire weekend with a visit to a fantastic little museum that accommodated our off season visit... just had to give advanced notice so Tom could open up and help us around. The little waterside Hole In The Wall cafe diner was quite the experience with an accommodating staff for our odd size troop... fine enough meal with a good choice of beers, burgers and bayfood. Parking is primo plenty. We would return for our summer gathering, but can't quite get a full week with so many still working. Thanks much to the Grizzard Hosts.
5.0
We had everything we needed to be able to relax and enjoy being together.
5.0
We had a wonderful time at this property for the Thanks giving. We enjoyed the ocean view and sunrise. Summer time will be fantastic as there is good space and opportunity to be used for outdoor activities. We felt little crunched for bath room use downstairs as many sleep here and only one bath available. The island itself is nice and people are nice. The nearest gas station and grocery shop is 4 miles. Carry extra paper towels, toilet tissues as there was only bare minimum. Host was excellent, he lommunicated with precision on my quiries. I would recomend this place to large group of family gathering.
4.0
We had a group of 11 people ranging in ages from 68- 2. Someone was always kyacking or catching crabs,playing in the sand or swimming. Everyone had adequate space and comfortable beds. It is a great place to go back and forth to the beach and worked well for our extended family. There was room for all of us to be together and space to spread out. We enjoyed star gazing from the balcony.
5.0
I stayed here with 12 other friends for a joint bachelor/bachelorette party and we all felt the pictures didn’t do this place justice. It was clean and spacious, and the water view was beautiful. Many of us would get up for sunrise and go to the beach with our coffees. I appreciated the amount of things that came with home, such as kayaks and cooking pots. There were more rocks in the water than expected so we had a few stubbed toes. Otherwise it was a beautiful beach. Would definitely stay here again.
5.0
The property was perfect for a week with our large family we had 10 adults and 2 children fit comfortably there was plenty of room inside and outside to relax and enjoy the beautiful weather. The beach was private and large. Everything was wonderful. The neighboring properties were vacant during our week which really made it private. I do think if there were groups like ours staying on either side of the house it would have made our week much less enjoyable.
5.0
The property is beautiful! The vacation rental is very nice; we’ve stayed at the house I think two other times! Maybe could use a few upgrades but not absolutely needed!
We had a beautiful view with beautiful weather!
We love the Island! It’s so peaceful, quiet and relaxing!! Hope to return in 2024!!
5.0
Perfect location for my brother's celebration of life. Woke up every morning to watch the dolphins jumping and shooting stars at night. Absolutely Amazing!
5.0
Our second stay at this beautiful home did not disappoint. Lovely and spacious house and yard with a private beach to swim, play in the sand, fish and kayak. Breathtaking views and a quiet neighborhood. Gwynn and Mathews are the coolest little towns and everyone is so welcoming. We are becoming very fond of Gwynn’s Island and plan to return!
5.0
I could not recommend this place more - peaceful, pristine, perfect for any age. We will be back!
5.0
This was a perfect vacation home for our family. There was plenty of space inside and it was very nicely furnished. There are many outside areas , a deck off the living area, a gazebo and a second floor deck , all of these have a beautiful view of the river. There is great beach access. We spent our sunny days swimming , kayaking and watching the dolphins. The owner was very responsive and helpful. This is definitely the best stay on the River!
5.0
Sunrises and peaceful bay vacation
5.0
I can’t say enough about how perfect this house was for us. There were 8 adults plus a baby, and we had room to be together and room to be apart. The location is extremely private and stocked with every game and activity to keep us all entertained!
Our favorites were the outdoor shower, kayaks, and private beach.
The biggest win was the amazing owner responsiveness. When I texted with a concern, he immediately responded and went above and beyond to ensure our comfort.
We will definitely book again!
5.0
We were looking for a good location for a leadership retreat and this was a great option. We were able to handle our meetings in the sunroom overlooking the bay. We sat around the firepit one night and the next were able to go kayaking and fishing. This is a quiet neighborhood where we could relax. There were plenty of bedding, towels and such for our large group. Everything worked as described.
5.0
We had a great time. The home is sos city’s and comfortable, and the yard and view of the Chesapeake is amazing. The host was so easy to interact with, made for a wonderful experience on every level.
5.0
Our family had such a great time. We caught some crabs and even steamed more. Owner provided stemer and a great contact to buy crabs from. House was very comfortable and was very well stocked. We enjoyed the fire pit and made smores. We would definitely rent this property again.
5.0
This property offered everything. Absolutely great views of the bay, large expansive grassy areas for any type of outdoor games, both patio and deck areas with table and chairs. So peaceful and relaxing. We had a great time!
5.0
We had a large group of extended family together for a long weekend centered around our son’s wedding at a nearby venue. The wide open space, comfortable rooms and grounds filled with entertainment options including cornhole, fishing, kayaking etc, provided the perfect environment for us all to have fun together between the wedding events. The bay and island were beautiful, everything in the house was in perfect shape, and the instructions and information the host provided were so helpful for us to get settled in quickly.
5.0
There was plenty of room to relax inside and outside. Lots of room to eat with a group inside or outside. I loved the outside shower. Watched the dolphins traveling up and down the bay and kayaked. It was great having a second fridge and second oven.
My group had cocktails in the afternoon in the gazebo so we were outside but out of the sun.
I would highly recommend it.
5.0
This place is wonderful, and just what we were looking for. Wonderful views no matter where you looked, and there was even a turkey that took daily walks down the road.
5.0
The house has everything we need. The view is amazing. The host is so kind and easy to communicate. This is our second time, and we will be back again.
5.0
It is very easy to rent the property. The property owner is very cheerful and helpful. It is a beautiful spot and a great area.
5.0
My family had a wonderful relaxing week here, the house was clean and spacious and the view of the bay was outstanding. What can be better to drink your morning coffee and watch the
dolphins? We have been to Gwynn Island three times and it never disappoints .
5.0
Beautiful home
My family and i enjoyed the stay. Beautiful home and beautiful views!
5.0
Family Gathering
We had a wonderful vacation! The house was comfortable and well equipped. There are so many areas to gather and enjoy such as the upper deck, beach, fire pit, gazebo, sunroom, dining room. Each of these areas provided plenty of comfortable seating. The grandchildren loved the sandy beach and they were able to swim safely. The only difficulty we experienced was our timing with a jellyfish bloom. We would highly recommend this property.
5.0
The perfect getaway
Quiet. Peaceful. Beautiful. So many ways to describe this gorgeous property and location. Brian is a wonderful host, always a text away when we needed to reach him. The photos do NOT do the property justice. The rooms are spacious and clean, the kitchen, dining, and living area are bright and open. The sun room was a perfect spot to watch the storms we had on one of our days. We loved being to close to the beach…the morning dolphin shows are incredible. If you’re looking for a relaxing beach vacation, this is your place.
5.0
Gwynn’s
Very nice
5.0
great time in piankatank
The property both inside and out was a pleasant surprise being as good or better then listed. Pleanty of room inside and a lot of outdoor space with a nice beach that everyone enjoyed. Brian the owner provided excellant directions to the house plus directions about almost anything you could think of about the house. When a problem arose (something the owner could not control happening) Brian was easy to contact and took care of it quickly. I would recomend this property to anyone.
5.0
Lovely place
When we walked through the door we couldn't help but smile. It was IMMACULATE, spacious, and very comfortable. It's not REMOTE-remote; groceries and 'civilization' are nearby. The beach is nice and we all -- especially the kids -- had a great time. We had a heck of a storm while we were there; the wind was moving the outdoor furniture on the upper deck from one side of the deck to the other. It's fun to see the fury of the Bay at its wildest (from a safe distance).
5.0
Perfect little getaway
Perfect little getaway, this was our second time visiting the area for an early summer getaway & we adore the town for lunch & ice cream, bringing pizza back for dinner. This home was clean, comfortable & a beautiful spot to relax & enjoy.
5.0
Beautiful house and views on coastal island.
We had a great time. Long weekend visit to gywnn island. Fantastic views,private beach. We definitely come back for a longer stay.
FAQs
How much does this house cost compared to others in Chesapeake Bay?
The average price for a rental in Chesapeake Bay is $379 per night. This rental is $565 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at PRIVATE BEACH on the Chesapeake Bay with 300 feet of shoreline?
We found 10 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, parking, and laundry.
Explore similar vacation rentals in Chesapeake Bay
Explore all rentals in Chesapeake BayStart earning One Key rewards
Very private riverfront, beach, nature for all to enjoy. High Speed Internet!!
House
in Bohannon12 guests · 6 bedrooms · 4 baths
Garden · Pool · Pets allowed
Nestled in Chesapeake Bay, this House is perfect for your next vacation. Enjoy Very private riverfront, beach, nature for all to enjoy. High Speed Internet!!'s top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Beachfront
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
House
in Stevensville26 guests · 5 bedrooms · 4 baths
Garden · Pool · Pets allowed
Looking for a memorable stay in Chesapeake Bay? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.
$$$$
Chesapeake Bay House with Dock & Private Beach
House
in Elkton12 guests · 5 bedrooms · 4 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Looking for a memorable stay in Chesapeake Bay? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.
$$$$
Start earning One Key rewards
THE LIGHTHOUSE INN..Imagine Walking 2 Blocks And Having Your Feet In The Sand!!!
House
in Cape Charles14 guests · 4 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at THE LIGHTHOUSE INN..Imagine Walking 2 Blocks And Having Your Feet In The Sand!!! for $824 for your next trip.
$$$$
Start earning One Key rewards
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
House
in Cambridge15 guests · 4 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette
When traveling to Chesapeake Bay, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $802 per night.
$$$$
Gorgeous Waterfront Estate--Private Pool, Pier, Tennis Court, Firepit
House
in Mathews12 guests · 5 bedrooms · 5 baths
Garden · Pool · Kitchen or Kitchenette
Are you ready to indulge in a relaxing getaway? Our House in Chesapeake Bay has everything you need for a rejuvenating stay. Treat yourself to Gorgeous Waterfront Estate--Private Pool, Pier, Tennis Court, Firepit's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
$$$$
Start earning One Key rewards
Chesapeake Bay Beachfront Retreat
House
in White Stone12 guests · 4 bedrooms · 5 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Nestled in Chesapeake Bay, this House is perfect for your next vacation. Enjoy Chesapeake Bay Beachfront Retreat's top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Beachfront
Beachfront Estate on the Chesapeake Bay, Private Beach & 30-Mile View
House
in Reedville14 guests · 5 bedrooms · 5 baths
Garden · Pets allowed · Kitchen or Kitchenette
Indulge in a peaceful retreat at Beachfront Estate on the Chesapeake Bay, Private Beach & 30-Mile View, our elegant House in Chesapeake Bay. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Gorgeous Annapolis Area Waterfront Home!
House
in Severna Park12 guests · 5 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Experience vacation in Chesapeake Bay with our House, Gorgeous Annapolis Area Waterfront Home!. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
Classically Current | Chesapeake Properties
House
in Cape Charles13 guests · 6 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette
The best choice in Chesapeake Bay for House, for $959 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Waterfront Home & Dock, sleeps 8 Max. Eastern shore, Betterton Chestertown MD.
House
in Worton12 guests · 4 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette
Indulge in a peaceful retreat at Waterfront Home & Dock, sleeps 8 Max. Eastern shore, Betterton Chestertown MD., our elegant House in Chesapeake Bay. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Renovated Gem: Walk to Beach, Historic District Shops, Restaurants, Central Park
House
in Cape Charles12 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Top rated
This inviting House in Chesapeake Bay can fit your needs for many types of vacations, at $1,061 per night.
$$$$
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
House
in Pasadena14 guests · 6 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking to create some memories in Chesapeake Bay? Look no further than our House, Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
House
in Stevensville14 guests · 4 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Indulge in a peaceful retreat at Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill., our elegant House in Chesapeake Bay. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Private Waterfront Family Retreat w/ Pool Pickleball Basketball and Volleyball
Farm Stay
in Taylors Island14 guests · 5 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette
Discover the beauty of Chesapeake Bay with a stay at Private Waterfront Family Retreat w/ Pool Pickleball Basketball and Volleyball , a top rated Farm Stay with amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Beachfront Luxury Home w/ Fabulous Garden & Sunset Views!
House
in Cape Charles14 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Beachfront Luxury Home w/ Fabulous Garden & Sunset Views! for $1,077 for your next trip.
$$$$
Start earning One Key rewards
Sweet Retreat - Close to the beach! Sleeps 12 comfortably
House
in Cape Charles12 guests · 6 bedrooms · 6 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
Discover the beauty of Chesapeake Bay with a stay at Sweet Retreat - Close to the beach! Sleeps 12 comfortably, a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Our Home on the Cove: waterfront, peaceful, wooded, comfy, family friendly
House
in Pasadena15 guests · 7 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette
The best choice in Chesapeake Bay for House, for $844 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Front Row Ocean View! 6 Beds! 5 Decks, 4 Baths! Rec Room, Kayaks! Go Coastal!
House
in Norfolk12 guests · 5 bedrooms · 4 baths
Garden · Pool · Pets allowed
This attractive House in Chesapeake Bay, $1,116 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Family friendly 5 bedroom home within Walking distance To CNU
House
in Newport News17 guests · 6 bedrooms · 4 baths
Garden · Pool · Kitchen or Kitchenette
Experience the best of Chesapeake Bay with this House available for $1,002. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Water Views - Close to Downtown Annapolis
House
in Annapolis12 guests · 5 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette
This attractive House in Chesapeake Bay, $922 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Bay Creek Home Close to Private Beach, Pool & Golf
House
in Cape Charles15 guests · 5 bedrooms · 5 baths
Garden · Pool · Kitchen or Kitchenette
Enjoy the best of Chesapeake Bay in our House, Bay Creek Home Close to Private Beach, Pool & Golf. A stunning property with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Waterfront on Hacks Creek next to Vir-Mar Beach on the Chesapeake Bay
House
in Heathsville16 guests · 6 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette
Nestled in Chesapeake Bay, this House is perfect for your next vacation. Enjoy Waterfront on Hacks Creek next to Vir-Mar Beach on the Chesapeake Bay's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
SUNRISE 2 SUNSET VIEWS! Enjoy our beautiful, spacious home steps from the beach!
House
in Cape Charles15 guests · 6 bedrooms · 5 baths
Pool · Kitchen or Kitchenette · Air conditioner
Looking to create some memories in Chesapeake Bay? Look no further than our House, SUNRISE 2 SUNSET VIEWS! Enjoy our beautiful, spacious home steps from the beach!. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Just One House From The Beach Barefoot Bungalow Offers A Sweet Beach Vacation
House
in Cape Charles12 guests · 5 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Parking
Are you ready to indulge in a relaxing getaway? Our House in Chesapeake Bay has everything you need for a rejuvenating stay. Treat yourself to Just One House From The Beach Barefoot Bungalow Offers A Sweet Beach Vacation's exceptional amenities, such as Air conditioner, Dishwasher and Laundry.
$$$$
Charming Annapolis WaterVIEW Home
House
in Annapolis14 guests · 5 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette
Indulge in a peaceful retreat at Charming Annapolis WaterVIEW Home, our elegant House in Chesapeake Bay. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Start earning One Key rewards
Great home for holidays! Large kitchen, firepit & hot tub, beautiful water views
House
in Lancaster12 guests · 4 bedrooms · 3 baths
Garden · Pool · Pets allowed
Nestled in Chesapeake Bay, this House is perfect for your next vacation. Enjoy Great home for holidays! Large kitchen, firepit & hot tub, beautiful water views's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Waterfront Scotland Beach Retreat w/ Private Beach
House
in Ridge12 guests · 6 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Top rated
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Waterfront Scotland Beach Retreat w/ Private Beach for $1,082 for your next trip.
$$$$
Start earning One Key rewards
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
House
in Stevensville14 guests · 5 bedrooms · 2 baths
Garden · Kitchen or Kitchenette · Air conditioner
This House in Chesapeake Bay, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
Circa 1912 charm. 1 block to beach. Sleeps 12. Equipped recreation room!
House
in Cape Charles12 guests · 5 bedrooms · 7 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
House in Chesapeake Bay, for $940 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
Chesapeake Bay travel inspiration
Read our blogGuides
Best Dining in Myrtle Beach: A Food Lover’s Dream
Guides
Best East Coast Beaches and Getaway Locations You Can’t Miss
Budget Travel
7 Most Affordable Snowbird Destinations for 2025
Guides
Top Activities to Try in Panama City Beach, Florida
Guides
Top Things to Do in Gulf Shores, Alabama: Adventure and Fun Await
Local Culture
Exploring Miami’s Wynwood District: Street Art, Food, and More
Guides
Fun Things to Do in Ocean City, Maryland
Local Culture
A Foodie’s Guide to the Best Dining in Orlando, Florida