Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths
5.0
Outstanding(71 Reviews)House in Chesapeake Bay, NC
9 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
Great for petsBring all your friends and family, even the furry ones
About this house rental
Holly Knoll is the perfect Saturday to Saturday getaway for families.
This stunningly beautiful, private and secluded waterfront home is yours to enjoy. Swimming pool, hot tub, dock, canoe, and kayaks allow you to enjoy this wonderful oasis on your own terms. The home is an open concept floor plan with the gourmet kitchen, living and dining room surrounded by floor to ceiling windows to allow in the natural beauty.
The swimming pool and lounge area provide hours of fun and relaxation. (The pool is heated throughout the season between 78-82 degrees) The pool was built with entertaining in mind. Surrounded by gardens and nature and truly maximizing the views of the St. Mary's you will find this oasis a much enjoyed retreat. The hot tub is on offer and requires an additional fee for activation. The pool and spa are completely automated and are attended to weekly by a professional service team. A gas grill, large seating areas and comfortable furniture complete the package.
Announcing additional accommodations for the 2023 Season.
The Boat Loft is ideal for guests who would like to have grand parents or another couple join the party (two person occupancy maximum) yet have their own self-contained accommodation. The Loft affords guests more privacy and a space to unwind away from the activity. The Boat Loft is attached to the main house and has its own secure entry. Well appointed, the Loft is a studio space full of light bringing nature into focus. A comfortable King bed, seating area for four, walk in shower and complete kitchen provide all of the comforts.
The Boat Loft is available only to guests booking Holly Knoll during the rental season and for an additional fee. The CLUB FEE will already be included in the quote. If you do not need the Boat Loft, just let me know and I will remove the CLUB FEE from Quote prior to booking or refund from the bill.
Holly Knoll is situated one mile from Historic St. Mary’s City and St. Mary’s College, Holly Knoll is a world apart from the everyday. Unwind and collect those precious memories with family and friends. Crab from the dock and enjoy Maryland’s finest shellfish. Take the Canoe or Kayak and explore the surrounding tidal estuary and small ponds. Soak in the sun and quiet beauty and experience old-fashioned tidewater summers. The St Mary's River is one of the cleanest waterways feeding the Chesapeake and the property is part of the Maryland Oyster Restoration Program.
Let your inner Julia escape the confines of the everyday. The gourmet kitchen has every amenity a budding chef could want. Dual fuel Wolf range with two ovens and Cuisinart as well as top of the line All Clad cookware will assist you as you prepare fresh produce gathered from the local farmers market and Amish farms.
Holly Knoll was built in 1993 and was named from the large grove of American Holly that grows along the river and stream banks. It was situated to be in harmony with the natural environment and to take advantage of the beauty of the St. Mary’s River.
Holly Knoll's main house consists of four nicely appointed bedrooms over two floors, accommodating 6-7 guests comfortably. Tucked away on the first floor is the Master Suite complete with steam shower. A full bath is also located on the first floor. The remaining three guest rooms occupy the second floor and share a bath. The second floor bedrooms consist of a king, a king, and a full bed. So in total, the main house has 3 king beds and 1 full bed. With the Boat Loft Holly Knoll has 4 king beds and 1 full bed.
There is a separate office located on the first floor should you choose to connect to the office. High Speed Internet delivers!
One mile from historic St. Mary's City, Maryland's original capital, and 15 miles from beautiful Pt. Lookout Park, Holly Knoll is well located for you to enjoy the beauty and bounty of the Chesapeake Bay. Day trips to Solomon's Island, Smith Island, Leonardtown or Loveville will satisfy your inner adventurer. Visit great little cafes, Amish markets and antique shops and experience for yourself how quiet, serene and hospitable life can be just a short 1.5 hour drive south of Washington DC.
Come and relax, unwind and re-boot! Well behaved dogs (2 max) will be considered.
Call or Text for additional information.
This stunningly beautiful, private and secluded waterfront home is yours to enjoy. Swimming pool, hot tub, dock, canoe, and kayaks allow you to enjoy this wonderful oasis on your own terms. The home is an open concept floor plan with the gourmet kitchen, living and dining room surrounded by floor to ceiling windows to allow in the natural beauty.
The swimming pool and lounge area provide hours of fun and relaxation. (The pool is heated throughout the season between 78-82 degrees) The pool was built with entertaining in mind. Surrounded by gardens and nature and truly maximizing the views of the St. Mary's you will find this oasis a much enjoyed retreat. The hot tub is on offer and requires an additional fee for activation. The pool and spa are completely automated and are attended to weekly by a professional service team. A gas grill, large seating areas and comfortable furniture complete the package.
Announcing additional accommodations for the 2023 Season.
The Boat Loft is ideal for guests who would like to have grand parents or another couple join the party (two person occupancy maximum) yet have their own self-contained accommodation. The Loft affords guests more privacy and a space to unwind away from the activity. The Boat Loft is attached to the main house and has its own secure entry. Well appointed, the Loft is a studio space full of light bringing nature into focus. A comfortable King bed, seating area for four, walk in shower and complete kitchen provide all of the comforts.
The Boat Loft is available only to guests booking Holly Knoll during the rental season and for an additional fee. The CLUB FEE will already be included in the quote. If you do not need the Boat Loft, just let me know and I will remove the CLUB FEE from Quote prior to booking or refund from the bill.
Holly Knoll is situated one mile from Historic St. Mary’s City and St. Mary’s College, Holly Knoll is a world apart from the everyday. Unwind and collect those precious memories with family and friends. Crab from the dock and enjoy Maryland’s finest shellfish. Take the Canoe or Kayak and explore the surrounding tidal estuary and small ponds. Soak in the sun and quiet beauty and experience old-fashioned tidewater summers. The St Mary's River is one of the cleanest waterways feeding the Chesapeake and the property is part of the Maryland Oyster Restoration Program.
Let your inner Julia escape the confines of the everyday. The gourmet kitchen has every amenity a budding chef could want. Dual fuel Wolf range with two ovens and Cuisinart as well as top of the line All Clad cookware will assist you as you prepare fresh produce gathered from the local farmers market and Amish farms.
Holly Knoll was built in 1993 and was named from the large grove of American Holly that grows along the river and stream banks. It was situated to be in harmony with the natural environment and to take advantage of the beauty of the St. Mary’s River.
Holly Knoll's main house consists of four nicely appointed bedrooms over two floors, accommodating 6-7 guests comfortably. Tucked away on the first floor is the Master Suite complete with steam shower. A full bath is also located on the first floor. The remaining three guest rooms occupy the second floor and share a bath. The second floor bedrooms consist of a king, a king, and a full bed. So in total, the main house has 3 king beds and 1 full bed. With the Boat Loft Holly Knoll has 4 king beds and 1 full bed.
There is a separate office located on the first floor should you choose to connect to the office. High Speed Internet delivers!
One mile from historic St. Mary's City, Maryland's original capital, and 15 miles from beautiful Pt. Lookout Park, Holly Knoll is well located for you to enjoy the beauty and bounty of the Chesapeake Bay. Day trips to Solomon's Island, Smith Island, Leonardtown or Loveville will satisfy your inner adventurer. Visit great little cafes, Amish markets and antique shops and experience for yourself how quiet, serene and hospitable life can be just a short 1.5 hour drive south of Washington DC.
Come and relax, unwind and re-boot! Well behaved dogs (2 max) will be considered.
Call or Text for additional information.
Amenities
Pool
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
Hot tub or spa
TV
Family friendly
Map of Chesapeake Bay, NC
Reviews
5.0
Outstanding(71 Reviews)5.0
We have been renting properties since our children were adults. This is by far the best property and host that we experienced. The pictures don’t do the property justice. It is so beautiful and such a peaceful area. Jack is a wonderful host and always available should you have any problems. We took our jet skis and for the most part had the whole river to ourselves. I highly recommend this property.
5.0
We celebrated our 40th anniversary this year and decided to take our family on a special vacation to mark the occasion. My husband and I, our three adult children, their spouses, seven-year-old grandchild, and one small pup had a great time at Holly Knoll. We rented the house and the boat loft. There was plenty of room for everyone to gather together, but also spaces to go to get away from it all. The pool was a favorite spot! The dock was a great place to sit and enjoy the sunsets. Everything was very clean, and the kitchen was stocked with everything you could need. Jack, the host, was very responsive. We had a great week!
5.0
Our vacation was wonderful. The house is perfect for us, our adult children, and our grandchildren. Our grandchildren loved being in the pool. The property is beautiful. The beds are very comfortable. The rooms are spacious. We were sad to leave. Thank you to the hosts for sharing their beautiful home.
5.0
Absolutely beautiful property. A couple hiccups along the way with the pool/spa but Jack the host was very responsive and accommodating.
5.0
Wonderful place to spend a week with family. Beautiful pool and hot tub and knock-out, gorgeous view from yard and dock. Fenced Yard is dog friendly which is such a plus and house has literally everything you could need. The River is full of wildlife and beautiful sunsets. Already booked next year!
5.0
Such an amazing property! Property owner is prompt to respond. The house is exceptionally clean. The view of the river is gorgeous. We spent most of our time at the pool, on the dock, and kayaking. Plenty of great restaurants nearby(owner gave great suggestions).
Will book again
5.0
This was our second visit to Holly Knoll. It is very pleasant and peaceful, with well maintained grounds {with pool) on greater Chesapeak bay and a large comfortable house. Even though the host does not live nearby, he was always available and responsive. We are hoping to have our entire family there next year,
As an aside, since there is no other way to give feedback to VRBO, I wish that they would not require entries for which I had no basis for opinion (in this case, "accuracy of listing"0
5.0
Family vacation close to home. Lovely property. Plenty of fun.
5.0
As return guests, we can confidently say that Holly Knoll keeps getting better! Our previous stays were incredible, but this time was even more special. One of the most impressive updates was how skillfully Jack opened up the waterfront view without removing too many trees. This thoughtful approach not only preserved the natural beauty of the surroundings but also enhanced our experience with breathtaking views of the water.
Jack’s attention to detail and dedication to maintaining the property’s charm is evident. The interior was as cozy and inviting as we remembered, and the addition of new amenities (including the larger TV and additional seating) added to the overall comfort of our stay.
The salt water pool and private dock continued to be a highlight of our vacation, providing a perfect oasis for relaxation and fun.
Once again, Jack’s hospitality was second to none. He was always available to ensure we had everything we needed and went above and beyond to make our stay exceptional.
Holly Knoll has become our go-to retreat, and we can’t wait to be back again next year! Thank you, Jack, for making our time at Holly Knoll so memorable.
5.0
4th annual visit to this little bit of paradise, So much to do, or just lie by the pool and relax. The one evening lightning storm was spectacular. Great family retreat!
5.0
What a wonderful place to stay. The house was very spacious and comfortable with lots of little touches like games, flashlights, stuff for a fire. The kitchen was superb, and we made great meal. The outside was amazing! From the family room you could see the garden and St Mary's River with pier. As a gardener, I loved the landscaping. The pool and hut tub really made it a paradise. Even with the rainy weather, we managed to use the pool except for one day. The dogs loved the fenced in yard. Our family loved it and hope to rent again next year.
5.0
This home has everything we needed to enjoy the week in St. Mary’s County. The owner communicated very well, answering our questions and offering suggestions for things to do. I would highly recommend this home for a relaxing time away from the daily grind!
5.0
Beautiful location on the St Mary’s River. Excellent house, extensive amenities, great pool and spa. Owner extremely attentive. I would highly recommend this property.
5.0
Wonderful vacation at this beautiful house!
5.0
The home is clean, spacious and well stocked.
We spent some time sight seeing in the area but always left room in each day to enjoy the spa, pool, yard and dock. Like many others before us, being surrounded by nature, enjoying the amazing view and just spending time together relaxing in the yard, pool, spa were the highlight of our trip! Highly recommend!
5.0
The house is so warm and welcoming we really could not think of anything more that they could have provided.
The pool was beautiful, we couldn’t keep our daughter out of it or the sauna. Our son and his wife fished off the dock and kayaked the days away. Close to other activities and yet feel like you are in your own paradise.
Loved it
5.0
This was our third summer to visit. Wonderful! Each year we make new family memories. Already planning year four. Wonderful host, too.
5.0
Amazing views, gorgeous home. Jack was accessible and communicated quickly.
The pool was where we spent 6 hours a day. Went to dock caught my grandsons first fish, crabs. Saw 2 bald eagles… already booked for next year(that says it all!)
5.0
Located on the St. Mary's river, with a dock and a swimming pool, as well as well landscaped grounds offering privacy, the house is both comfortable and attractive. The kitchen is well equipped, there are 2 bedrooms with king-size beds, another 2 bedrooms in the house plus a 1 bedroom boathouse loft paid for separately. We relaxed and appreciated everything on offer except the new owners didn't know canoe paddles were needed--that will be remedied next year. The host Jack is very cordial and wants to please, helpful. We much appreciated his efforts and willingness to refund when some of our family could not attend at the last minute...We recommend this highly.
5.0
We had an amazing week relaxing by the pool, fishing and just hanging with the family. Holly knoll is a true nature lover’s retreat. We saw turtles, frogs, hummingbirds and tons of butterflies while enjoying the yard.
We picked up fresh eggs and meat from the local farm, went to Solomons Island for great crab cake dinner at the Island Hideaway and shopped at the farmers market on Wednesday. Thanks Jack for a wonderful stay!
5.0
Relaxing week at Holly Knoll.
We had an amazing week relaxing by the pool, fishing and just hanging with the family. Holly knoll is a true nature lover’s retreat. We saw turtles, frogs, hummingbirds and tons of butterflies while enjoying the yard.
We picked up fresh eggs and meat from the local farm, went to Solomons Island for great crab cake dinner at the Island Hideaway and shopped at the farmers market on Wednesday. Thanks Jack for a wonderful stay!
5.0
Wonderful Stay
This was our 3rd stay, first with the new owner Jack who was very responsive and accommodating. It was also our first stay including the boat house. We were 6 adults with dogs. Go and enjoy you won't regret.
5.0
Comfortable and Relaxing!
We just returned from two weeks at Holly Knoll. It was a great two weeks away! The house is super clean. The pool area is fantastic. We loved going down to the dock to just take in the views of the river. The kitchen really is fully stocked with equipment for your cooking needs! Jack is super responsive and helpful!
5.0
We had a fabulous two-week vacation at Holly Knoll! This is our second year and we have already booked for next summer. Gorgeous waterfront house and grounds with stunning views of St. Marys River (We had coffee each morning on the dock.) Jack is extremely responsive, friendly and accommodating. Could not ask for a better host! The house and grounds are immaculate.
The property is secluded and private yet only a few miles from stores and local attractions. We highly recommend taking advantage of events happening at St. Mary’s College! We attended the outdoor jazz concert one day and the Beer Fest another day. St. Mary’s City and College has much history.
Holly Knoll is an oasis. A dream vacation spot.
5.0
Exceptional
We had a fabulous two-week vacation at Holly Knoll! This is our second year and we have already booked for next summer. Gorgeous waterfront house and grounds with stunning views of St. Marys River (We had coffee each morning on the dock.) Jack is extremely responsive, friendly and accommodating. Could not ask for a better host! The house and grounds are immaculate.
The property is secluded and private yet only a few miles from stores and local attractions. We highly recommend taking advantage of events happening at St. Mary’s College! We attended the outdoor jazz concert one day and the Beer Fest another day. St. Mary’s City and College has much history.
Holly Knoll is an oasis. A dream vacation spot.
5.0
Holly Knoll Getaway on scenic St. Mary's River Maryland
Holly Knoll has everything you need for great vacation: private waterfront home on the St. Mary’s River near historic St. Mary’s City; gourmet kitchen; salt-water pool and hot tub; dock; kayaks and canoe; and great crabbing and fishing. We’ve rented the property the last four years and plan to rent again next year.
5.0
Another Great Visit
This is our second stay this year at Holly Knoll. Larry is a fast and easy communicator responding to any question and quick with a solution. This stay included our sister and again our dog. We were all comfortable there. The setting is very relaxing which is exactly what we needed. As long as you dont book the week we want next year, come and enjoy!
5.0
The week my family and I had at Holly Knoll was wonderful! It was extremely relaxing with most every day by the pool. The views of the bay were excellent from the house and pool. The dock provided peaceful mornings and beautiful sunsets. Crabbing off the dock was a cinch and Larry's suggestion of chicken thighs for bait was spot on. My kids loved pulling up the traps and watching me get pinched by the crabs :). Larry was a very attentive host answering our questions without delay. Enso's, while a small college bakery, provided one of the best biscuits I recall ever having and the buttermilk white bread was a hit! We really enjoyed the stay and would consider Holly Knoll for a future visit.
5.0
Excellent family vacation
The week my family and I had at Holly Knoll was wonderful! It was extremely relaxing with most every day by the pool. The views of the bay were excellent from the house and pool. The dock provided peaceful mornings and beautiful sunsets. Crabbing off the dock was a cinch and Larry's suggestion of chicken thighs for bait was spot on. My kids loved pulling up the traps and watching me get pinched by the crabs :). Larry was a very attentive host answering our questions without delay. Enso's, while a small college bakery, provided one of the best biscuits I recall ever having and the buttermilk white bread was a hit! We really enjoyed the stay and would consider Holly Knoll for a future visit.
5.0
Great trip!
We had the best time at Holly Knoll! The property and house are both beautiful and the host, Larry, is super nice, responsive and easy to get in contact with! Our kids (and dog!) had the best time ever and keep asking when we can go back! We highly recommend it to any family!
5.0
Lovely views with spa, swimming, crabbing, kayaking, and fire pit.
We enjoyed our time so much! Thanks for sharing your comfy home!
5.0
Beautiful views and relaxing week!
Lovely views with spa, swimming, crabbing, kayaking, and fire pit.
We enjoyed our time so much! Thanks for sharing your comfy home!
5.0
Millionaire-dollar view, immaculate pool, great kayaking/crabbing
Holly Knoll offers a wonderful waterfront getaway on a calm cove of the St. Mary's River. We divided our time between kayaking on the river, cooling off in the pool, and mellowing out in the spa. The house is located in the midst of woodland. Herons and osprey fly along the edge of the property. Toads croak at poolside during the evening.
The kitchen is exceptionally well stocked with high-end equipment. A chef would feel at home.
The bedrooms are comfortable, and the bathrooms up to date and clean. The living room/family room is a great place to play games or recline in chairs to read or look outdoors.
Our favorite spot was the patio, where we could sit under an umbrella, gazing over the pool and spa at the play of light on the river. Our favorite activities were kayaking and netting crabs. We caught 23 over six days and had wonderful crab cakes on the seventh.
Larry was a gracious and responsive host.
5.0
Absolutely spectacular spot with something for everyone - swimming, kayaking, crabbing, watching sunsets from the dock, walking distance to St. Mary’s College and City, great kitchen for cooks, and a great Saturday farmer’s market. Larry, the host, is immediately responsive to any question too!
5.0
An oasis in dappled shade
Absolutely spectacular spot with something for everyone - swimming, kayaking, crabbing, watching sunsets from the dock, walking distance to St. Mary’s College and City, great kitchen for cooks, and a great Saturday farmer’s market. Larry, the host, is immediately responsive to any question too!
5.0
Perfection
My family and I spent an incredible week at Holly Knoll. As beautiful as the pictures are, they do not do it justice. Everything exceeded our expectations and Larry could not have been a more pleasant and helpful host. We have already booked another two week stay next year and are already counting down the days! The house, grounds and pool were immaculate upon arrival and Larry was available to answer any questions we had. This was by far the best vacation experience our family has ever had. I highly recommend taking advantage of the crab pots. We caught 36 crabs and had a delicious feast! It is a perfect getaway for people of all ages.
5.0
Second Stay in Paradise
Our first visit, June 2020, was fabulous, so our family of six (oldest son, daughter-in-law, 71/2 yo grandson, nearly 11yo grandson, youngest son & grandmother) eagerly anticipated this year’s (June 2021) visit. We were not disappointed.
The Holly Knoll write-up is not an exaggeration. Larry is a perfect host who has created a peaceful, exquisite woodland retreat. The beautiful home with amenities of spa & pool, river dock, kayaks and canoe have something for everyone in the family to enjoy. And enjoy, we did!
My nearly 11yo grandson learned to kayak this year. The smile on his face is unforgettable. Memories made here are so precious to me as a senior, and I know will be treasured memories for my family throughout their lives, too.
Of course, we’ll be back in 2022!
5.0
Wooded waterfront
If you’re looking for the best of wooded waterfront properties this place is for you. Sunset on the dock was beautiful. The hot tub and pool were my favorites. Even cooking was a pleasure in the chef’s kitchen.
5.0
Having visited Holly Knoll this past October could not wait to pay a repeat visit - and this time in the late spring/early summer to take real advantage of the River and the pool. The week was again simply glorious. The house and the grounds were perfect for a gathering of friends and dogs. Cannot wait to visit again.
5.0
Second stay at Holly Knoll
Having visited Holly Knoll this past October could not wait to pay a repeat visit - and this time in the late spring/early summer to take real advantage of the River and the pool. The week was again simply glorious. The house and the grounds were perfect for a gathering of friends and dogs. Cannot wait to visit again.
FAQs
How much does this house cost compared to others in Chesapeake Bay?
The average price for a rental in Chesapeake Bay is £212 per night. This rental is £564 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths. 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 Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths. Enjoy the water!
Is Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths pet friendly?
Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Waterfront Paradise with Pool & Hot Tub plus 4 King Beds & 4 Full baths?
We found 13 amenities for this rental. This includes pool, air conditioner, pets allowed, kitchen or kitchenette, and internet / wifi.
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!
££££
Spotting Chessie
House
in Maryland10 guests · 5 bedrooms · 4 baths
Pool · Pets allowed · Family friendly
Indulge in a peaceful retreat at Spotting Chessie, our elegant House in Chesapeake Bay. Enjoy amenities including Family friendly, Pool and Pets allowed, and more.
££££
Modern St. Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks & More
House
in Easton10 guests · 5 bedrooms · 4 baths
Garden · Pool · Pets allowed
Looking for a House in Chesapeake Bay, this House for £656 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
££££
Start earning One Key rewards
Blue Heaven - A Dog Friendly North End Beach Cottage - Private Walk to Beach!
Cottage
in Virginia Beach9 guests · 3 bedrooms · 4 baths
Pool · Pets allowed · Kitchen or Kitchenette
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Blue Heaven - A Dog Friendly North End Beach Cottage - Private Walk to Beach! for £623 for your next trip.
££££
Start earning One Key rewards
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
Cottage
in Cambridge9 guests · 4 bedrooms · 2 baths
Garden · Pool · Pets allowed
This Cottage in Chesapeake Bay, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
££££
Start earning One Key rewards
Historic Oxford Waterfront Estate
House
in Oxford12 guests · 7 bedrooms · 6 baths
Garden · Pool · 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 £837 per night.
££££
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.
££££
Chesapeake Bay View
House
in Cape Charles14 guests · 6 bedrooms · 5 baths
Garden · Kitchen or Kitchenette · Air conditioner
Indulge in a peaceful retreat at Chesapeake Bay View, our elegant House in Chesapeake Bay. Enjoy 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.
££££
Private 2 Acre Waterfront Family Retreat with Pool & Pier
House
in Cambridge22 guests · 8 bedrooms · 7 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 Internet / Wifi, and more during your stay.
££££
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 £868. 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, £674 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 £623 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.
££££
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 £739 for your next trip.
££££
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 £662 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
££££
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 £713 per night for your next great vacation.
££££
Beachfront
Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D
House
in Annapolis10 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
This inviting House in Chesapeake Bay can fit your needs for many types of vacations, at £637 per night.
££££
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.
££££
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 £813 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 £686 in Chesapeake Bay, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)
££££
Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!
House
in Annapolis12 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking to create some memories in Chesapeake Bay? Look no further than our House, Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
££££
Sunset Lodge on the Bay
House
in Rock Hall14 guests · 6 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Chesapeake Bay, at £891 per night for your next great vacation.
££££
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.
££££
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 £648. This property is equipped with amenities including Air conditioner, Dishwasher and Fireplace, and more.
££££
Chesapeake Bay travel inspiration
Read our blogGuides
Top Things to Do in Oahu and Honolulu
Guides
Top Things to Do in Fort Lauderdale, Florida
Guides
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