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Chesapeake Bay villas
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2157 Villa rentals in Chesapeake Bay

Find the Best Holiday Houses with Swimming Pool in Chesapeake Bay

Dip in whenever you like, as these vacation homes in Chesapeake Bay come with a swimming pool on-site.

Walnuts - Chesapeake Bay
Chesapeake Bay
10/01 – 10/05
$209/nighttotal: $836 (4 )

Walnuts

1 3
house , Garrison
Walnuts is a house located in Owings Mills, 10-13 miles from attractions such as Towson University, the Baltimore Zoo, and the Edgar Allan Poe Museum.
This spacious 17,650 square foot residence accommodates up to 11 guests with 1 bedroom, 1 bathroom, air conditioning, a swimming pool, a garden, and complimentary Wi-Fi.
The Schooner Inn - Chesapeake Bay
8.8 4920 reviews
Chesapeake Bay
08/23 – 08/28
$267/nighttotal: $1335 (5 )

The Schooner Inn

1 2
hotel , Virginia Beach
The Schooner Inn, a two-star Virginia Beach hotel, boasts a beachfront location near the Virginia Beach Boardwalk, offering easy access to shops and restaurants.
This 1-bedroom, 1-bathroom lodging features kitchenettes, private balconies with ocean views, a swimming pool, and limited on-site parking; water sports are readily available nearby.
Hosta Cottage | Creekfront Nature Escape W/ Kayaks, Fire Pit + Resort Access, Pet Friendly - Chesapeake Bay
9.6 5 reviews
Chesapeake Bay
08/29 – 09/05
$251/nighttotal: $1757 (7 )

Hosta Cottage | Creekfront Nature Escape W/ Kayaks, Fire Pit + Resort Access, Pet Friendly

1 2
cottage , Sanford
This waterfront cottage near the Eastern Shore of Virginia is conveniently located within 12 miles of the Virginia Welcome Center at New Church, Bloxom Winery, and the Wallops Flight Facility.
This pet-friendly, one-bedroom, one-bathroom vacation rental sleeps two guests and boasts a fully equipped kitchen, private balcony, swimming pool, and access to outdoor grills; limited housekeeping is available.
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Chesapeake Bay
Chesapeake Bay
10/01 – 10/05
$348/nighttotal: $1392 (4 )

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

4 3
house , Trappe
This spacious vacation home is located in Trappe, just a short drive from the Academy of the Arts and a scenic trip to Federalsburg Marina. The house offers a comfortable stay for large groups or families, with four bedrooms, three bathrooms, and a generous floor area of 2200 square feet. Enjoy the private pool, the shaded gazebo, and the fully equipped kitchen with a dishwasher and oven. Relax in the air-conditioned house with free Wi-Fi access and a flat-screen TV.

Best Chesapeake Bay houses with a kitchen

Cozy Haven In Hampton Roads Near Beaches, Military Bases & Historic Sites - Chesapeake Bay
9.7 9 reviews
Chesapeake Bay
10/01 – 10/05
$174/nighttotal: $696 (4 )

Cozy Haven In Hampton Roads Near Beaches, Military Bases & Historic Sites

3 3
house , Hampton
This Hampton vacation rental is conveniently located near the Virginia Living Museum (11 miles) and Newport News/Williamsburg International Airport (12 miles).
The 110-square-foot home features two bedrooms, one bathroom, and accommodates up to 11 guests, offering free Wi-Fi, parking, and a fully equipped kitchen.
Esva Down By The Sea & Pet Friendly - Chesapeake Bay
9.8 7 reviews
Chesapeake Bay
07/20 – 07/27
$264/nighttotal: $1848 (7 )

Esva Down By The Sea & Pet Friendly

2 4
cottage , Savageville
This seaside cottage rental in Onancock, Virginia, offers easy access to the Onancock Wharf, Kegotank Bay, and is a short drive from Chincoteague Island (30 minutes) and Cape Charles (40 minutes).
This 1000-square-foot vacation home features two bedrooms, one bathroom, accommodates four guests, and includes amenities such as air conditioning, a full kitchen (fridge, microwave), Wi-Fi, and a private garden with parking.
Bay Front Manor House - Chesapeake Bay
9.0 1 review
Chesapeake Bay
08/23 – 08/28
$153/nighttotal: $765 (5 )

Bay Front Manor House

1 2
house , Deale
This Bay Front Manor House in Deale offers convenient access to Annapolis Harbor, 20 miles away, and Washington D.C. attractions, including Nationals Park and the U.S. Capitol, both 30 miles away, with Baltimore - Washington International Airport located 33 miles from the property. This 15,070 square foot manor features one bedroom, one bathroom, and accommodates up to 11 guests with air conditioning, a full kitchen, private parking, and complimentary Wi-Fi, while prohibiting bachelor(ette) parties.
"Gull Cottage" Charming Tiny House On Chesapeake Bay-boat Launch/slip Included - Chesapeake Bay
9.8 68 reviews
Chesapeake Bay
07/20 – 07/27
$184/nighttotal: $1288 (7 )

"Gull Cottage" Charming Tiny House On Chesapeake Bay-boat Launch/slip Included

1 4
cabin , Kilmarnock
This waterfront apartment is situated just a short drive from Kilmarnock, offering stunning views of the Chesapeake Bay and easy access to local attractions. It has earned excellent user ratings, making it a popular choice for travelers. This comfortable rental offers 380 square feet of living space with one bathroom, perfect for a couple or small family. Enjoy access to a private boat ramp, a garden, a spa, and a terrace, along with a full kitchen, air conditioning, and a jacuzzi.

Frequently Asked Questions about villa rentals in Chesapeake Bay

Destinations nearby

Best Chesapeake Bay houses with air conditioning

El  Camino - Chesapeake Bay
10 54 reviews
Chesapeake Bay
08/23 – 08/28
$184/nighttotal: $920 (5 )

El Camino

1 2
cabin , Piney Point
This Piney Point waterfront cottage is located less than a mile from Cardinal Gibbons Park and First District Community Park, and about 3 miles from Saint Inigoes State Forest, offering easy access to outdoor recreation. This one-bedroom, one-bathroom getaway sleeps three guests and features a fully equipped kitchen, Smart TV, barbecue grill, and a terrace with stunning water views.
Bubba Butler's Cottage - Chesapeake Bay
9.8 28 reviews
Chesapeake Bay
07/30 – 08/05
$215/nighttotal: $1290 (6 )

Bubba Butler's Cottage

3 6
cottage , Urbanna
This Locust Hill cottage, near the Middlesex County Museum, Piankatank River Golf Club, and Urbanna Historic District (all within 9 miles), offers easy access to White Stone Beach (11.6 miles away).
This three-bedroom, two-bathroom vacation home sleeps six and includes amenities such as a washer, dryer, and air conditioning, making it perfect for families or groups exploring Urbanna and its surrounding attractions.
Cabin At Holdens Creek On Eastern Shore Of Va - Chesapeake Bay
9.8 187 reviews
Chesapeake Bay
08/29 – 09/05
$127/nighttotal: $889 (7 )

Cabin At Holdens Creek On Eastern Shore Of Va

1 2
cabin , Sanford
This Sanford cabin is located in a peaceful rural setting, just 25 kilometers from attractions like Bloxom Winery, Wallops Flight Facility, and the Eastern Shore Railway Museum. It has received excellent guest ratings and offers a relaxing escape from city life.
This 800-square-foot vacation rental comfortably sleeps 6 guests in one bedroom and one bathroom. Enjoy modern amenities like air conditioning, WiFi, and a fully equipped kitchen, as well as outdoor features like a garden, terrace, and barbecue grills.
The Rene Carr House - Chesapeake Bay
Chesapeake Bay
07/30 – 08/05
$218/nighttotal: $1308 (6 )

The Rene Carr House

1 6
house , Elkton
This Elkton rental property, the Rene Carr House, is conveniently located 7.4 miles from Dayett Station and 8.2 miles from the University of Delaware.
This 1100 square foot residence accommodates up to 11 guests and features a fully equipped kitchen, air conditioning, a garden, and complimentary WiFi and private parking.

Best Chesapeake Bay villas and beach houses with jacuzzi

Waterfront Cambridge Gem W/ Hot Tub, Pool & Dock! - Chesapeake Bay
Chesapeake Bay
10/01 – 10/05
$3975/nighttotal: $15900 (4 )

Waterfront Cambridge Gem W/ Hot Tub, Pool & Dock!

7 3
house , Madison
This waterfront estate is situated in Woolford, Maryland, 27 miles from the Academy of the Arts and 49 miles from Salisbury-Ocean City Wicomico Regional Airport, offering easy access to area attractions.
This 10,330-square-foot luxury home boasts seven bedrooms, six bathrooms, and accommodates up to 53 guests, featuring a private pool, hot tub, bar, and free bicycles for exploring the surrounding area.
Luxury Bed And Breakfast For A Weekend Getaway Near Susquehanna State Park, Maryland - Chesapeake Bay
10 3 reviews
Chesapeake Bay
08/23 – 08/28
$185/nighttotal: $925 (5 )

Luxury Bed And Breakfast For A Weekend Getaway Near Susquehanna State Park, Maryland

1 2
house , Port Deposit
This luxury bed and breakfast suite is located 23 miles from the University of Delaware in Port Deposit, offering a weekend getaway near Susquehanna State Park, Maryland.
This 200 square feet suite accommodates up to 3 guests with 1 bedroom and 1 bathroom, featuring air conditioning, a full kitchen with a dishwasher and microwave, a hot tub, and a private patio.
Historic Row Home 1 Block From Gate 1 At Usna - Chesapeake Bay
9.6 5 reviews
Chesapeake Bay
10/01 – 10/05
$897/nighttotal: $3588 (4 )

Historic Row Home 1 Block From Gate 1 At Usna

3 3
house , Annapolis
This Annapolis row house is located one block from the US Naval Academy's Gate 1, 1.1 miles from Annapolis Harbor, and 30 miles from Baltimore, offering easy access to these landmarks.
This 2000-square-foot property features three bedrooms, three bathrooms, accommodates up to 16 guests, and includes a fully equipped kitchen, free Wi-Fi, air conditioning, a private patio, and a garden.
The Carraige House Of Mount Vernon - Chesapeake Bay
10 2 reviews
Chesapeake Bay
07/20 – 07/27
$315/nighttotal: $2205 (7 )

The Carraige House Of Mount Vernon

3 4
house , Baltimore
The Carriage House is a three-bedroom villa in Baltimore, conveniently located a short walk from Penn Station and the Walters Art Museum, and within a mile and a half of the Inner Harbor and Baltimore Convention Center.
This 1350-square-foot Baltimore house features three bathrooms, sleeps up to 11 guests, and includes amenities such as a fully equipped kitchen, free Wi-Fi, air conditioning, a jacuzzi, and a private balcony.
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