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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.

The Nest On The Shore - Chesapeake Bay
Chesapeake Bay
07/30 – 08/05
$897/nighttotal: $5382 (6 )

The Nest On The Shore

1 6
house , Cape Charles
This vacation home in Cape Charles is a secluded escape located 35 miles from Norfolk International Airport.
This house offers accommodation for 19 guests with 2 bathrooms, a private swimming pool, a terrace, air conditioning, internet, and a fully equipped kitchen.
Waterfront Urbanna Home W/ Private Dock & Pool - Chesapeake Bay
10 10 reviews
Chesapeake Bay
08/29 – 09/05
$452/nighttotal: $3164 (7 )

Waterfront Urbanna Home W/ Private Dock & Pool

3 2
cottage , Urbanna
This Urbanna waterfront home is located 1.6 miles from the Urbanna Historic District and 4.5 miles from the Middlesex County Museum, offering stunning water views and easy access to local attractions.
This 1780-square-foot, six-bedroom, two-bathroom house sleeps six guests and features a private pool, patio with gas grills, fully equipped kitchen with dishwasher, in-unit laundry, and ample parking.
Oceanfront Condo, Ocean View And Indoor Pool - Chesapeake Bay
9.6 5 reviews
Chesapeake Bay
08/23 – 08/28
$624/nighttotal: $3120 (5 )

Oceanfront Condo, Ocean View And Indoor Pool

2 2
house , Virginia Beach
This oceanfront Virginia Beach condo, a 4-minute walk from Croatan Beach, is 1.4 miles from the Virginia Aquarium & Marine Science Center and 1.8 miles from the Virginia Beach Convention Center.
This 1,100-square-foot property features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, a private balcony, access to an indoor pool, and free parking.
Oasis By The Bay - Waterfront Heated Pool Hot Tub - Chesapeake Bay
10 3 reviews
Chesapeake Bay
10/01 – 10/05
$1620/nighttotal: $6480 (4 )

Oasis By The Bay - Waterfront Heated Pool Hot Tub

6 3
house , Highland Beach
This Annapolis waterfront home, located 0.2 miles from Bay Ridge Beach and 4.8 miles from Annapolis Harbor, offers private bay access.
This 5,600-square-foot residence boasts six bedrooms, five bathrooms, sleeps 23 guests, and includes a heated pool, jacuzzi, sauna, spa, and fully equipped kitchen.

Best Chesapeake Bay houses with a kitchen

Loraine's Retreat - Chesapeake Bay
Chesapeake Bay
06/27 – 07/04
$706/nighttotal: $4942 (7 )

Loraine's Retreat

3 3
house , Virginia Beach
Loraine's Retreat, a three-bedroom, two-bathroom Virginia Beach house rental, is conveniently located 1.2 miles from the Virginia Beach Convention Center, 2.8 miles from the Virginia Aquarium & Marine Science Center, and 17 miles from Norfolk International Airport.
This vacation home sleeps 17 guests and boasts a fully equipped kitchen with a fridge and dishwasher, a swimming pool, free Wi-Fi, on-site parking, and proximity to attractions such as the King Neptune Statue and Neptune's Park.
Historic 3-story Fells Point Rowhouse W/ Backyard! - Chesapeake Bay
Chesapeake Bay
06/27 – 07/04
$287/nighttotal: $2009 (7 )

Historic 3-story Fells Point Rowhouse W/ Backyard!

3 3
house , Baltimore
This historic 3-story Fells Point rowhouse is located in Baltimore's Fells Point district, offering proximity to the Pier Six Concert Pavilion (1 mile), the Korean War Memorial (1.1 miles), and the Inner Harbor (1.4 miles).
This pet-friendly house provides 1000 square feet of living space with air conditioning, free Wi-Fi, a fully equipped kitchen, and three bathrooms, accommodating up to 11 guests with a private backyard and outdoor dining area.
Back Creek Villa With Sunroom - Chesapeake Bay
9.9 29 reviews
Chesapeake Bay
08/23 – 08/28
$251/nighttotal: $1255 (5 )

Back Creek Villa With Sunroom

1 2
house , Solomons
This Solomons Island upper duplex unit offers stunning sunrise views of Back Creek and is a short walk from restaurants, ice cream shops, and the Tiki Bar.
The two-bedroom, one-bathroom rental sleeps five, features a kitchen with a fridge, freezer, and microwave, includes air conditioning, parking, internet, and provides pier access with optional slip rental.
3 Mi To Washington College! Updated Home W/ Patio - Chesapeake Bay
Chesapeake Bay
06/27 – 07/04
$229/nighttotal: $1603 (7 )

3 Mi To Washington College! Updated Home W/ Patio

3 3
house , Kingstown
This vacation home in Kingstown is located 48 miles from New Castle Airport.
This 1000 square foot house accommodates up to 7 guests with 3 bedrooms, 1 bathroom, a fully equipped kitchen, air conditioning, and a garden, offering complimentary WiFi and private parking.

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Best Chesapeake Bay houses with air conditioning

Deal Island Bay Cottage - Chesapeake Bay
9.4 319 reviews
Chesapeake Bay
08/23 – 08/28
$187/nighttotal: $935 (5 )

Deal Island Bay Cottage

3 2
cottage , Chance
The Deal Island Bay Cottage is a short walk from a Chesapeake Bay beach with beautiful sunsets, offering a peaceful escape from the hustle and bustle of city life. The cottage boasts excellent ratings for user experience, location, and cleanliness.
This 3-bedroom, 2-bathroom ranch home spans 1550 square feet and comfortably accommodates up to 8 guests. Enjoy modern amenities like high-speed internet, a fully equipped kitchen, central AC, and a screened-in porch, plus activities like kayaking, crabbing, and wildlife viewing.
El  Camino - Chesapeake Bay
10 54 reviews
Chesapeake Bay
06/27 – 07/04
$184/nighttotal: $1288 (7 )

El Camino

1 3
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.
Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc. - Chesapeake Bay
10 51 reviews
Chesapeake Bay
06/27 – 07/04
$316/nighttotal: $2212 (7 )

Relaxing, Peaceful House In Calvert County, Md Close To Beach Towns And Dc.

2 3
cottage , Dunkirk
This charming cottage sits just a short walk from Fridays Creek Winery and a quick drive to the Patuxent River, offering a peaceful escape in a scenic location. It's rated excellent by previous guests, making it a popular choice for travelers seeking a relaxing stay.
The 900 square foot cottage comfortably accommodates up to 4 guests with 2 bedrooms and 1 bathroom. Enjoy the amenities like a private pool, barbecue grills, and a spacious patio, perfect for relaxing and enjoying the beautiful surroundings.
Historic Cottage On Ware River Estate - Chesapeake Bay
10 511 reviews
Chesapeake Bay
08/29 – 09/05
$193/nighttotal: $1351 (7 )

Historic Cottage On Ware River Estate

1 2
cottage , Gloucester Courthouse
This charming cottage sits on a river, just 5.4 miles from Riverside Walter Reed Hospital and 12 miles from Machicomoco State Park. It's a great option for those looking to explore Gloucester Courthouse and its surrounding area. Guests consistently rate this rental as excellent for its location, cleanliness, and overall experience.
The one-bedroom cottage comfortably sleeps up to four guests and features a fully equipped kitchen, a spa tub, a fireplace, and a patio. Enjoy outdoor activities like grilling, relaxing in the garden, or taking advantage of the riverfront location for fishing or kayaking.

Best Chesapeake Bay villas and beach houses with jacuzzi

Dragonfly Cove - Chesapeake Bay
Chesapeake Bay
10/01 – 10/05
$677/nighttotal: $2708 (4 )

Dragonfly Cove

1 3
house , Tilghman Island
This house on Tilghman Island is located 16 miles from the Academy of the Arts in Mount Pleasant and 66 miles from Baltimore-Washington International Airport.
This property offers air conditioning, a private swimming pool, a hot tub, and a fully equipped kitchen for up to 7 guests, with free high-speed Wi-Fi and private parking.
Second Floor East Standard Deluxe - Chesapeake Bay
Chesapeake Bay
08/29 – 09/05
$479/nighttotal: $3353 (7 )

Second Floor East Standard Deluxe

1 2
house , Charlestown
This Charlestown vacation home, located 30 miles from the Old Dutch House in northeastern Delaware, also offers easy access to the University of Delaware and Dayett Station, both within 21 miles.
The one-bedroom, one-bathroom house sleeps nine guests and boasts a fully equipped kitchen, private parking, a swimming pool, jacuzzi, fitness center, tennis court, and free Wi-Fi; nearby activities include a children's playground and laundry service.
Adorable Beach Cottage W/ Hot Tub & Tropical Bar! - Chesapeake Bay
9.1 29 reviews
Chesapeake Bay
08/23 – 08/28
$307/nighttotal: $1535 (5 )

Adorable Beach Cottage W/ Hot Tub & Tropical Bar!

2 2
house , Chesapeake Beach
This Chesapeake Beach cottage is a popular choice for families and pet owners due to its spacious floor plan, outdoor amenities, and convenient location near the beach and attractions. It has received very good user and location ratings, and an excellent cleanliness rating.
The cottage features two bedrooms, one bathroom, and a sofa bed, accommodating up to six guests in 960 square feet of space. It includes a fully equipped kitchen, a private deck for grilling and outdoor relaxation, and access to a community pool. Guests can also enjoy the cottage's jacuzzi, terrace, garden, and barbecue grills.
Cottage On The Bay - Chesapeake Bay
8.8 3 reviews
Chesapeake Bay
08/23 – 08/28
$247/nighttotal: $1235 (5 )

Cottage On The Bay

2 2
cottage , Long Beach
This St. Leonard beach house offers proximity to three private beaches within walking distance or a short drive, and is 15 miles from Solomons Island and Prince Frederick.
This family-friendly cottage accommodates four guests with two bedrooms and one bathroom, featuring a full kitchen, air conditioning, a jacuzzi, a garden, parking, and shared amenities like a fire pit and kayaks.
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