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2157 Villa rentals in Chesapeake Bay
9.8 130 reviews
Chesapeake Bay
06/27 – 07/04
$315/nighttotal: $2205 (7 )
Patuxent River View
2 3
house , Dunkirk
This Dunkirk guest house, near North Beach, Maryland, offers easy access to Herrington Harbor, Herrington on the Bay, and Chesapeake Beach, all within an hour's drive of Washington, D.C., Annapolis, and Baltimore. This newly renovated 900-square-foot home features two bedrooms, one bathroom, and a fully equipped kitchen, accommodating up to four guests and including a swimming pool and Wi-Fi.
10 2 reviews
Chesapeake Bay
06/27 – 07/04
$408/nighttotal: $2856 (7 )
Historic Row Home In Downtown Annapolis
2 3
house , Annapolis
This historic row house in Annapolis's Downtown district is 1.1 miles from Annapolis Harbor and 30 miles from Baltimore's Inner Harbor and Camden Yards. The 1,100-square-foot property features two bedrooms, two bathrooms, accommodates up to 10 guests, and includes a fully equipped kitchen, private patio, garden, free Wi-Fi, and in-unit laundry.
Chesapeake Bay
06/27 – 07/04
$242/nighttotal: $1694 (7 )
Charming 1-bedroom Cottage With Ac In Cozy Harwood
1 3
cottage , Riva
This Anne Arundel County cottage is a short drive from Annapolis and Washington, D.C., offering easy access to regional attractions and is located 6 miles from South River Golf Links. This rental sleeps four guests with one bedroom, a double bed, and a sofa bed, and includes air conditioning and internet for a comfortable stay.
10 3 reviews
Chesapeake Bay
08/29 – 09/05
$185/nighttotal: $1295 (7 )
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.
9.7 7 reviews
Chesapeake Bay
08/29 – 09/05
$211/nighttotal: $1477 (7 )
New, Chic River Bungalow In Historic District
1 2
bungalow , Cambridge
This Cambridge, England bungalow, a renovated former flower shop, is located one block from the River Cam and a five-minute walk from Cambridge's revitalized city center, offering easy access to shops, galleries, and restaurants. This two-bedroom, two-bathroom house sleeps four guests and features a fully equipped kitchen with stainless steel appliances, a dedicated workspace, and a private garden; a fitness center and parking are also available.
10 1 review
Chesapeake Bay
06/27 – 07/04
$262/nighttotal: $1834 (7 )
Peaceful Spacious Lake House Cabin
3 3
cabin , Chesapeake Ranch Estates
This rustic log lodge is located directly on the Chesapeake Bay in Southern Maryland, offering waterfront access and proximity to community private beaches for kayaking, paddleboarding, and fishing, with hiking trails, historic sites in Lusby and Solomons Island, and local restaurants, vineyards, and festivals nearby. This lodge accommodates up to 8 guests and features a gourmet kitchen, air conditioning, Wi-Fi, a garden, parking, two bathrooms, a fire table, and a grill on the back patio with water views, situated approximately 1.5 hours from Washington D.C. and Baltimore.
10 53 reviews
Chesapeake Bay
10/01 – 10/05
$234/nighttotal: $936 (4 )
Charming Waterfront Farmhouse 10 Minutes From Blackwater Nwr - Pet Friendly
2 3
farm , Chesapeake Ranch Estates
This waterfront gîte is located in Fishing Creek, just 5.5 miles from Middle Hooper Island. It has been awarded an excellent user rating and is a popular choice for families visiting Chesapeake Ranch Estates. The gîte has a floor area of 1250 square feet and can accommodate up to 6 guests in its 2 bedrooms and 1 bathroom. It features a fully equipped kitchen, a living room, and a bathroom. Guests can also enjoy the garden, terrace, and barbecue grills. The gîte is also pet-friendly and offers amenities such as air conditioning, internet, and parking.
8.0 9 reviews
Chesapeake Bay
10/01 – 10/05
$77/nighttotal: $308 (4 )
Virginia Vacation Duplex House 1
1 3
house , Virginia Beach
This duplex house is located in Virginia Beach, just a short drive from popular attractions like Mount Trashmore Park, Topgolf Virginia Beach, and Cape Henry Lighthouse. Guests have consistently rated the house highly for its location, cleanliness, and overall experience. The house offers multiple units, providing ample space for families or groups of friends. Enjoy the convenience of free Wi-Fi and private parking, a fully equipped kitchen in some units, and a peaceful setting for relaxation and privacy.
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.
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.
10 4 reviews
Chesapeake Bay
08/23 – 08/28
$139/nighttotal: $695 (5 )
Our Haven Cabin
1 2
cabin , Secretary
This East New Market vacation home is located 21 miles from the Academy of the Arts and 30 miles from Salisbury Zoo. This 900-square-foot, one-bedroom house accommodates up to three guests and features a kitchenette, air conditioning, free Wi-Fi, and private parking, with water sports and fishing available nearby.
Chesapeake Bay
06/27 – 07/04
$408/nighttotal: $2856 (7 )
A Place In The Sun
2 3
house , Virginia Beach
A Place In The Sun is a two-bedroom, two-bathroom Virginia Beach house conveniently located 1.3 miles from the Virginia Beach Convention Center, near the Virginia Aquarium & Marine Science Center and the Virginia Beach boardwalk. This vacation rental sleeps 11 guests and offers free WiFi, on-site parking, a fully equipped kitchen with a fridge, microwave, and dishwasher, and is just 17 miles from Norfolk International Airport.
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.
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.
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.
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.
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
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.
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.
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.
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.
Frequently Asked Questions about villa rentals in Chesapeake Bay
What are the best activities in Baie de Chesapeake?
There's so much to do! You can go crabbing or fishing, rent a boat and explore the islands, or take a scenic drive along the bay. If you like history, there are plenty of historic sites to visit. And of course, you can't forget about the food! There are some amazing seafood restaurants in the area.
What are the best villa rentals in Chesapeake Bay?
What are the advantages of renting a house or a villa in Baie de Chesapeake
Renting a house or villa gives you more space and privacy than a hotel. You can also cook your own meals, which can save you money. And, of course, you'll have access to all the amenities of a home, like a washer and dryer, a full kitchen, and a backyard.
What are the best villa rentals with a pool in Chesapeake Bay?
What exclusive experiences are available when visiting Baie de Chesapeake?
You can go on a private sailing tour of the bay, or take a helicopter ride over the Chesapeake Bay Bridge. You can also book a private chef to come and cook a meal for you in your rental house. And, of course, there are plenty of opportunities to go fishing and crabbing.
What are the best villa rentals with a jacuzzi in Chesapeake Bay?
Which part of Baie de Chesapeake would be ideal for a villa rental?
The Eastern Shore is a great place to rent a villa. It's a beautiful area with lots of beaches, small towns, and historic sites. The area around St. Michaels is especially popular for villa rentals.
What are the best villa rentals for families and kids in Chesapeake Bay?
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.
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.
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.
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
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.
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.
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.
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.