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2157 Villa rentals in Chesapeake Bay
10 79 reviews
Chesapeake Bay
08/29 – 09/05
$179/nighttotal: $1253 (7 )
Idle Hour, A Tranquil 3 Bedroom 1.5 Bath Cottage With Dock & Golf Cart Rental
3 2
cottage , Smith Island
This waterfront cottage on Terrapin Sand Point is only 0.1 miles from the point and 2.5 miles from Smith Island. It is highly rated for its location, cleanliness, and user experience. The cottage has 3 bedrooms and can accommodate up to 6 guests. It features a kitchen with a refrigerator, oven, stovetop, and microwave, as well as free WiFi, air conditioning, and a terrace or balcony. Guests can also enjoy the barbecue grills and garden.
9.1 29 reviews
Chesapeake Bay
07/30 – 08/05
$298/nighttotal: $1788 (6 )
Adorable Beach Cottage W/ Hot Tub & Tropical Bar!
2 6
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.
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.
8.8 5 reviews
Chesapeake Bay
07/20 – 07/27
$212/nighttotal: $1484 (7 )
1 Bedroom Cottage Suite Village In King's Creek Weekly Booking 8days/7nights.
1 4
cottage , Williamsburg
This Williamsburg vacation home is conveniently located 1.6 miles from Colonial National Historical Park and within 6 miles of Busch Gardens Williamsburg and Water Country USA. This 430-square-foot cottage features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen, fireplace, jetted tub, private balcony, two swimming pools (indoor and outdoor), barbecue grills, and a washer/dryer.
9.2 7 reviews
Chesapeake Bay
07/20 – 07/27
$129/nighttotal: $903 (7 )
Charming 1br Cottage W/ Wifi, Ac In Wonderful Wye Mills
2 4
cottage , Queenstown
This Queenstown, Maryland cottage is conveniently located near the Avalon Theatre and The Third Haven Friends Meeting House, offering easy access to area attractions like the Hazel Miner Monument and Adkins Arboretum. This two-bedroom, one-bathroom house sleeps four guests and features a fully equipped kitchen (fridge, microwave), air conditioning, Wi-Fi, a terrace, garden, parking, and a washer/dryer; pets are welcome.
9.6 4 reviews
Chesapeake Bay
10/01 – 10/05
$208/nighttotal: $832 (4 )
Near Chincoteague & Assateague Island\ncharming 2-bedroom Cottage
2 3
cottage , Saxis
This Saxis, Virginia cottage is conveniently located near Bloxom Winery and Somers Cove Marina, offering easy access to the Chesapeake Forest – Dunn Swamp Complex and Kegotank Bay. The two-bedroom, one-bathroom home sleeps four guests comfortably, featuring a queen and a full bed, WiFi, a washer, and a fully equipped kitchen with a refrigerator and microwave; nearby activities include wine tasting and birdwatching.
Chesapeake Bay
07/20 – 07/27
$190/nighttotal: $1330 (7 )
Peek-a-boo Water Views! Port Haywood Home W/ Yard
2 4
house , Mathews
This Port Haywood house is located in Mathews, approximately 45 miles from Newport News/Williamsburg International Airport. This 900 square foot home offers two bedrooms, one bathroom, and accommodates up to nine guests with amenities including WiFi, air conditioning, and free on-site parking, plus an outdoor dining area and yard with water views.
9.8 315 reviews
Chesapeake Bay
08/23 – 08/28
$171/nighttotal: $855 (5 )
The Heron's Nest At Atlantic Marina
1 2
cottage , Lake Shore
This charming cottage is located in Pasadena, just steps from the beach on the Patapsco River, offering breathtaking water views and a peaceful escape. The cottage has consistently received excellent reviews from previous guests. The cottage has a spacious layout with 580 square feet of living space, one bedroom, one bathroom, and can accommodate up to four guests. It features a fully equipped kitchen, a comfortable living area, a private porch, and access to a swimming pool, making it perfect for families and groups seeking a relaxing getaway.
10 5 reviews
Chesapeake Bay
07/30 – 08/05
$253/nighttotal: $1518 (6 )
Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac
2 6
cottage , Piney Point
This Piney Point waterfront cottage offers two bedrooms, one bathroom, and sleeps six, providing easy access to the Piney Point Lighthouse and Patuxent River Naval Air Museum. The fully equipped kitchen includes a refrigerator, microwave, stove, and cooktop; amenities include air conditioning, Wi-Fi, laundry facilities, and a BBQ grill, plus smart TVs in each bedroom.
9.7 3 reviews
Chesapeake Bay
08/23 – 08/28
$209/nighttotal: $1045 (5 )
Midlong Term Rental Cozy Home At Mary Roberts
2 2
house , Newport News
This Stoney Brook Estates vacation home in Newport News offers convenient access to major attractions, located 10 miles from Busch Gardens & Water Country and 15 miles from Colonial Williamsburg. This 1100 square foot rental features two bedrooms, two bathrooms, air conditioning, a full kitchen with a dishwasher and oven, free Wifi, and free private parking, accommodating up to 10 guests with a 11:00 AM check-out.
9.0 286 reviews
Chesapeake Bay
10/01 – 10/05
$271/nighttotal: $1084 (4 )
Norfolk Beach Cottage Rental
3 3
cottage , Norfolk
This family-friendly cottage is located just 3 miles from Norfolk Beaches and Ocean View Beach and within 6 miles of Nauticus and Little Creek Beach. It offers an excellent location for exploring the area's attractions and enjoying the beautiful coastline. The cottage has received excellent user ratings, making it a popular choice for travelers. This charming 3-bedroom vacation rental sleeps up to 6 guests and is perfect for families. The cottage offers a variety of amenities, including a private swimming pool, a barbecue grill, and a spacious garden, allowing you to relax and enjoy your stay.
Chesapeake Bay
10/01 – 10/05
$166/nighttotal: $664 (4 )
The Haven
1 3
house , Dundalk
This house rental in Dundalk is located 5.1 miles from the Korean War Memorial and 6.4 miles from Fell's Point. The Haven offers 1600 square feet of living space, accommodating up to 9 guests with 1 bedroom, 2 bathrooms, a fully equipped kitchen, free WiFi, and private parking.
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
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.
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.
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.
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
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.
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.
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.
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
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?
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.
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.
9.8 187 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.
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
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.
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.
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.
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.