Villas and Beach houses in Chesapeake, VA

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Chesapeake, VA villas
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135 Villa rentals in Chesapeake, VA

Traveler-Approved Vacation Homes with a Pool in Chesapeake, VA

Choosing a vacation home in Chesapeake, VA with a pool means a private swim is always available.

Charming Quiet Carriage House - Chesapeake, VA
10 35 reviews
Chesapeake, VA
07/31 – 08/31
$113/nighttotal: $3503 (31 )

Charming Quiet Carriage House

1 2
house , Virginia Beach
This newly furnished apartment is located in a quiet wooded area just 8 miles from Virginia Beach, close to the PACC, sportsplex, shops, and restaurants. The property has received excellent ratings for user experience, location, and cleanliness.
This one-bedroom, one-bathroom apartment can accommodate up to 4 guests and features a new queen bed, a pull-out couch, a fully equipped kitchen, a washer and dryer, and a private garden. Enjoy a relaxing escape with modern amenities and a peaceful setting.
The Cove House - Chesapeake, VA
Chesapeake, VA
09/25 – 09/30
$360/nighttotal: $1800 (5 )

The Cove House

4 4
house , Chesapeake
This family-friendly apartment is located in a convenient district of Chesapeake, offering easy access to local attractions and amenities.
This 4-bedroom, 2-bathroom dwelling accommodates up to 10 guests and features a full kitchen, air conditioning, a swimming pool, garden, fitness center, and parking.

Best family friendly Chesapeake, VA villas and beach houses

Among the 135 accommodations in Chesapeake, VA, here are the 4 best family friendly villas and beach houses

3 Bd Townhome Near Historic Waterfront Portsmouth - Chesapeake, VA
9.3 106 reviews
Chesapeake, VA
06/23 – 06/25
$197/nighttotal: $394 (2 )

3 Bd Townhome Near Historic Waterfront Portsmouth

1 3
house , Portsmouth
This Portsmouth townhome is conveniently located just minutes from the Rivers Casino, the historic downtown district, and the Naval Shipyard, making it easy to explore the city's attractions. Guests have consistently rated the accommodation excellent for its cleanliness, location, and overall experience.
The townhome offers three bedrooms and one bathroom, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, air conditioning, a garden, and parking, ensuring a comfortable and enjoyable stay.
Spacious Home In Chesapeake - Chesapeake, VA
9.5 2 reviews
Chesapeake, VA
09/25 – 09/30
$427/nighttotal: $2135 (5 )

Spacious Home In Chesapeake

4 4
house , Chesapeake
This spacious Chesapeake, Virginia home is conveniently located approximately 7.5 miles from the Norfolk Botanical Garden, 17 miles from the Neptune Statue, and 5.4 miles from Topgolf Virginia Beach.
This 2,000-square-foot house features four bedrooms, three bathrooms, and can comfortably accommodate up to 14 guests, offering free Wi-Fi, a fully equipped kitchen, private parking, and a terrace.
Jefferson Abbey Ii - Chesapeake, VA
9.2 101 reviews
Chesapeake, VA
09/25 – 09/30
$193/nighttotal: $965 (5 )

Jefferson Abbey Ii

1 4
house , Chesapeake
This Chesapeake townhome is centrally located off I-64, within easy reach of major attractions in Hampton Roads, including the Oceanfront, Downtown Norfolk, Virginia Beach, military bases, dining, and shopping. It has very good user, location, and cleanliness ratings.
The townhome has two king master suites, one on the first level, and a queen sleeper sofa in the loft/office for additional sleeping space. It can accommodate up to 6 guests. It has modern updates, stylish design, a fully equipped kitchen, comfortable seating areas, keypad entry for self check-in, and a garden.
Virginia Beach Townhome - Chesapeake, VA
9.4 111 reviews
Chesapeake, VA
07/31 – 08/31
$111/nighttotal: $3441 (31 )

Virginia Beach Townhome

2 2
house , Virginia Beach
This 2-bedroom townhome in Virginia Beach is just 20 minutes from the Oceanfront, making it a convenient base for exploring the city's attractions. The house has consistently received excellent ratings for cleanliness, location, and overall guest experience.
The townhome comfortably accommodates up to 8 guests and features a fully equipped kitchen, washer and dryer, spacious parking, and access to owner-provided games and beach items. Guests can enjoy a relaxing garden and take advantage of the nearby beach and other attractions.

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Best Chesapeake, VA houses with parking

Cozy 2 Bdrm Cottage King Bed - Chesapeake, VA
8.2 4 reviews
Chesapeake, VA
08/16 – 08/27
$148/nighttotal: $1628 (11 )

Cozy 2 Bdrm Cottage King Bed

1 4
house , Portsmouth
This 2-bedroom cottage in Portsmouth is located 12 miles from Norfolk Botanical Garden and Topgolf Virginia Beach, and 23 miles from the King Neptune Statue.
This accommodation features a fully equipped kitchen, complimentary Wi-Fi, air conditioning, private parking, and accommodates up to 9 guests with a 10:00 AM check-out.
Portsmouth Waterfront Vacation Rental W/ Deck - Chesapeake, VA
Chesapeake, VA
09/25 – 09/30
$440/nighttotal: $2200 (5 )

Portsmouth Waterfront Vacation Rental W/ Deck

3 4
house , Portsmouth
This Portsmouth waterfront rental offers scenic views and is located 11 miles from Norfolk Botanical Garden and 24 miles from the King Neptune Statue on the Boardwalk.
This 1530 square foot house features 3 bedrooms, 2 bathrooms, a full kitchen with a dishwasher and coffee machine, an on-site bar, and parking, accommodating up to 15 guests with free WiFi and air conditioning.
Waterfront Oasis With Fenced Yard - Chesapeake, VA
9.7 295 reviews
Chesapeake, VA
09/25 – 09/30
$305/nighttotal: $1525 (5 )

Waterfront Oasis With Fenced Yard

1 4
house , Chesapeake
This charming townhouse in Chesapeake offers a peaceful setting with a backyard overlooking a small lake. The property has received excellent ratings for its cleanliness, location, and overall experience.
The home features an open floor plan, accommodating up to 8 guests comfortably. It includes modern amenities such as a fully equipped kitchen, laundry facilities, and air conditioning, ensuring a comfortable and enjoyable stay.
98 M² House ∙ 1 Bedroom ∙ 1 Guest - Chesapeake, VA
Chesapeake, VA
07/19 – 10/18
$153/nighttotal: $13923 (91 )

98 M² House ∙ 1 Bedroom ∙ 1 Guest

1 1
house , Norfolk
House listing for 1 person. You will be based in Norfolk.
Facilities and services include a dish washer, a washing machine and a wheelchair friendly access. Take advantage of the air conditioning in this house in Norfolk.

Best Chesapeake, VA houses with a garden

Comfortable & Private 2 Bedrm Cottage W/ King Bed. - Chesapeake, VA
9.4 20 reviews
Chesapeake, VA
07/09 – 07/14
$249/nighttotal: $1245 (5 )

Comfortable & Private 2 Bedrm Cottage W/ King Bed.

2 5
cottage , Portsmouth
This charming cottage is located in Portsmouth, just a short distance from Rivers Casino Portsmouth and Portsmouth City Park. It has earned excellent ratings from previous guests.
The cozy home offers 2 bedrooms and 1 bathroom, with enough space to accommodate up to 5 guests. Enjoy a fully equipped kitchen, free Wi-Fi, a DVD player, and a private garden with a terrace.
Country Escape - Next Door - Hidden Gem - Chesapeake, VA
10 76 reviews
Chesapeake, VA
09/25 – 09/30
$161/nighttotal: $805 (5 )

Country Escape - Next Door - Hidden Gem

1 4
house , Chesapeake
This Chesapeake home, aptly named "Next Door," is situated in a rural area, just a short drive from the Chesapeake Bay and local beaches. It has received excellent ratings for its location, cleanliness, and overall experience.
The house, located above a garage, offers a unique "treehouse" feel with a spacious, open concept floor plan accommodating up to 6 guests. It features a well-equipped kitchen, laundry facilities, and a large backyard with a deck, grill, and communal picnic area with a playground, sandbox, fire pit, and outhouse.
Best Temporary Rental In Chesapeake - Chesapeake, VA
9.7 54 reviews
Chesapeake, VA
09/25 – 09/30
$243/nighttotal: $1215 (5 )

Best Temporary Rental In Chesapeake

1 4
house , Chesapeake
This Chesapeake townhome is conveniently located in the Greenbrier area, offering easy access to shopping, restaurants, and the interstate. It boasts excellent user, location, and cleanliness ratings.
The two-bedroom, two-bathroom townhome comfortably sleeps four guests. Amenities include a fully equipped kitchen, air conditioning, a garden, and parking.
The Western Branch Professionals Townhome - Chesapeake, VA
9.5 21 reviews
Chesapeake, VA
09/25 – 09/30
$293/nighttotal: $1465 (5 )

The Western Branch Professionals Townhome

1 4
house , Chesapeake
This Chesapeake townhome offers a central location, just 10 minutes from Chesapeake Square Mall and under an hour from Busch Gardens and Virginia Beach.
The remodeled three-bedroom, two-and-a-half-bathroom house sleeps six, features a fully equipped kitchen with stainless steel appliances, in-unit laundry, and free Wi-Fi throughout.
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