Find short term rentals in Chesapeake, VA at the best prices

561 available short term rental offers

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Chesapeake, VA short term rentals
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Best Short term and Weekly rentals in Chesapeake, VA

Best Chesapeake, VA luxury short term rentals

Country Escape Home In The Woods- Chesapeake, Va - Chesapeake, VA
10 24 reviews
Chesapeake, VA
25/09 – 30/09
$256/nighttotal: $1280 (5 )

Country Escape Home In The Woods- Chesapeake, Va

3 4
apartment , Chesapeake
This apartment is situated in a peaceful rural area of Chesapeake, Virginia, just 2.4 kilometres from Ballahack Airsoft Field and other attractions. It has received excellent user ratings, making it a popular choice for travellers.
The apartment offers 121 square metres of space, comfortably accommodating up to six guests in its three bedrooms and one bathroom. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden, a spa, parking, and access to the internet.

Best Chesapeake, VA Short term rentals with a jacuzzi

Among the 561 accommodations in Chesapeake, VA, here are the 4 best rentals with a jacuzzi

Serene Lodging With Indoor Fireplace - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
$140/nighttotal: $18060 (129 )

Serene Lodging With Indoor Fireplace

2 2
apartment , Virginia Beach
This Northwest Virginia Beach holiday home is situated 1.8km from Virginia Wesleyan University, within 5km of Sentara Leigh Hospital and Norfolk Premium Outlets.
This 71-square-metre property offers two bedrooms, one bathroom, sleeps two guests, and includes a fully equipped kitchen, Jacuzzi, free Wi-Fi, and in-unit laundry facilities.
Your Best Cozy Room In The Area - Chesapeake, VA
9.2 12 reviews
Chesapeake, VA
24/07 – 26/07
$217/nighttotal: $434 (2 )

Your Best Cozy Room In The Area

1 4
apartment , Virginia Beach
This Virginia Beach guesthouse is conveniently located within a 10-15 minute drive (approx. 16-24 km) of Virginia Beach oceanfront, the town centre, Norfolk International Airport, and Downtown Norfolk.
Offering a private room for two guests, this affordable bed and breakfast features a shared bathroom, a garden, jacuzzi, parking, and Wi-Fi; three bedrooms are available in total.
Newly Remodeled 2 Bedroom Duplex - Chesapeake, VA
10 2 reviews
Chesapeake, VA
31/07 – 31/08
$199/nighttotal: $6169 (31 )

Newly Remodeled 2 Bedroom Duplex

2 2
apartment , Chesapeake
This newly renovated flat is located in the Great Bridge neighbourhood of Chesapeake, a quiet area just a short drive from Jillian's Billiards and the Currituck County Welcome Center. The apartment is ideal for families or groups of up to 3 people, offering 2 bedrooms and 1 bathroom.
The flat comes equipped with a modern kitchen, including a fridge, microwave, and dishwasher, as well as a jacuzzi, parking, and free Wi-Fi. Enjoy the convenience of a washer and dryer, and relax on the comfortable sofas in front of the 65-inch Smart TV.
Cute 4 Bed / 2.5 Bath Home W/ Pool - Sleeps 12! 30 Night Min - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
$235/nighttotal: $30315 (129 )

Cute 4 Bed / 2.5 Bath Home W/ Pool - Sleeps 12! 30 Night Min

4 2
apartment , Virginia Beach
This four-bedroom home is located in a peaceful neighbourhood just 2 kilometres from Town Centre and the Virginia Beach Oceanfront, and a short distance from Mount Trashmore Park. The property is ideal for families or groups of friends, comfortably sleeping 12 guests across its six beds.
The apartment offers a range of amenities, including a fully equipped kitchen, air conditioning, a private swimming pool, a Jacuzzi, and parking for four cars. Guests can also enjoy the spacious backyard with a barbecue area, perfect for relaxing evenings.

Frequently Asked Questions about short term rentals in Chesapeake, VA

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Best family friendly Chesapeake, VA Short term rentals

Among the 561 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals

Home Sweet Home 2 - Chesapeake, VA
10 12 reviews
Chesapeake, VA
27/06 – 04/07
$341/nighttotal: $2387 (7 )

Home Sweet Home 2

1 2
apartment , Virginia Beach
This Virginia Beach guesthouse, offering a Caribbean-themed experience, is conveniently located in [Insert specific district/area of Virginia Beach and proximity to landmarks, e.g., "the ViBe Creative District, approximately 2km from the Virginia Beach Boardwalk"].
The self-catering property features a queen-size bed, shared kitchen facilities, a private bathroom, sleeps up to four guests and includes a full Caribbean breakfast (notification required) for a small tip.
5 Mi To Nas Oceana: Townhome W/ Fenced Yard! - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
$172/nighttotal: $22188 (129 )

5 Mi To Nas Oceana: Townhome W/ Fenced Yard!

3 2
apartment , Virginia Beach
This Virginia Beach beachfront property offers direct oceanfront access and is conveniently located near Pacific Avenue and Greenbrier Mall, with Sandbridge Beach and First Landing State Park also within easy reach, although precise distances aren't specified.
This three-bedroom, two-and-a-half-bathroom house boasts 134 square metres of floor space, comfortably accommodating six guests and featuring a full kitchen, private patio, and in-unit laundry facilities; nearby water activities such as motorboat tours are also available.
Country Escape Next Door Rental - Sleeps 6 - Stay Upstairs In The Trees - Chesapeake, VA
10 15 reviews
Chesapeake, VA
25/09 – 30/09
$229/nighttotal: $1145 (5 )

Country Escape Next Door Rental - Sleeps 6 - Stay Upstairs In The Trees

1 4
B&B , Chesapeake
"Next DOOR" is a charming self-catering property situated in a tranquil rural area of Chesapeake, just 10km from the Great Dismal Swamp National Wildlife Refuge and 15km from Oak Grove Lake Park. It has received excellent guest reviews, praising its unique location and family-friendly atmosphere.
This one-bedroom property spans 102 square metres, comfortably accommodating up to six guests. The well-equipped kitchen, spacious garden with playground, and large deck with barbecue make it perfect for families seeking a relaxing getaway in the heart of Chesapeake.
Sojourn At Colley Manor Unit 5 - Chesapeake, VA
Chesapeake, VA
31/07 – 31/08
$202/nighttotal: $6262 (31 )

Sojourn At Colley Manor Unit 5

2 2
apartment , Norfolk
This Ghent, Norfolk flat is situated in the historic Ghent district, close to Colley Avenue's restaurants and cafes, with easy access to Norfolk city centre via public transport and a short drive (approximately 16km) to Virginia Beach.
The 84 square metre self-catering apartment sleeps four, features two bedrooms, one bathroom, a fully equipped kitchen including a dishwasher, air conditioning, parking, and contactless check-in; a travel cot and high chair are available for a fee.

Best Chesapeake, VA lodging with parking

Comfortable Retreat W/ Backyard & Parking - Chesapeake, VA
10 1 review
Chesapeake, VA
02/07 – 05/07
$500/nighttotal: $1500 (3 )

Comfortable Retreat W/ Backyard & Parking

2 5
apartment , Portsmouth
This two-bedroom, one-bathroom duplex in Brighton, Portsmouth, is situated adjacent to the naval shipyard, offering a five-minute walk to the Portsmouth Naval Shipyard and a ten-minute drive to downtown Portsmouth's restaurants and entertainment.
This family-friendly and pet-friendly flat provides accommodation for up to six guests, featuring a fully equipped kitchen with a fridge and microwave, air conditioning, on-site parking for one vehicle, and fast Wi-Fi, with self-check-in available via a smart lock.
Cozy 4 Bed 2 Bath Home - Norfolk, Centrally Located - Chesapeake, VA
9.6 4 reviews
Chesapeake, VA
12/10 – 18/02
$250/nighttotal: $32250 (129 )

Cozy 4 Bed 2 Bath Home - Norfolk, Centrally Located

4 2
apartment , Norfolk
This four-bedroom house in central Norfolk offers convenient access to downtown attractions and is a short drive from the Virginia Beach oceanfront, with proximity to Town Point Park and the Pagoda and Oriental Garden.
This pet-friendly property accommodates up to eight guests and features a fully equipped kitchen with a microwave oven and dishwasher, air conditioning, parking, and two bathrooms, ensuring a comfortable stay with amenities such as an iron and hair dryer.
Va Beach Zen Retreat House - Chesapeake, VA
8.1 9 reviews
Chesapeake, VA
29/06 – 03/08
$233/nighttotal: $8155 (35 )

Va Beach Zen Retreat House

1 2
B&B , Virginia Beach
The VA Beach Zen retreat house is located in Virginia Beach, just a short drive from Topgolf Virginia Beach and Mount Trashmore Park, making it a convenient base for exploring the area. The property has received very good user ratings and excellent ratings for location and cleanliness.
The retreat offers a comfortable and relaxing stay with a 149 square metre floor area. Guests can enjoy a shared lounge area, a garden, and a terrace, as well as a fully equipped kitchen with a dishwasher, air conditioning, free Wi-Fi, and private parking.
Sojourn At Colley Manor Unit 3 - Chesapeake, VA
10 1 review
Chesapeake, VA
31/07 – 31/08
$203/nighttotal: $6293 (31 )

Sojourn At Colley Manor Unit 3

2 2
apartment , Norfolk
This Ghent flat in Norfolk is situated near Colley Avenue, offering easy walking access to restaurants and cafes, and is a short drive (a few kilometres) from Virginia Beach and Ocean View.
The 81-square-metre (870 sq ft) self-catering property sleeps four, features two bedrooms, one bathroom, and includes amenities such as a dishwasher, air conditioning, parking, and Wi-Fi; a travel cot and high chair are available on request.
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