Find short term rentals in Chesapeake, VA at the best prices
561 available short term rental offers
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Best Short term and Weekly rentals in Chesapeake, VA
9.8 59 reviews
Chesapeake, VA
09/07 – 14/07
$608/nighttotal: $3040 (5 )
The Bird’s Nest
1 5
apartment , Chesapeake
This apartment is located in the Great Bridge area of Chesapeake, just 32 kilometres from the oceanfront, 8 kilometres from the interstate, and 10 kilometres from Greenbriar Mall, offering a peaceful retreat with a country feel despite its proximity to urban amenities. The property has received excellent ratings for location, cleanliness, and user experience. The self-catering property can accommodate up to 8 guests and boasts a spacious outdoor area with a large fenced yard and an open field. It also features a tree house, a gazebo with an extension cord for lighting, and a variety of amenities including a Jacuzzi, a garden, and parking.
9.4 145 reviews
Chesapeake, VA
31/07 – 31/08
$189/nighttotal: $5859 (31 )
Downtown Corner Of W. Bute & Dunmore Streets
1 2
apartment , Norfolk
This one-bedroom flat is situated in a historic neighbourhood in Norfolk, just a few hundred metres from cobblestone streets, gourmet restaurants and the YMCA, and within easy walking distance of the Chrysler Museum of Art. It has received excellent ratings for its location, cleanliness and overall user experience. The flat can accommodate up to four guests and offers a range of amenities including a well-equipped kitchen, air conditioning, parking, and internet access. Guests can enjoy the outdoor space with benches on three sides of the building, perfect for relaxing or people-watching, and the flat also welcomes small, well-behaved pets.
9.6 169 reviews
Chesapeake, VA
12/10 – 18/02
$181/nighttotal: $23349 (129 )
5 Minutes To The Casino!family Sized Home 3 Bedroom With Patio And A Game Room
3 2
apartment , Portsmouth
This Portsmouth apartment is conveniently located just four minutes from Rivers Casino and fifteen minutes from the Waterside District, offering easy access to a range of attractions. It has consistently received excellent ratings for location, cleanliness, and overall user experience. The three-bedroom flat, spanning 130 square metres, comfortably sleeps up to eight guests. It boasts a fully equipped kitchen, a garden, a spa, a tennis court, and a range of entertainment options, including a pool table, darts, and a fire pit.
Chesapeake, VA
27/06 – 04/07
$133/nighttotal: $931 (7 )
Best Night
1 2
apartment , Virginia Beach
This furnished single room is located centrally in Virginia Beach, offering easy access to key districts and local attractions within a few kilometres. This accommodation provides a peaceful base for two guests with internet, air conditioning, a kitchen, and shared bathroom facilities in a townhouse setting.
Chesapeake, VA
27/06 – 04/07
$410/nighttotal: $2870 (7 )
Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood.
1 2
apartment , Chesapeake
This one-bedroom flat is located in Chesapeake, just a short distance from Norfolk's waterfront and a 32-kilometre drive from Virginia Beach's oceanfront. The surrounding area is quiet and offers easy access to local restaurants, supermarkets, and the city centre. The flat is spacious and comfortably accommodates up to four guests. It comes with free curbside parking, air conditioning, internet access, and a relaxing front porch.
9.6 28 reviews
Chesapeake, VA
31/07 – 31/08
$198/nighttotal: $6138 (31 )
Cozy Portsmouth Getaway 2br/1ba
1 2
apartment , Portsmouth
This two-bedroom house, situated in Portsmouth, Virginia's Port Norfolk Historic District, offers convenient access to local attractions. The property sleeps six, features a fully equipped kitchen with fridge and microwave, plus a backyard, air conditioning, high-speed Wi-Fi, and a washer/dryer.
9.2 52 reviews
Chesapeake, VA
02/07 – 05/07
$421/nighttotal: $1263 (3 )
Duplex W/fast Wi-fi & Stocked Kitchen
1 5
apartment , Portsmouth
This two-bedroom apartment is conveniently located in Portsmouth, Virginia, just a short walk from the Portsmouth Shipyard and a quick drive to downtown restaurants, the Naval Medical Center, and other attractions. The surrounding area offers a mix of residential and commercial spaces, providing a peaceful yet convenient setting for your stay. The apartment comfortably accommodates up to seven guests with its two bedrooms and one bathroom, perfect for families or groups. It features a fully equipped kitchen, air conditioning, private parking, and fast Wi-Fi, ensuring a comfortable and enjoyable stay.
Chesapeake, VA
31/07 – 31/08
$133/nighttotal: $4123 (31 )
Charming, Cozy, Furnished Studio
1 2
apartment , Norfolk
This Ghent, Norfolk studio apartment is situated a short distance (approximately 1.8km) from Sentara Norfolk General Hospital, Eastern Virginia Medical School, and The Children's Hospital of King's Daughters, offering convenient access to these institutions and the historic Ghent district. The self-catering unit sleeps two guests and includes a kitchen, air conditioning, parking, high-speed internet, and on-site laundry facilities; nearby attractions include downtown Ghent's entertainment options.
10 21 reviews
Chesapeake, VA
12/10 – 18/02
$326/nighttotal: $42054 (129 )
Fully Renovated And Modernized Home In Chesapeake
3 2
apartment , Chesapeake
This Chesapeake apartment is conveniently located just 2 kilometres from Portlock Galleries at SoNo and an 8-minute drive from Greenbrier Mall. It has received excellent guest reviews, making it a popular choice for travellers. The apartment has 3 bedrooms and 3 bathrooms, comfortably accommodating up to 8 guests. The property comes with a range of features, including a Smart TV, Wi-Fi, parking, and a barbecue area, providing everything you need for a comfortable stay.
10 1 review
Chesapeake, VA
02/07 – 05/07
$472/nighttotal: $1416 (3 )
Duplex W/fast Wi-fi & Stocked Kitchen
2 5
apartment , Portsmouth
This 2-bedroom, 1-bathroom duplex in Portsmouth's Brighton district offers proximity to the Portsmouth Shipyard, just 500 meters away, and is a 10-minute drive from the city centre's amenities. This family-friendly flat accommodates up to 7 guests, featuring a fully equipped kitchen with a fridge and microwave, air conditioning, free Wi-Fi, and on-site parking, making it ideal for shipyard workers or families visiting Portsmouth.
This private upstairs flat in historic Westhaven, Portsmouth, is conveniently located 4 kilometres from Rivers Casino, 2 kilometres from Portsmouth City Park, and offers proximity to the Commodore Theatre and Portsmouth Naval Shipyard Museum. This two-bedroom apartment accommodates up to four guests, featuring a kitchenette, a full-size washer and dryer, air conditioning, internet, and private off-street parking for one vehicle.
9.1 124 reviews
Chesapeake, VA
08/07 – 13/07
$291/nighttotal: $1455 (5 )
Beautiful 3 Bedroom Apt In Historic Parkview
3 5
apartment , Portsmouth
This three-bedroom duplex is located in a peaceful neighbourhood in Portsmouth, just 10km from Waterside and 15km from Virginia Beach. The apartment has received excellent ratings for cleanliness and location, with guests praising its quiet and established surroundings. The property can accommodate up to six guests and is equipped with modern amenities such as granite countertops, luxury vinyl flooring, and stainless steel appliances. Guests can enjoy the convenience of parking, internet access, and air conditioning, along with a well-equipped kitchen.
Best Chesapeake, VA luxury short term rentals
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
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.
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.
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.
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
What are the best short term rentals in Chesapeake, VA?
Best family friendly Chesapeake, VA Short term rentals
Among the 561 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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.
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.
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.