Chesapeake, VA short term rentalscozycozy

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790 available short term rental offers

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Best Short term and Weekly rentals in Chesapeake, VA

Centrally Located Hampton Roads Home W/ Game Room! - Chesapeake, VA
10 1 review
Chesapeake, VA
2 4
$500/nighttotal: $3500 (7 )

Centrally Located Hampton Roads Home W/ Game Room!

apartment - Portsmouth
This family and pet-friendly flat in Portsmouth offers convenient access, situated 4 kilometres from Downtown Norfolk and 33 kilometres from First Landing State Park.
This 269 square metre residence accommodates up to 8 guests across 4 bedrooms and 3 bathrooms, featuring a game room with a pool table and arcade games, a fenced garden with a deck, patio, and fire pit, a dry bar, record player, and a well-equipped kitchen.
Spiral Loft - Chesapeake, VA
8.9 68 reviews
Chesapeake, VA
2 2
$174/nighttotal: $1392 (8 )

Spiral Loft

apartment - Norfolk
This Norfolk apartment is situated in the Ghent Historic District, a short walk from Norfolk's commercial centre, offering easy access to the waterfront and historical sites along former trolley routes.
The self-catering flat, sleeping two guests, includes a dishwasher, air conditioning, parking, and benefits from excellent guest reviews for cleanliness and location.
Spacious, 2 Master Suites, Sleeps 6-8, 2.5 Baths - Chesapeake, VA
10 13 reviews
Chesapeake, VA
8 2
$306/nighttotal: $2142 (7 )

Spacious, 2 Master Suites, Sleeps 6-8, 2.5 Baths

apartment - Chesapeake
This two-bedroom flat in Chesapeake offers a family-friendly stay with internet, air conditioning, and a well-equipped kitchen, featuring a fridge, freezer, microwave, and dishwasher.
Sleeping up to eight guests, this accommodation boasts two master suites with en-suite bathrooms, flexible sleeping arrangements including king and queen beds, a queen air mattress, and an extendable dining table.
Your Home Away From Home And Near Va Beach - Chesapeake, VA
8.8 12 reviews
Chesapeake, VA
10 4
$735/nighttotal: $2205 (3 )

Your Home Away From Home And Near Va Beach

apartment - Portsmouth
This four-bedroom Portsmouth house, sleeping up to ten guests, is situated in a quiet neighbourhood, approximately 24km from Portsmouth Naval Hospital and 40km from Virginia Beach.
The property boasts a spacious interior with a large living room, dining room, office, fully equipped kitchen including dishwasher, two bathrooms (one with Jacuzzi), Wi-Fi, Roku TVs, and private gardens with parking; ideal for families or groups visiting the area's military bases.
Riverfront 3br Retreat  Near Rivers Casino - Chesapeake, VA
9.6 68 reviews
Chesapeake, VA
3 3
$445/nighttotal: $1335 (3 )

Riverfront 3br Retreat Near Rivers Casino

apartment - Portsmouth
This Portsmouth house rental is peacefully situated near the Elizabeth River, a short distance (approximately 1.3 km) from Historic Olde Towne Portsmouth and an 8-minute drive (approximately 5 km) from Rivers Casino Portsmouth.
The three-bedroom, two-bathroom property sleeps six guests, boasting a fully equipped kitchen with dishwasher, in-home laundry facilities, air conditioning, parking, and high-speed Wi-Fi; enjoy the spacious backyard and proximity to local shops and restaurants.
The Couples $Pot @ The Dock Near Casino - Chesapeake, VA
9.9 28 reviews
Chesapeake, VA
2 2
$277/nighttotal: $1939 (7 )

The Couples $Pot @ The Dock Near Casino

apartment - Portsmouth
This 1928 property in Portsmouth's historic Cradock neighbourhood offers easy access to Portsmouth city centre, Norfolk and Virginia Beach (a short drive away), and is within 5km of a casino.
The two-bedroom, one-bathroom house sleeps four, features a fully equipped kitchen with fridge, freezer and microwave, air conditioning, parking, a private fenced backyard, and self-check-in via keypad.
Simply Amazing In Chesapeake - Chesapeake, VA
10 40 reviews
Chesapeake, VA
5 3
$545/nighttotal: $1635 (3 )

Simply Amazing In Chesapeake

apartment - Chesapeake
This Chesapeake property is conveniently located just 5-10 kilometres from Greenbrier Mall, various shopping plazas, and restaurants, making it a great base for exploring the area. It also enjoys a prime position, being only 15 kilometres from the Virginia Beach oceanfront and 10 kilometres from Ocean View in Norfolk. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
This spacious home offers three bedrooms and two bathrooms, comfortably accommodating up to eight guests. The fully equipped kitchen features a fridge, freezer, microwave, and dishwasher, alongside a garden, parking, air conditioning, and internet access, ensuring a comfortable and enjoyable stay.
The Southern Magnolia | 2br/1bth Home - Chesapeake, VA
9.6 11 reviews
Chesapeake, VA
2 2
$251/nighttotal: $2008 (8 )

The Southern Magnolia | 2br/1bth Home

apartment - Chesapeake
This Chesapeake apartment, situated in a quiet residential neighbourhood near Highway 464, offers easy access to Norfolk city centre (16km), Greenbrier Mall (8km), and various hospitals within an 8-13km radius.
The ground-floor, fully furnished flat comprises two bedrooms, one bathroom, and accommodates up to four guests, boasting a private screened porch overlooking a 200-year-old Magnolia tree and waterfront views, plus access to a shared waterfront terrace with a fire pit and grilling area; in-unit laundry, a fully equipped kitchen, and reserved parking are also included.
Nyakio Suite - Chesapeake, VA
Chesapeake, VA
4 2
$556/nightfor 1 night

Nyakio Suite

apartment - Chesapeake
This Nyakio Suite flat is situated on the first floor in a quiet family district of Chesapeake, Virginia, offering a tranquil retreat.
This pet-friendly residence accommodates up to four guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a decorative fireplace, and a private balcony overlooking a seasonal shared swimming pool, with internet and laundry facilities available.
Cavalier Manor: Pool, Luxury Home, & Scenic Views - Chesapeake, VA
9.7 77 reviews
Chesapeake, VA
10 5
$2262/nighttotal: $6786 (3 )

Cavalier Manor: Pool, Luxury Home, & Scenic Views

apartment - Portsmouth
This five-bedroom apartment is situated in Cavalier Manor on Crystal Lake, a short drive from Portsmouth's historic downtown and waterfront. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The apartment comfortably accommodates up to 14 guests, offering plenty of space for families or groups of friends. It boasts a private pool and hot tub, an outdoor kitchen, fireplaces, and stunning water views, making it the perfect place to relax and enjoy the beautiful surroundings.
Studio Apartment - Chesapeake, VA
9.9 38 reviews
Chesapeake, VA
2 1
$122/nighttotal: $854 (7 )

Studio Apartment

B&B - Chesapeake
This Chesapeake guesthouse is located above a detached garage, approximately 32 kilometres from the Norfolk Naval Shipyard.
The self-contained unit offers a queen-sized bed, full bathroom with shower, free Wi-Fi, and a TV, sleeping up to two guests.
Sojourn At Colley Manor Unit 6 - Chesapeake, VA
Chesapeake, VA
2 2
$787/nighttotal: $44072 (56 )

Sojourn At Colley Manor Unit 6

apartment - Norfolk
Colley Manor Unit 6, a Norfolk apartment, is located approximately 10 kilometres from Norfolk International Airport and 11 kilometres from the Norfolk Botanical Garden, offering convenient access to these attractions.
This two-bedroom flat, boasting 93 square metres of floor space, comfortably sleeps six guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, parking, and free Wi-Fi and cable TV.

Best Chesapeake, VA luxury short term rentals

3br, 6 Beds  Prime Stay Near Rivers Casino! - Chesapeake, VA
10 2 reviews
Chesapeake, VA
2 3
$526/nighttotal: $3682 (7 )

3br, 6 Beds Prime Stay Near Rivers Casino!

apartment - Portsmouth
This Portsmouth holiday home is situated within 5km of the Rivers Casino Portsmouth, the Commodore Theatre, and the Virginia Sports Hall of Fame, offering easy access to these attractions.
The three-bedroom property sleeps six guests and boasts a fully equipped kitchen with appliances including a dishwasher, a garden, parking, and free Wi-Fi, alongside a washing machine and barbecue facilities.

Best Chesapeake, VA Short term rentals with a jacuzzi

Among the 790 accommodations in Chesapeake, VA, here are the 4 best rentals with a jacuzzi

Luxury Lakefront Estate & Guest House W/ Pool - Chesapeake, VA
10 12 reviews
Chesapeake, VA
10 6
$2139/nighttotal: $6417 (3 )

Luxury Lakefront Estate & Guest House W/ Pool

apartment - Portsmouth
This luxurious lakefront estate sits on Crystal Lake, offering a tranquil retreat just 10km outside of Portsmouth, providing easy access to the city's attractions. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a top choice for discerning travellers.
The estate features a grand main house and a separate guest house, accommodating up to 16 guests. Guests can enjoy a refreshing dip in the pool, relax in the Jacuzzi, or prepare meals in the gourmet kitchen, all while taking in stunning lake views.
The Chesapeake Gray  Historical Waterside District 20 Mins To Oceanfront - Chesapeake, VA
9.4 8 reviews
Chesapeake, VA
2 3
$642/nighttotal: $5136 (8 )

The Chesapeake Gray Historical Waterside District 20 Mins To Oceanfront

apartment - Norfolk
This Norfolk apartment is located within easy reach of both Waterside Festival Marketplace and Virginia Beach Town Center, offering a convenient base for exploring the city and its surroundings. The apartment is just a short drive from the beach, providing a perfect blend of urban convenience and coastal charm.
The property is a spacious three-bedroom home that comfortably sleeps six guests. It offers a modern kitchen, a private backyard with a patio, and a jacuzzi, ideal for relaxing after a day of exploring the local attractions.
Free Breakfast. Indoor Pool & Hot Tub. Near The Virginia Beach Business District! - Chesapeake, VA
Chesapeake, VA
2 1
$348/nighttotal: $2784 (8 )

Free Breakfast. Indoor Pool & Hot Tub. Near The Virginia Beach Business District!

apartment - Chesapeake
This Chesapeake condo is situated a 9-minute walk from the Chesapeake Conference Centre and a 3-minute drive (approximately 1.6 km) from Greenbrier Mall, offering easy beach access.
The one-bedroom, one-bathroom apartment sleeps four guests and includes a fully equipped kitchen, in-unit laundry, a swimming pool, jacuzzi, and free Wi-Fi; nearby attractions include the Veterans United Home Loans Amphitheatre and Waterside District.
Your Best Cozy Room In The Area - Chesapeake, VA
9.0 21 reviews
Chesapeake, VA
4 1
$222/nightfor 1 night

Your Best Cozy Room In The Area

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.

Frequently Asked Questions about short term rentals in Chesapeake, VA

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Best family friendly Chesapeake, VA Short term rentals

Among the 790 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals

Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews
Chesapeake, VA
5 4
$640/nighttotal: $1920 (3 )

Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8

apartment - Portsmouth
This holiday home is located in Portsmouth, just 1.5 km from Rivers Casino Portsmouth, and within 10 km of Portsmouth City Park and Frank D Lawrence Stadium. It has consistently received excellent user ratings, making it a popular choice for travellers.
The property offers 93 square metres of space and can comfortably accommodate up to 6 guests in its 3 bedrooms. The kitchen comes equipped with a fridge, microwave, oven, and dishwasher, while the garden provides a relaxing outdoor space. Guests can also enjoy free Wi-Fi, air conditioning, a terrace, and parking.
Modern, Homely 3-bdrm|wparking|centrally  Located. - Chesapeake, VA
9.4 246 reviews
Chesapeake, VA
4 3
$337/nightfor 1 night

Modern, Homely 3-bdrm|wparking|centrally Located.

apartment - Portsmouth
This apartment is situated in Portsmouth, within walking distance of shops, restaurants and amenities, and just a few kilometres from the historic downtown area and the Norfolk Zoo. The apartment has received excellent ratings for cleanliness and user experience, with a very good location rating.
The apartment offers three bedrooms and two bathrooms, comfortably accommodating up to eight guests. It comes equipped with a kitchen including a fridge, freezer, microwave and dishwasher, as well as air conditioning, a garden and parking.
Country Escape Home In The Woods- Chesapeake, Va - Chesapeake, VA
10 26 reviews
Chesapeake, VA
5 3
$350/nighttotal: $1050 (3 )

Country Escape Home In The Woods- Chesapeake, Va

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.
Cozy Ranch Home, Centrally Located Near Chicks Beach! - Chesapeake, VA
8.6 9 reviews
Chesapeake, VA
2 3
$607/nighttotal: $4856 (8 )

Cozy Ranch Home, Centrally Located Near Chicks Beach!

apartment - Virginia Beach
This Virginia Beach farmhouse, situated in the Northwest neighbourhood, is a 5-minute drive (approximately 3.2km) from Highway 264, offering easy access to the Virginia Beach Town Centre and other attractions.
Sleeping up to eight guests in three bedrooms and one bathroom, this self-catering property boasts a fully equipped kitchen, a relaxing backyard with a fire pit, and is conveniently located near the Veterans United Home Loans Amphitheatre and Ocean Breeze Waterpark.

Best Chesapeake, VA lodging with parking

Cozy Rambler - 3 Bd 2 Bath Home Full Of Charm - Chesapeake, VA
9.4 92 reviews
Chesapeake, VA
5 3
$376/nighttotal: $1128 (3 )

Cozy Rambler - 3 Bd 2 Bath Home Full Of Charm

apartment - Portsmouth
This apartment in Portsmouth is conveniently located just a short distance from the city centre, making it easy to explore its historic attractions and vibrant waterfront. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay for guests.
The apartment offers ample space for families or groups of up to six people, with two bathrooms for added convenience. Guests can enjoy a fully equipped kitchen, air conditioning, covered parking, and access to a private backyard, perfect for relaxing after a day of exploring the city.
The Manor- Extended Stays - Chesapeake, VA
10 8 reviews
Chesapeake, VA
5 3
$481/nighttotal: $1443 (3 )

The Manor- Extended Stays

apartment - Chesapeake
This Chesapeake apartment, near Greenbrier Mall, offers easy access to the Oceanfront, Norfolk Waterside, and Norfolk Outlets.
The four-bedroom, two-bathroom property sleeps eight, features a recently remodelled kitchen with modern appliances, a 65-inch TV, free Wi-Fi, and self check-in; nearby attractions include the Chesapeake Jubilee and Deep Creek Locks.
Portsmouth Waterfront Home - Patio + River Views - Chesapeake, VA
9.0 7 reviews
Chesapeake, VA
8 3
$425/nighttotal: $2975 (7 )

Portsmouth Waterfront Home - Patio + River Views

apartment - Portsmouth
This detached property in Portsmouth offers convenient access to the Waterside District and Greenbrier Mall, and is within easy reach of the United States Lightship Portsmouth and the Children's Museum of Virginia.
This three-bedroom, two-bathroom accommodation sleeps up to six guests and includes a kitchen with a fridge, microwave, and dishwasher, air conditioning, WiFi, and a garden, with dogs welcome.
Home Sharing: Luxurious 3600sf 6br 4ba Home - Chesapeake, VA
9.7 232 reviews
Chesapeake, VA
11 5
$938/nighttotal: $8442 (9 )

Home Sharing: Luxurious 3600sf 6br 4ba Home

apartment - Virginia Beach
This upscale guesthouse is situated in the peaceful Kempsville neighbourhood of Virginia Beach, just a short drive from the Norfolk Outlets Mall, Norfolk Airport, and the Virginia Beach oceanfront. It boasts excellent ratings for location, cleanliness, and overall user experience.
The property features five bedrooms and four bathrooms, comfortably accommodating up to 15 guests. Guests can enjoy a fully equipped kitchen, a large deck overlooking a private garden, a pool table, and a range of modern amenities, including Roku TVs in every room, a fireplace, a gas grill, complimentary Wi-Fi, and self check-in with an electronic keypad.
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