This private in-law suite offers direct access to the Elizabeth River, situated on a 1.5-hectare property in a tranquil area of Chesapeake. This one-bedroom flat provides complimentary kayak access for exploring the waterways, free parking, and a fully equipped kitchen, ideal for extended stays of 90 nights or more.
9.7 58 reviews
Chesapeake, VA
24/07 – 26/07
₹27826/nighttotal: ₹55652 (2 )
Cozy Cottage W/loft, Wifi, Workspace, Near Casino
1 4
apartment , Portsmouth
This apartment is situated in a peaceful neighbourhood, just a short distance from Portsmouth's attractions, offering a quiet retreat from the city centre. It has consistently received excellent ratings for location, cleanliness, and overall experience. This two-bedroom property comfortably accommodates up to five guests, featuring a loft-style master bedroom and a downstairs bedroom with a bunk bed. The apartment is well-equipped with amenities, including a fully-fitted kitchen, air conditioning, a private garden, and parking, ensuring a comfortable stay.
9.8 20 reviews
Chesapeake, VA
24/07 – 26/07
₹21812/nighttotal: ₹43624 (2 )
The Smarthouse Getaway!
1 4
apartment , Portsmouth
This newly renovated two-bedroom flat in Portsmouth is located in a well-connected district, offering convenient access to local attractions. This apartment, ideal for up to five guests, features modern amenities including air conditioning, a fully equipped kitchen with a fridge and microwave, smart televisions, smart outlets with USB ports, and remote-controlled lighting, with parking and a garden also available.
10 1 review
Chesapeake, VA
31/07 – 31/08
₹12087/nighttotal: ₹374697 (31 )
Traveling Professional Condo
1 2
apartment , Chesapeake
This Western Branch condo in Chesapeake offers a peaceful retreat, conveniently located near major cities including Norfolk, Newport News, Portsmouth, Suffolk, and Virginia Beach. The two-bedroom apartment sleeps four, features a fully equipped kitchen with stainless steel appliances, in-unit laundry, smart TVs, and assigned parking, providing comfortable accommodation for families or professionals visiting the area.
9.9 57 reviews
Chesapeake, VA
14/08 – 16/08
₹25249/nighttotal: ₹50498 (2 )
Stylish Two Bdrm, 1 1/2 Bth, King Bed Townhouse
1 2
apartment , Portsmouth
This two-bedroom apartment in Portsmouth is situated less than a mile from the new Rivers Casino, offering easy access to entertainment and dining options. The apartment has received excellent ratings for location, cleanliness, and overall user experience. The property can comfortably accommodate up to four guests and features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher. The apartment also benefits from air conditioning, a garden, and parking, ensuring a comfortable and convenient stay.
9.8 28 reviews
Chesapeake, VA
16/08 – 27/08
₹21487/nighttotal: ₹236357 (11 )
Cowbell Cottage
1 4
apartment , Chesapeake
Cowbell Cottage, a three-bedroom Chesapeake countryside retreat, is situated a short drive from Chesapeake city centre, offering easy access to local amenities. This self-catering property sleeps eight guests and boasts a kitchen, air conditioning, internet access, and pet-friendly accommodation.
9.9 22 reviews
Chesapeake, VA
23/06 – 25/06
₹22242/nighttotal: ₹44484 (2 )
The Couple’s $Pot @ The Dock Near Casino
1 3
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.
Chesapeake, VA
29/06 – 03/08
₹21434/nighttotal: ₹750190 (35 )
Large Home Perfect For Families & Traveling Crews
4 2
apartment , Chesapeake
This spacious flat is located in a residential district of Chesapeake, providing convenient access to local amenities and attractions. This four-bedroom flat accommodates up to eight guests and features a primary suite, a dedicated office, a well-equipped eat-in kitchen, a separate dining room, a garage with a washer and dryer, and a generous living room with a large sectional, all complemented by a large, fenced yard for outdoor enjoyment.
Chesapeake, VA
29/06 – 03/08
₹13766/nighttotal: ₹481810 (35 )
Cozy Studio Getaway
1 2
apartment , Portsmouth
This studio flat is located in the Port Norfolk subdivision of Portsmouth, offering a peaceful retreat. This accommodation allows pets and features a kitchenette, Wi-Fi, and air conditioning for up to three guests.
9.7 155 reviews
Chesapeake, VA
14/08 – 16/08
₹16896/nighttotal: ₹33792 (2 )
Penny’s Palace 1 Bed/1 Bath Home
1 2
apartment , Portsmouth
Penny's Palace, a bungalow in a quiet Portsmouth, Virginia neighbourhood, is conveniently located minutes from Olde Town Portsmouth and offers easy access to the Children's Museum of Virginia, Downtown Norfolk, and Virginia Beach (distances vary, but all are within a short driving distance – approximately 0-16km depending on the destination). This self-catering property sleeps two in a private suite with a fully equipped kitchen (including fridge, freezer, microwave, and dishwasher), a private bathroom, air conditioning, a garden, and on-site parking; guests also have access to a fitness centre and an outdoor seating area with a grill.
10 7 reviews
Chesapeake, VA
12/10 – 18/02
₹17125/nighttotal: ₹2209125 (129 )
Beautiful, Modern Furnished 3-bedroom, 2-bathroom Cottage Near Attractions.
3 2
apartment , Portsmouth
This Portsmouth cottage, situated 3.5km from Bon Secours Maryview Medical Center and 7.6km from Portsmouth Naval Hospital, offers easy access to major roads, shopping centres, and restaurants. The 111 square metre property comprises three bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen with appliances such as an Instant Pot and air fryer, plus on-site parking and in-unit laundry facilities.
9.6 45 reviews
Chesapeake, VA
25/09 – 30/09
₹23960/nighttotal: ₹119800 (5 )
Cozy Pool Home W/ Sun Porch!
1 4
apartment , Virginia Beach
This four-bedroom, two-bathroom apartment in Virginia Beach offers excellent guest ratings and is ideally situated for exploring the city's attractions, although the precise location and proximity to specific landmarks remain unspecified. Sleeping up to twelve guests, this spacious property boasts a fully equipped kitchen, swimming pool, garden, parking, and internet access, promising a comfortable stay with family-friendly amenities.
Best family friendly Chesapeake, VA Holiday Apartments and Self Catering Accommodations
Among the 568 accommodations in Chesapeake, VA, here are the 4 best family friendly holiday apartments
9.3 85 reviews
Chesapeake, VA
23/06 – 25/06
₹18758/nighttotal: ₹37516 (2 )
Comfortable Retreat W/ Backyard & Parking
2 3
apartment , Portsmouth
This two-bedroom duplex is situated just 500 metres from the Portsmouth Shipyard and a short drive from the city centre, offering easy access to attractions and amenities. The surrounding area is quiet and residential, providing a peaceful retreat after a day of exploring. The apartment comfortably sleeps six guests and features a well-equipped kitchen, a comfortable living area, and a modern bathroom. Guests can enjoy the convenience of air conditioning, free Wi-Fi, and parking, as well as the added benefit of being pet-friendly.
9.9 33 reviews
Chesapeake, VA
29/06 – 03/08
₹26428/nighttotal: ₹924980 (35 )
Beach Haven House
1 2
apartment , Virginia Beach
This family-friendly Virginia Beach house is centrally located near Town Center, approximately 24-32 km from Norfolk's attractions, the Chesapeake Bay, and the oceanfront beaches, and adjacent to a recreation centre with a gym and various sports facilities. The three-bedroom, two-bathroom property sleeps seven guests and boasts a full kitchen, swimming pool, garden with trampoline and fire pit, plus on-site mini-gym and free Wi-Fi.
10 1 review
Chesapeake, VA
31/07 – 31/08
₹16530/nighttotal: ₹512430 (31 )
Duplex W/fast Wi-fi & Stocked Kitchen
2 2
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.
9.6 4 reviews
Chesapeake, VA
12/10 – 18/02
₹13864/nighttotal: ₹1788456 (129 )
Sojourn's Spacious Apartment In Colley Manor
2 2
apartment , Norfolk
This Ghent flat in Norfolk is situated near Colley Avenue's restaurants and cafes, major hospitals (CHKD, EVMS, and Norfolk General), and offers easy access to public transport, including the Tide light rail to Norfolk city centre. The 84-square-metre (904-square-foot) two-bedroom, one-bathroom property sleeps four, includes a kitchen with a fridge, microwave, and dishwasher, and provides parking, air conditioning, internet access, and a contactless self check-in; a travel cot and high chair are available for an extra charge.
Best Chesapeake, VA holiday apartments with a balcony
8.0 9 reviews
Chesapeake, VA
14/08 – 16/08
₹43718/nighttotal: ₹87436 (2 )
4-bedroom House In Beautiful Virginia Beach Downtown
4 2
apartment , Virginia Beach
This four-bedroom property is located in the Northwest district of Virginia Beach, offering convenient access to the Waterside District and Greenbrier Mall, and is within 5 kilometres of First Landing State Park and Ocean Breeze Waterpark. This detached house accommodates up to ten guests, featuring three queen beds and one king bed, air conditioning, heating, and Wi-Fi, with essential amenities provided in the single bathroom.
8.3 33 reviews
Chesapeake, VA
25/09 – 30/09
₹14976/nighttotal: ₹74880 (5 )
Beautiful Queen Luxury Suite Near Downtown Norfolk
2 4
apartment , Norfolk
This Norfolk apartment is conveniently located just 12km from Topgolf Virginia Beach and 18km from Mount Trashmore Park, offering easy access to local attractions. The apartment has received excellent ratings for cleanliness and overall experience, with a good location rating. The 2-bedroom apartment, measuring 116 square metres, comfortably accommodates up to 4 guests. Enjoy a private garden, balcony, fireplace, and a fully equipped kitchen with a microwave, washing machine, free Wi-Fi, and parking on site.
Chesapeake, VA
25/09 – 30/09
₹30533/nighttotal: ₹152665 (5 )
Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood.
1 4
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.
10 1 review
Chesapeake, VA
25/09 – 30/09
₹27621/nighttotal: ₹138105 (5 )
Cambridge Knights A 3 Bedroom Home Full Of Charm
3 4
apartment , Portsmouth
This Portsmouth holiday home is located just 3km from attractions like the Emanuel AME Church, Commodore Theatre, and the Virginia Sports Hall of Fame and Museum, making it a great base for exploring the city. The surrounding area is quiet and residential, offering a peaceful escape from the hustle and bustle of the city centre. The property has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It features a fully equipped kitchen, a terrace or balcony, a spa, and free parking, as well as modern amenities like Wi-Fi and air conditioning.
Frequently asked questions about apartment rentals in Chesapeake, VA
What makes Chesapeake, VA unique or famous?
Chesapeake is known for its beautiful waterfront, with access to the Chesapeake Bay and its tributaries. It's also a city with a rich history, having played a significant role in the American Revolution.
Where can you find the best local markets and street food in Chesapeake, VA?
The Chesapeake Farmers Market, held on Saturdays at the Chesapeake City Park, is a great place to find local produce and crafts. For street food, the food trucks at the Greenbrier Mall food court offer a variety of options.
How is the public transportation system in Chesapeake, VA?
Chesapeake has a public transportation system called Hampton Roads Transit (HRT), offering bus services throughout the city. However, for getting around the wider area, you'll likely need a car.
Which seasonal events or festivals should apartment renters look forward to in Chesapeake, VA?
The Chesapeake Bay Wine Festival in the spring is a popular event, showcasing local wineries. The Chesapeake Bay Seafood Festival in the autumn celebrates the region's seafood bounty.
What amenities are typically included in apartments in Chesapeake, VA?
Most apartments in Chesapeake include central air conditioning, a washer and dryer, and a dishwasher. Some newer buildings may offer additional amenities like a fitness center or a swimming pool.
What leisure activities are available for relaxation in Chesapeake, VA?
Chesapeake offers plenty of opportunities for relaxation. You can enjoy the beaches at Chesapeake Bay, go for a walk or bike ride along the Chesapeake Bay Trail, or simply relax at one of the many parks in the city.
Destinations nearby
Best Chesapeake, VA holiday apartments with parking
10 2 reviews
Chesapeake, VA
31/07 – 31/08
₹13609/nighttotal: ₹421879 (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
31/07 – 31/08
₹20699/nighttotal: ₹641669 (31 )
Walk To River & Downtown: Portsmouth Apartment!
2 2
apartment , Portsmouth
This Portsmouth apartment, near the Children's Museum of Virginia (a 0.9km walk) and the Portsmouth Naval Shipyard Museum (a 1.1km walk), offers convenient access to local attractions. The 111-square-metre property comprises three bedrooms, one bathroom, and on-site parking, plus in-unit amenities including a washer/dryer, full kitchen, and air conditioning; BBQ facilities are also available.
10 1 review
Chesapeake, VA
31/07 – 31/08
₹18030/nighttotal: ₹558930 (31 )
Charming 2-bedroom House In Fabulous Portsmouth With Wifi, Ac
2 2
apartment , Portsmouth
This Portsmouth holiday home is conveniently located near the Waterside District and Greenbrier Mall, offering easy access to the Children's Museum of Virginia and the Portsmouth Naval Shipyard Museum. Sleeping up to five guests, this two-bedroom, two-bathroom property boasts a queen bed, a double bed, a single bed, WiFi, a washing machine and iron, and is ideal for families exploring Portsmouth’s attractions.
9.8 51 reviews
Chesapeake, VA
23/06 – 25/06
₹16276/nighttotal: ₹32552 (2 )
Virginia Beach, Getaway
1 3
apartment , Virginia Beach
This modern one-bedroom apartment in Virginia Beach is situated on a quiet cul-de-sac, minutes from Lynnhaven Inlet, local shops, restaurants, and beaches, as well as the Virginia Beach Convention Center and sports facilities. The self-catering flat offers two queen-size beds sleeping up to four guests, a fully equipped kitchen, in-unit laundry, and a newly fitted bathroom; enjoy easy access to the area's attractions.
Best Chesapeake, VA holiday apartments with air conditioning
10 3 reviews
Chesapeake, VA
19/07 – 18/10
₹23042/nighttotal: ₹2096822 (91 )
3br Gem Near Rivers Casino Comfort & Convenience
3 1
apartment , Portsmouth
This Portsmouth holiday home, ideally situated for exploring the city, offers easy access to Norfolk and Virginia Beach, and is conveniently located near the Waterside District and Greenbrier Mall shopping centres; distances to these attractions are not specified. Sleeping six guests, this three-bedroom, one-bathroom apartment boasts a fully remodelled modern interior, including a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, a garden, parking, and Wi-Fi; five beds provide ample sleeping space.
9.4 313 reviews
Chesapeake, VA
23/06 – 25/06
₹16180/nighttotal: ₹32360 (2 )
Olde Towne 4 Bedroom -2200 Sq Ft
1 3
apartment , Portsmouth
This Portsmouth apartment is located just a few hundred metres from the Strawbery Banke Museum and a 1 kilometre walk from Market Square, offering easy access to the city's historic district and attractions. The apartment has received excellent user ratings for its location, cleanliness, and overall experience. This two-unit property provides ample space for larger groups or families, with each unit containing two bedrooms and a bathroom. Guests can enjoy a range of amenities, including fully equipped kitchens, in-unit laundry facilities, smart locks, WiFi, TVs, and comfortable bedding.
9.7 66 reviews
Chesapeake, VA
25/09 – 30/09
₹20123/nighttotal: ₹100615 (5 )
Near Casino, Va Beach, Large Yard, Quite Relaxing
1 4
apartment , Portsmouth
This Portsmouth apartment is conveniently located just 5.6 kilometres from the Norfolk Waterside District, 3.2 kilometres from Roger Browns and 5.6 kilometres from Rivers Casino, all while being situated in a peaceful neighbourhood. The apartment has received excellent ratings for location, cleanliness, and user experience. The property features two separate suites, offering ample space for up to 7 guests. Amenities include a fully equipped kitchen, laundry facilities, a garden with patio furniture, a fitness centre and secure access with a keypad.
Chesapeake, VA
31/07 – 31/08
₹19024/nighttotal: ₹589744 (31 )
Central Chesapeake Stay| Near Mall, Trails & Parks
1 2
apartment , Chesapeake
This Chesapeake flat is located in a peaceful residential area, offering convenient access to shops, eateries, parks, and major roads for exploring Chesapeake, Virginia Beach, and the wider Hampton Roads region. This accommodating residence welcomes pets and features air conditioning, a kitchen, and internet, with capacity for 10 guests across its layout, providing a comfortable, home-like experience near amenities and recreational spaces.