Best apartment offers in Chesapeake, VA

568 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Chesapeake, VA apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

568 Best apartments in Chesapeake, VA

Guest-Favourite Holiday Apartments for Families in Chesapeake, VA

Kid-friendly holiday apartments in Chesapeake, VA provide easy access to city attractions, ensuring a smoother trip where everyone stays comfortable.

Gorgeous Olde Towne Historic Home - Modern Updates - Chesapeake, VA
10 196 reviews
Chesapeake, VA
25/09 – 30/09
£200/nighttotal: £1000 (5 )

Gorgeous Olde Towne Historic Home - Modern Updates

3 4
apartment , Portsmouth
This charming 1880s home is located in Olde Towne Portsmouth, just 1 kilometre from the Elizabeth River harbour, a 3-minute walk from the ferry to Norfolk's downtown and a 5-minute walk to High Street with its shops, restaurants, and cultural attractions. The property has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The house has three bedrooms and two bathrooms, accommodating up to seven guests. It offers a range of modern amenities, including a fully equipped kitchen, air conditioning, a private garden, parking, and free internet access, as well as unique historic features like original pinewood floors, windows, doors, and antique doorknobs.
The Chesapeake Gray\n\nhistorical Waterside District\n20 Mins To Oceanfront - Chesapeake, VA
9.6 4 reviews
Chesapeake, VA
25/09 – 30/09
£348/nighttotal: £1740 (5 )

The Chesapeake Gray\n\nhistorical Waterside District\n20 Mins To Oceanfront

3 4
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.
Spacious Chesapeake Home W/ Pool Table! - Chesapeake, VA
9.0 12 reviews
Chesapeake, VA
23/06 – 25/06
£376/nighttotal: £752 (2 )

Spacious Chesapeake Home W/ Pool Table!

4 3
apartment , Chesapeake
This 4-bedroom Chesapeake holiday home is situated in Western Branch North, just a short distance from Chesapeake Square Mall and a drive from Portsmouth City Park and the Chesapeake Arboretum. It has received very good ratings from previous guests.
The property offers 223 square metres of space, accommodating up to 8 guests, with 4 bedrooms and 3 bathrooms. It features a range of amenities, including a private yard, a deck, a pool table, a jetted tub, smart TVs, a fireplace, a washer and dryer, and free Wi-Fi.
Retreat Away From Home - Chesapeake, VA
9.8 19 reviews
Chesapeake, VA
09/07 – 14/07
£234/nighttotal: £1170 (5 )

Retreat Away From Home

1 5
apartment , Portsmouth
This Portsmouth house rental is peacefully situated near the water, a short ferry ride from the Waterside District, shopping, and the Tides baseball games, and within easy reach of Portsmouth city centre.
Sleeping up to ten guests, this three-bedroom property boasts a fully equipped kitchen, dedicated office space, driveway parking, and exclusive use of the downstairs, offering ample space and privacy.

Discover Self-Catering Apartments with a Terrace in Chesapeake, VA

Watching the sunset over the city skyline from your own private balcony is a premium detail that elevates any trip to Chesapeake, VA.

Cambridge Knights A 3 Bedroom Home Full Of Charm - Chesapeake, VA
10 1 review
Chesapeake, VA
25/09 – 30/09
£216/nighttotal: £1080 (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.
Historic Old Towne Southern Charm - Chesapeake, VA
9.6 35 reviews
Chesapeake, VA
25/09 – 30/09
£138/nighttotal: £690 (5 )

Historic Old Towne Southern Charm

2 4
apartment , Portsmouth
This charming 2-bedroom flat is located in Old Towne Portsmouth, just a short walk from the city's restaurants, shops, and attractions. The area is known for its historic architecture and lively atmosphere, making it a great base for exploring the city. The apartment has a very good user rating, indicating a positive experience for previous guests.
This spacious home can comfortably accommodate up to 7 guests. It features a well-equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a terrace, and a garden. Guests can also enjoy free Wi-Fi and the convenience of a washing machine and dryer.
Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood. - Chesapeake, VA
Chesapeake, VA
25/09 – 30/09
£239/nighttotal: £1195 (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.
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews
Chesapeake, VA
29/06 – 03/08
£192/nighttotal: £6720 (35 )

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

4 2
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.

Frequently asked questions about apartment rentals in Chesapeake, VA

  • What are the top cultural and historical sites in Chesapeake, VA?

    The Chesapeake City Park is home to the Chesapeake Museum and Cultural Center, which has exhibits about the city's history and culture. The Great Dismal Swamp National Wildlife Refuge is a great place to learn about the natural history of the area.
  • What are the best apartments in Chesapeake, VA?

  • What makes Chesapeake, VA unique or famous?

    Chesapeake is known for its beautiful waterfront, with miles of coastline along the Chesapeake Bay. It's also home to a large military presence, with Naval Station Norfolk and Joint Expeditionary Base Little Creek-Fort Story nearby.
  • What are the best apartments with a pool in Chesapeake, VA?

  • Where can you find the best local markets and street food in Chesapeake, VA?

    The Chesapeake Farmers Market, held every Saturday from April to October, is a great place to find local produce, baked goods, and crafts. For street food, try the food trucks that gather at the Chesapeake Town Center on Fridays.
  • What are the best apartments with a jacuzzi in Chesapeake, VA?

    The best apartments with a jacuzzi in Chesapeake, VA are Rock Star Mansion, Peace On The Lake and Gorgeous 1 Bedroom With Free Wifi & Street Parking.

  • How is the public transportation system in Chesapeake, VA?

    Chesapeake has a public bus system, Hampton Roads Transit, which connects to other parts of the Hampton Roads region. However, it's generally recommended to have a car for getting around the city.
  • What are the best apartments for families and kids in Chesapeake, VA?

  • Which seasonal events or festivals should apartment renters look forward to in Chesapeake, VA?

    The Chesapeake Bay Wine Festival in October is a popular event, featuring wine tastings and live music. The Chesapeake Arts Festival in May is a great way to enjoy local art, music, and food.
  • What are the best pet friendly apartments in Chesapeake, VA?

  • What amenities are typically included in apartments in Chesapeake, VA?

    Most apartments in Chesapeake come with central air conditioning, a refrigerator, and a stove. Some may also have a dishwasher, washer, and dryer. Be sure to check the specifics of each apartment.
  • What are the best apartments with parking in Chesapeake, VA?

  • What leisure activities are available for relaxation in Chesapeake, VA?

    For relaxation, Chesapeake has several parks with walking trails, such as the Chesapeake Arboretum and the Northwest River Park. You can also enjoy a day at the beach at Chesapeake Bay.

Destinations nearby

Explore Self-Catering Apartments with Free Parking in Chesapeake, VA

Free on-site parking comes with these apartments, letting you focus on the Chesapeake, VA city centre from the moment you arrive.

Comfortable Retreat W/ Backyard & Parking - Chesapeake, VA
10 1 review
Chesapeake, VA
02/07 – 05/07
£267/nighttotal: £801 (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.
Enticing Den With Backyard And Indoor Fireplace - Chesapeake, VA
Chesapeake, VA
31/07 – 31/08
£95/nighttotal: £2945 (31 )

Enticing Den With Backyard And Indoor Fireplace

2 2
apartment , Virginia Beach
This Virginia Beach holiday home is situated near Lynnhaven Mall, Virginia Beach Sportsplex, and Mount Trashmore Park, all within 5 kilometres, with the Veterans United Home Loans Amphitheatre and Princess Anne Plaza Shopping Centre within 10 kilometres.
This 81-square-metre property sleeps four guests in two bedrooms and one bathroom, boasting a fully equipped kitchen, Jacuzzi, private fenced garden, free Wi-Fi, and a fireplace; nearby attractions include Lynnhaven Mall, Mount Trashmore Park, and the Virginia Beach Sportsplex.
Sojourn 2 Bedroom Townhouse In Virginia Beach - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
£114/nighttotal: £14706 (129 )

Sojourn 2 Bedroom Townhouse In Virginia Beach

2 2
apartment , Virginia Beach
This Northwest Virginia Beach townhouse, located on a corner lot, offers 87 square metres of living space and convenient highway access for exploring Norfolk and Chesapeake, with First Landing State Park and the Virginia Aquarium within 5 kilometres.
This family-friendly dwelling accommodates up to five guests with two bedrooms, one bathroom, a fully equipped kitchen featuring granite countertops, and entertainment options including Hulu Live and Netflix, alongside high-speed Wi-Fi.
Country House Is Perfect For Remote Work Location - Chesapeake, VA
10 4 reviews
Chesapeake, VA
31/07 – 31/08
£101/nighttotal: £3131 (31 )

Country House Is Perfect For Remote Work Location

2 2
apartment , Virginia Beach
This two-bedroom apartment is located in the Tri-city area of Virginia Beach, Chesapeake, and Norfolk, just 5 kilometres from Sentara Hospital at Princess Anne and the Virginia Beach Municipal Center. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment features a spacious backyard and a furnished deck, perfect for relaxing or hosting small gatherings. Guests have access to the entire home, including a small garage, and can enjoy amenities such as air conditioning, a fully equipped kitchen, and dedicated workspaces in each bedroom.

Best Chesapeake, VA holiday apartments with air conditioning

Waterfront Portsmouth Home  Dock Access - Chesapeake, VA
9.6 4 reviews
Chesapeake, VA
09/07 – 14/07
£383/nighttotal: £1915 (5 )

Waterfront Portsmouth Home Dock Access

3 5
apartment , Portsmouth
This waterfront property is located in Portsmouth, just a short distance from the Waterside Festival Marketplace and Greenbrier Mall, offering easy access to shopping and entertainment. The apartment is also close to the Norfolk Scope and Ted Constant Convocation Center, ideal for those looking to attend events or games.
This spacious apartment can comfortably accommodate up to six guests and features three bedrooms and two bathrooms. Guests can enjoy the stunning views of Hull Creek/Elizabeth River from the terrace or balcony, and relax in the garden or on the dock. The apartment also offers a range of amenities, including a fully equipped kitchen, air conditioning, parking, and internet access.
Condo Near Portsmouth Naval On Webster Avenue - Chesapeake, VA
10 20 reviews
Chesapeake, VA
24/07 – 26/07
£239/nighttotal: £478 (2 )

Condo Near Portsmouth Naval On Webster Avenue

1 4
apartment , Portsmouth
This Portsmouth apartment, ideal for families or groups of up to six, is situated less than 1.6km from Portsmouth Naval Hospital and 8km from the Rivers Casino.
The three-bedroom, one-bathroom flat offers free internet, air conditioning, parking, and a fully equipped kitchen; enjoy easy access to local attractions and a peaceful atmosphere.
Traveling Professional Condo - Chesapeake, VA
10 1 review
Chesapeake, VA
31/07 – 31/08
£94/nighttotal: £2914 (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.
Free Breakfast. Indoor Pool & Hot Tub. Close To The Virginia Beach Business District! - Chesapeake, VA
8.0 4 reviews
Chesapeake, VA
27/06 – 04/07
£198/nighttotal: £1386 (7 )

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

1 2
apartment , Chesapeake
This Chesapeake City seaside apartment is situated 0.8km from the Chesapeake Conference Centre, 4.8km from Greenbrier Mall, and 4.8km from Chesapeake City Park.
This one-bedroom, one-bathroom flat sleeps six guests and boasts an indoor pool, hot tub, complimentary breakfast, and a fully equipped kitchen including a fridge, microwave, and dishwasher; free Wi-Fi and limited housekeeping are also provided.
©2026 cozycozy.com