Best apartment offers in Chesapeake, VA

568 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Chesapeake, VA apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

568 Holiday apartments in Chesapeake, VA

Best family friendly Chesapeake, VA Holiday Apartments

Among the 568 accommodations in Chesapeake, VA, here are the 4 best family friendly holiday apartments

3br, 6 Beds  Prime Stay Near Rivers Casino! - Chesapeake, VA
10 1 review
Chesapeake, VA
31/07 – 31/08
A$393/nighttotal: A$12183 (31 )

3br, 6 Beds Prime Stay Near Rivers Casino!

3 2
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.
Cozy Quarters Near Nmcp - Chesapeake, VA
Chesapeake, VA
31/07 – 31/08
A$148/nighttotal: A$4588 (31 )

Cozy Quarters Near Nmcp

1 2
apartment , Portsmouth
This two-bedroom duplex flat is situated in Portsmouth, a short distance from the Naval Medical Center and surrounding shipyards, making it an ideal base for professionals working in the area.
This family-friendly accommodation offers a garden, air conditioning, and a kitchen equipped with a fridge and microwave, providing comfort for up to four guests with one bathroom.
Spacious Chesapeake Home W/ Pool Table! - Chesapeake, VA
9.0 55 reviews
Chesapeake, VA
08/07 – 13/07
A$545/nighttotal: A$2725 (5 )

Spacious Chesapeake Home W/ Pool Table!

4 5
apartment , Chesapeake
This Chesapeake apartment is conveniently located just a few kilometres from the Elizabeth River, offering easy access to the Chesapeake Square Mall, Portsmouth City Park, the Chesapeake Arboretum, and the Chrysler Museum of Art. It has received excellent ratings for user experience, location, and cleanliness.
The property has four bedrooms and three bathrooms, comfortably accommodating up to eight guests. It includes a fully equipped kitchen, in-unit laundry, free WiFi, central air conditioning and heating, a private yard, a deck, a fireplace, a games room with a pool table, and Smart TVs.
Cook's Country Escape - Cozy Retreat - Chesapeake, VA
9.9 134 reviews
Chesapeake, VA
25/09 – 30/09
A$274/nighttotal: A$1370 (5 )

Cook's Country Escape - Cozy Retreat

1 4
apartment , Chesapeake
This countryside home is located in Chesapeake, Virginia, just 1.6 kilometres from Ballahack Airsoft Field, Triple R Ranch, and the Northwest Naval Annex and Navy Exchange, offering a peaceful escape from city life. The property has received excellent ratings for its cleanliness, location, and overall user experience.
The apartment has three bedrooms and one bathroom, comfortably accommodating up to eight guests. It features a fully equipped kitchen, a large backyard with a playground and picnic area, a covered deck with a fire pit, and modern amenities like a washer and dryer, a Keurig coffee maker, and a propane fireplace.

Best Chesapeake, VA holiday apartments with a balcony

Cambridge Knights A 3 Bedroom Home Full Of Charm - Chesapeake, VA
10 1 review
Chesapeake, VA
16/08 – 27/08
A$381/nighttotal: A$4191 (11 )

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
A$264/nighttotal: A$1320 (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.
4-bedroom House In Beautiful Virginia Beach Downtown - Chesapeake, VA
8.0 9 reviews
Chesapeake, VA
14/08 – 16/08
A$651/nighttotal: A$1302 (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.
Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood. - Chesapeake, VA
Chesapeake, VA
25/09 – 30/09
A$455/nighttotal: A$2275 (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.

Frequently asked questions about apartment rentals in Chesapeake, VA

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

    The Chesapeake Historical Society Museum is a great place to learn about the city's rich history. The South Norfolk Jordan Branch Railroad Museum is another great option, with a collection of historic locomotives and rolling stock. The Chesapeake Bay Maritime Museum in nearby St. Michaels, Maryland is also worth a visit. It's a bit of a drive, but it's a great place to learn about the history of the Chesapeake Bay.
  • 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 shoreline along the Chesapeake Bay. It's also home to a large number of parks and green spaces, making it a great place to enjoy the outdoors. The city is also home to a diverse population, with a rich history and culture.
  • What are the best apartments with a pool in Chesapeake, VA?

    Beautiful And Chic Studio Apartment, Cheshire Retreat and Artist's Retreat 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 is a great place to find fresh produce, local crafts, and delicious food. It's held every Saturday from May to October at the Chesapeake City Park. There are also several food trucks that can be found around the city, particularly in the Greenbrier area.
  • 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 operates throughout the city and connects to other cities in the Hampton Roads area. It's not as extensive as the system in a larger city, but it can be a convenient and affordable way to get around. If you're planning on exploring the city, it's best to rent a car.
  • 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 is a popular event held every October. The Chesapeake Arts Festival is another highlight, featuring local artists and musicians. The Chesapeake Bay Seafood Festival is a great way to sample fresh seafood and enjoy live music.
  • What are the best pet friendly apartments in Chesapeake, VA?

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

    Most apartments in Chesapeake include central air conditioning, a refrigerator, stove, and oven. Some apartments also have a dishwasher, washer, and dryer. The availability of these amenities will vary depending on the specific apartment complex.
  • What are the best apartments with parking in Chesapeake, VA?

Destinations nearby

Best Chesapeake, VA holiday apartments with parking

Spacious Chesapeake Home W/ Pool Table! - Chesapeake, VA
9.0 12 reviews
Chesapeake, VA
16/08 – 27/08
A$477/nighttotal: A$5247 (11 )

Spacious Chesapeake Home W/ Pool Table!

4 4
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.
The Point! Private Waterfront  Oasis! - Chesapeake, VA
9.9 129 reviews
Chesapeake, VA
08/07 – 13/07
A$1304/nighttotal: A$6520 (5 )

The Point! Private Waterfront Oasis!

1 5
apartment , Norfolk
This Norfolk holiday home, ideally situated near Virginia Beach, offers easy access to Oceanview Beach and attractions such as Rivers Casino and the Waterside District, with distances to these locations needing clarification.
Sleeping up to 10 guests in four bedrooms and two bathrooms, this self-catering property boasts a fully equipped kitchen, air conditioning, a garden, fitness centre, parking, and excellent guest reviews, promising a comfortable stay.
Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth - Chesapeake, VA
9.6 4 reviews
Chesapeake, VA
14/08 – 16/08
A$325/nighttotal: A$650 (2 )

Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth

1 2
apartment , Portsmouth
This one-bedroom flat in Portsmouth is situated a 19-minute drive from Town Point Park and 40 minutes from Chesapeake Bay, offering convenient access to the Chrysler Museum of Art and the Children's Museum of Virginia.
This pet-friendly apartment accommodates up to three guests and includes on-site parking, complimentary Wi-Fi, air conditioning, and essential amenities such as towels, linens, and soap, with a check-out time of 12:00.
Downtown Norfolk Loft - Chesapeake, VA
9.7 104 reviews
Chesapeake, VA
31/07 – 31/08
A$214/nighttotal: A$6634 (31 )

Downtown Norfolk Loft

1 2
apartment , Norfolk
The Downtown Norfolk Loft apartment is located in the city centre, just 11.6 kilometres from Topgolf Virginia Beach, 17.7 kilometres from Mount Trashmore Park and 25.7 kilometres from Virginia Beach National Golf Club. This one-bedroom apartment has received excellent ratings for its location, cleanliness and overall experience.
This comfortable flat is 98 square metres and can accommodate up to two guests. It comes with a fully equipped kitchen, air conditioning, free Wi-Fi and parking, making it ideal for a relaxing stay in Norfolk.

Best Chesapeake, VA holiday apartments with air conditioning

Condo Near Portsmouth Naval On Webster Avenue - Chesapeake, VA
10 20 reviews
Chesapeake, VA
19/07 – 18/10
A$196/nighttotal: A$17836 (91 )

Condo Near Portsmouth Naval On Webster Avenue

1 1
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.
Beautiful 3 Bedroom Apt In Historic Parkview - Chesapeake, VA
9.1 124 reviews
Chesapeake, VA
29/06 – 03/08
A$227/nighttotal: A$7945 (35 )

Beautiful 3 Bedroom Apt In Historic Parkview

1 2
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.
New Casino Nearby! King Bed, Two Bdrm, 1 1/2 Bth - Chesapeake, VA
9.7 75 reviews
Chesapeake, VA
24/07 – 26/07
A$409/nighttotal: A$818 (2 )

New Casino Nearby! King Bed, Two Bdrm, 1 1/2 Bth

1 4
apartment , Portsmouth
This two-bedroom apartment is conveniently located in a central Portsmouth district, within a mile of the Rivers Casino and close to shopping centres like Kroger, TJ Maxx, and Walmart. It has received excellent ratings for its location, cleanliness, and overall user experience.
The apartment can accommodate up to four guests and features a king-size bed in the master bedroom and a queen-size bed in the second bedroom. Amenities include a fully equipped kitchen, a private patio, a washer and dryer, air conditioning, a Jacuzzi, and parking.
Best Location In Olde Towne Portsmouth - Chesapeake, VA
9.9 129 reviews
Chesapeake, VA
31/07 – 31/08
A$109/nighttotal: A$3379 (31 )

Best Location In Olde Towne Portsmouth

1 2
apartment , Portsmouth
This charming flat is situated in the historic Old Towne district of Portsmouth, Virginia, just a short walk from the Naval Medical Center and the ferry terminal to downtown Norfolk. It has received excellent ratings for its location, cleanliness and overall experience.
The apartment has one bedroom and one bathroom, comfortably accommodating two guests. It features a well-equipped kitchen, a private patio, central heating and air conditioning, a TV with basic cable, and Wi-Fi access.
©2026 cozycozy.com