Best apartment offers in Chesapeake, VA

568 available apartment offers

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

568 Holiday apartments Chesapeake, VA

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

Trycam’s Humble Abode - Chesapeake, VA
9.2 44 reviews
Chesapeake, VA
16/08 – 27/08
SG$254/nighttotal: SG$2794 (11 )

Trycam’s Humble Abode

1 4
apartment , Chesapeake
This Chesapeake property is conveniently located just a short drive from Virginia Beach, Busch Gardens, and the Virginia Aquarium, making it ideal for exploring the region's attractions. The accommodation has received excellent ratings for cleanliness and user experience, while its location has been rated very good.
This three-bedroom house can comfortably accommodate up to eight guests, with queen-sized beds in each bedroom and a queen-sized sofa bed downstairs. The house is well-equipped with a full kitchen, including a dishwasher, microwave, and other appliances, as well as a private outdoor space and parking.
Comfortable Retreat W/ Backyard & Parking - Chesapeake, VA
10 1 review
Chesapeake, VA
12/10 – 18/02
SG$232/nighttotal: SG$29928 (129 )

Comfortable Retreat W/ Backyard & Parking

2 2
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.
Riverfront Portsmouth Home Near Casino & Patio - Chesapeake, VA
9.7 32 reviews
Chesapeake, VA
16/08 – 27/08
SG$392/nighttotal: SG$4312 (11 )

Riverfront Portsmouth Home Near Casino & Patio

1 4
apartment , Portsmouth
This Portsmouth waterfront house, located approximately 1.3 km from the Rivers Casino and 0.8 km from Historic Old Towne, offers stunning Elizabeth River views and private patio access.
Sleeping up to 10 guests, this three-bedroom, two-and-a-half-bathroom property boasts a fully equipped kitchen, high-speed Wi-Fi, and family-friendly amenities including a travel cot and high chair; nearby attractions include the Portsmouth Waterfront.
Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
10 1 review
Chesapeake, VA
12/10 – 18/02
SG$231/nighttotal: SG$29799 (129 )

Cheerful 2 Bedroom Home Near Virginia Wesleyan

2 2
apartment , Virginia Beach
This Northwest Virginia Beach holiday home is situated 0.5km from Virginia Wesleyan University, within 5km of Cypress Point Country Club, and less than 5km from Norfolk Premium Outlets.
This 89 square metre property offers two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen with oven and microwave, a private balcony, on-site barbecue grills, and in-unit laundry facilities.

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
SG$344/nighttotal: SG$3784 (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.
Spacious Modern 3-bedroom House In Beautiful Portsmouth City. - Chesapeake, VA
Chesapeake, VA
08/07 – 13/07
SG$786/nighttotal: SG$3930 (5 )

Spacious Modern 3-bedroom House In Beautiful Portsmouth City.

3 5
apartment , Portsmouth
This four-bedroom, three-bathroom flat in Portsmouth is conveniently located 5.6 kilometres from Town Point Park and 16.1 kilometres from Chesapeake Bay, with the Children's Museum of Virginia and Portsmouth Naval Shipyard Museum a mere 2.4 kilometres away.
Guests can enjoy complimentary Wi-Fi, air conditioning, and on-site laundry facilities in this accommodation, which also features a sunroom or lanai and offers parking for up to six people.
Monthly, Dog-friendly Home At Orange Blossom - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
SG$257/nighttotal: SG$33153 (129 )

Monthly, Dog-friendly Home At Orange Blossom

3 2
apartment , Virginia Beach
This three-bedroom, four-bathroom apartment is situated in Virginia Beach's Green Run neighbourhood, approximately 24 kilometres from various beaches and close to Norfolk.
The self-catering property offers a spacious open-plan layout, sleeping up to five guests, and boasts a fully fenced backyard, on-site parking, and a fully equipped kitchen including a dishwasher; nearby attractions include Lynnhaven Mall, Landstown Commons, Town Centre, and Mount Trashmore Park.
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews
Chesapeake, VA
23/06 – 25/06
SG$480/nighttotal: SG$960 (2 )

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

4 3
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 Bay Maritime Museum is a great place to learn about the region's maritime history. You could also visit the Great Bridge Battlefield and National Monument, which commemorates a key battle in the American Revolution.
  • 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 and 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.

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

    Chesapeake has a public bus system, Hampton Roads Transit (HRT), which provides service throughout the city. However, it's important to note that it's not as extensive as in larger cities, and you might need to rely on a car for some trips.
  • 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.

  • 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 year in the fall. You might also enjoy the Chesapeake Arts Festival, which takes place in the summer and features live music, art exhibits, and food vendors.
  • What are the best apartments for families and kids in Chesapeake, VA?

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

    Apartments in Chesapeake typically include basic amenities like central air conditioning, a refrigerator, a stove, and a dishwasher. Some newer apartments might also have in-unit laundry facilities, a balcony, and a parking space.
  • What are the best pet friendly apartments in Chesapeake, VA?

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

    Chesapeake offers a variety of leisure activities, including walking or cycling along the Chesapeake Bay Trail, visiting the Chesapeake Arboretum, or enjoying a round of golf at one of the many golf courses in the city.
  • What are the best apartments with parking in Chesapeake, VA?

Destinations nearby

Best Chesapeake, VA holiday apartments with parking

Cozy Studio Getaway - Chesapeake, VA
Chesapeake, VA
29/06 – 03/08
SG$185/nighttotal: SG$6475 (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.
Enticing Den With Backyard And Indoor Fireplace - Chesapeake, VA
Chesapeake, VA
31/07 – 31/08
SG$163/nighttotal: SG$5053 (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.
Cozy Cottage W/loft, Wifi, Workspace, Near Casino - Chesapeake, VA
9.7 58 reviews
Chesapeake, VA
24/07 – 26/07
SG$375/nighttotal: SG$750 (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.
Charming 2 Bedroom, 2 Bath Townhome Located In Portsmouth, Simple And Elegant!! - Chesapeake, VA
9.2 28 reviews
Chesapeake, VA
24/07 – 26/07
SG$484/nighttotal: SG$968 (2 )

Charming 2 Bedroom, 2 Bath Townhome Located In Portsmouth, Simple And Elegant!!

2 4
apartment , Portsmouth
This Portsmouth townhouse, centrally located in Hampton Roads, offers easy access to the Rivers Casino (distance unspecified) and Virginia Beach Boardwalk (driving distance unspecified).
The 84-square-metre (904 sq ft) property sleeps four guests in two bedrooms with queen-size beds and smart TVs, and includes a fully equipped kitchen, private garden, parking, and excellent Wi-Fi.

Best Chesapeake, VA holiday apartments with air conditioning

Home Away From Home! Townhome - Chesapeake, VA
8.0 1 review
Chesapeake, VA
29/06 – 03/08
SG$228/nighttotal: SG$7980 (35 )

Home Away From Home! Townhome

1 2
apartment , Chesapeake
This Chesapeake townhome is ideally situated in Greenbrier, offering easy walking access to local parks, a lake, shops, restaurants, and theatres.
The two-bedroom, two-bathroom property sleeps four guests, features a fully equipped kitchen with dishwasher, in-unit laundry, multiple Roku TVs, and a designated workspace; enjoy nearby outdoor recreation opportunities.
The Mermaids Lair ‍️ - Chesapeake, VA
9.0 13 reviews
Chesapeake, VA
14/08 – 16/08
SG$333/nighttotal: SG$666 (2 )

The Mermaids Lair ‍️

1 2
apartment , Portsmouth
This Portsmouth waterfront apartment offers stunning Crystal Lake views and private dock access, situated approximately 16km from Norfolk's attractions, 32km from Norfolk Naval Base, and 40km from Virginia Beach.
The self-catering studio, sleeping two guests, features a kitchenette with microwave and fridge, a custom shower, a shared fire pit, and automatic gate access for enhanced security.
3 Bdr | 2 Bh Townhouse In Vb - Chesapeake, VA
Chesapeake, VA
08/07 – 13/07
SG$461/nighttotal: SG$2305 (5 )

3 Bdr | 2 Bh Townhouse In Vb

1 5
apartment , Virginia Beach
This Virginia Beach townhouse is located in a quiet, convenient area, approximately 1.6 kilometres from Lake Edwards, offering easy access to the city's beaches, dining, and shopping.
This two-storey dwelling accommodates up to six guests, featuring a fully equipped kitchen, air conditioning, internet, and a dedicated workspace, with pets welcome.
Cozy 4 Bed 2 Bath Home - Norfolk, Centrally Located - Chesapeake, VA
9.6 4 reviews
Chesapeake, VA
12/10 – 18/02
SG$230/nighttotal: SG$29670 (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.
©2026 cozycozy.com