Best apartment offers in Chesapeake, VA

790 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

790 Holiday apartments Chesapeake, VA

Best family friendly Chesapeake, VA Holiday Apartments and Self Catering Accommodations

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

Hidden Gem A Comfortable 4bedroom Home With A Fenced-in Yard. - Chesapeake, VA
10 10 reviews

Hidden Gem A Comfortable 4bedroom Home With A Fenced-in Yard.

apartment, Portsmouth
This Portsmouth holiday home is situated within 5km of Portsmouth City Park, Chesapeake Square Mall, and Rivers Casino Portsmouth, offering easy access to local amenities and attractions.
The 160 square metre property boasts four bedrooms, two bathrooms, sleeping up to eight guests, and features a fully equipped kitchen, garden, patio, free Wi-Fi, and parking.
Historic Private Guest Apartment - Chesapeake, VA
10 12 reviews

Historic Private Guest Apartment

apartment, Norfolk
This private apartment, located in Norfolk's West Freemason district, offers easy walking access to the riverfront, local shops, and dining establishments, with the Children's Museum of Virginia and Lamberts Point Golf Course approximately 3 kilometres away.
This family-friendly flat accommodates up to four guests and features two bedrooms, one bathroom, air conditioning, a fully equipped kitchen with a fridge, microwave, and dishwasher, a separate living area, and an in-unit washer and dryer.
Cozy Ranch Home, Centrally Located Near Chicks Beach! - Chesapeake, VA
8.6 9 reviews

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.
5 Minutes To The Casino!family Sized Home 3 Bedroom With Patio And A Game Room - Chesapeake, VA
9.5 180 reviews

5 Minutes To The Casino!family Sized Home 3 Bedroom With Patio And A Game Room

apartment, Portsmouth
This Portsmouth apartment is conveniently located just four minutes from Rivers Casino and fifteen minutes from the Waterside District, offering easy access to a range of attractions. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
The three-bedroom flat, spanning 130 square metres, comfortably sleeps up to eight guests. It boasts a fully equipped kitchen, a garden, a spa, a tennis court, and a range of entertainment options, including a pool table, darts, and a fire pit.

Best Chesapeake, VA holiday apartments with a balcony

Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews

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.
Charming 1-bedroom 1-bath Unit With Beautiful Riverfront Sunsets In Portsmouth - Chesapeake, VA
9.8 9 reviews

Charming 1-bedroom 1-bath Unit With Beautiful Riverfront Sunsets In Portsmouth

apartment, Portsmouth
This Portsmouth waterfront apartment, situated near Bon Secours Maryview Hospital (within 8km), offers easy access to the city's naval bases and the Waterside District.
The one-bedroom flat sleeps two, includes a full kitchen with dishwasher, in-unit laundry, smart TVs, a terrace, and free off-street parking, plus nearby access to a tree swing and shared porch.
Boutique Private 2nd Floor 2br Apartment  W/d  Near Casino & Downtown - Chesapeake, VA
No reviews

Boutique Private 2nd Floor 2br Apartment W/d Near Casino & Downtown

apartment, Portsmouth
This private upstairs flat in historic Westhaven, Portsmouth, is conveniently located 4 kilometres from Rivers Casino, 2 kilometres from Portsmouth City Park, and offers proximity to the Commodore Theatre and Portsmouth Naval Shipyard Museum.
This two-bedroom apartment accommodates up to four guests, featuring a kitchenette, a full-size washer and dryer, air conditioning, internet, and private off-street parking for one vehicle.
Historic Old Towne Southern Charm - Chesapeake, VA
9.4 41 reviews

Historic Old Towne Southern Charm

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.

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 Great Bridge Battlefield and Memorial, a significant site from the American Revolution. The Chesapeake Arboretum is a great place to learn about the local flora and fauna, and the Chesapeake Bay Foundation's Brock Environmental Center has exhibits about the Chesapeake Bay's ecosystem. For a taste of local history, the Chesapeake Historical Society Museum offers a glimpse into the city's past.
  • What are the best apartments in Chesapeake, VA?

  • What makes Chesapeake, VA unique or famous?

    Chesapeake is known for its beautiful waterfront, with the Chesapeake Bay providing stunning views and opportunities for water activities. It is also a city with a rich history, with sites like the Great Bridge Battlefield and Memorial, a significant battleground from the American Revolution. Chesapeake is also known for its diverse population, with a mix of urban and suburban areas, offering a variety of lifestyles.
  • 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?

    Chesapeake has a few farmers' markets, like the Chesapeake Farmers Market, where you can find local produce and crafts. For street food, you can try the food stalls at the Chesapeake City Park, especially during events. The Greenbrier area also has a few food trucks that pop up in different locations.
  • 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's public transportation system is primarily provided by Hampton Roads Transit (HRT). They offer buses that connect different parts of the city and nearby areas. However, it's worth noting that the system is not as extensive as in larger cities, so having a car is generally recommended for getting around Chesapeake.
  • 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 in the spring, offering tastings from local wineries. In the summer, the Chesapeake Bay Seafood Festival is a big draw, with fresh seafood and live music. The Chesapeake Fall Festival, held in October, is a great way to experience autumn with craft vendors and live entertainment.
  • What are the best pet friendly apartments in Chesapeake, VA?

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

    Apartments in Chesapeake usually include basic amenities like central air conditioning, a refrigerator, and a stove. Some apartments may also offer amenities like in-unit laundry, a dishwasher, or a balcony. It's best to check the specific listing for details.
  • What are the best apartments with parking in Chesapeake, VA?

Popular destinations

Best Chesapeake, VA holiday apartments with parking

Longer Stays Welcome! King Bed, Queen Bed, W/d - Chesapeake, VA
9.9 51 reviews

Longer Stays Welcome! King Bed, Queen Bed, W/d

apartment, Portsmouth
This Portsmouth apartment, near numerous shops including Kroger, TJ Maxx, and Walmart, and less than 1.6km from the Rivers Casino, offers convenient access to amenities.
The recently renovated two-bedroom, one-bathroom property sleeps four guests and boasts a private patio, modern amenities such as a dishwasher and air conditioning, and a washer/dryer.
Charming Efficiency! - Chesapeake, VA
9.8 55 reviews

Charming Efficiency!

apartment, Chesapeake
This Chesapeake flat boasts a central location offering easy access to major attractions such as Virginia Beach, Colonial Williamsburg, and Busch Gardens, with convenient interstate connections.
The self-catering studio apartment sleeps two, features a queen-size DreamCloud Premier mattress, 50" smart TV, full bathroom, and stainless steel appliances, and is close to various seafood restaurants and historical sites including the Battleship Wisconsin and the Hampton Roads Naval Museum.
Nyakio Suite - Chesapeake - Chesapeake, VA
No reviews

Nyakio Suite - Chesapeake

apartment, Chesapeake
This two-bedroom flat is located in Chesapeake's Greenbrier district, a 7-minute walk from Rivercrest Play Area and a 10-minute walk from Dominion Marketplace.
This 101 square metre residence accommodates up to four guests, featuring a fully equipped kitchen, air conditioning, Wi-Fi, a balcony, and access to an on-site swimming pool and parking.
The Magnolia Jem With A Private Entrance - Chesapeake, VA
No reviews

The Magnolia Jem With A Private Entrance

apartment, Suffolk
This Suffolk flat offers a central location, ideal for exploring nature and outdoor pursuits, with Town Point Park and Huntington Park a 27-kilometre drive away, and Riverfront Golf Club and Regal Harbour View Grande within a 6.5 to 8 kilometre radius.
This apartment accommodates two guests and provides essential amenities including Wi-Fi, air conditioning, towels, and a bidet, with nearby attractions such as Chesapeake Square Mall and Hampton Coliseum.

Best Chesapeake, VA holiday apartments with air conditioning

The Mayfield - Chesapeake, VA
9.6 22 reviews

The Mayfield

apartment, Portsmouth
This Portsmouth apartment, perfect for families or solo travellers, offers two bedrooms, one bathroom, and sleeps five, boasting excellent user, location and cleanliness ratings.
The self-catering flat includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and internet access.
Free Breakfast. Indoor Pool & Hot Tub. Near The Virginia Beach Business District! - Chesapeake, VA
No reviews

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.
Cozy Getaway Downtown Norfolk! - Chesapeake, VA
No reviews

Cozy Getaway Downtown Norfolk!

apartment, Norfolk
This one-bedroom flat is situated on Granby Street in Downtown Norfolk, a mere 500 meters from the Waterside waterfront and within easy reach of numerous dining, entertainment, and nightlife options.
This centrally located apartment offers accommodation for up to three guests, featuring a fully equipped kitchen with a microwave and dishwasher, air conditioning, and an in-unit washer and dryer, alongside a 50-inch television for your entertainment.
Olde Towne 4 Bedroom -2200 Sq Ft - Chesapeake, VA
9.4 334 reviews

Olde Towne 4 Bedroom -2200 Sq Ft

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.
©2026 cozycozy.com