Best apartment offers in Chesapeake, VA

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Chesapeake, VA apartments
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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

Trycam’s Humble Abode - Chesapeake, VA
9.2 44 reviews
Chesapeake, VA
09/07 – 14/07
A$372/nighttotal: A$1860 (5 )

Trycam’s Humble Abode

1 5
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.
Walk To The Casino! Sleeps 8, Close To Everything - Chesapeake, VA
9.6 110 reviews
Chesapeake, VA
29/06 – 03/08
A$303/nighttotal: A$10605 (35 )

Walk To The Casino! Sleeps 8, Close To Everything

1 2
apartment , Portsmouth
This Portsmouth apartment is conveniently located within walking distance of the casino and a short drive (under 10km) to Norfolk, Virginia Beach, and Chesapeake. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes with a fully equipped kitchen, laundry facilities, a private backyard, and smart home features, ensuring a comfortable and enjoyable stay.
Comfortable Retreat W/ Backyard & Parking - Chesapeake, VA
10 1 review
Chesapeake, VA
25/09 – 30/09
A$405/nighttotal: A$2025 (5 )

Comfortable Retreat W/ Backyard & Parking

2 4
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.
Family And Pet Friendly! - Chesapeake, VA
9.3 11 reviews
Chesapeake, VA
31/07 – 31/08
A$173/nighttotal: A$5363 (31 )

Family And Pet Friendly!

1 2
apartment , Portsmouth
This Portsmouth home, ideally located in Hampton Roads, offers easy access to Norfolk International Airport (approx. 3.5km) and attractions including the Norfolk Naval Shipyard (3.5km) and Rivers Casino (4.3km).
The two-bedroom, one-bathroom property sleeps four, features a well-equipped kitchen with modern appliances, a garden, parking, and air conditioning, plus allows dogs under 30lbs (upon approval).

Best Chesapeake, VA holiday apartments with a balcony

Beach Family Time Enjoy The Backyard Pool And Sunroom - Chesapeake, VA
8.6 36 reviews
Chesapeake, VA
25/09 – 30/09
A$1003/nighttotal: A$5015 (5 )

Beach Family Time Enjoy The Backyard Pool And Sunroom

3 4
apartment , Virginia Beach
This three-bedroom apartment in Virginia Beach is conveniently located just minutes from the beach and waterways, with easy access to Interstate 64. It has received very good ratings from previous guests and is ideal for families and groups.
The 260 square metre apartment comfortably sleeps up to 10 guests and comes with a range of amenities including a private pool, sunroom, top-deck bath, and a garden. Guests can enjoy activities such as jet skiing, kayaking, cave exploring, and mountain biking, as well as exploring the nearby cultural attractions and family-friendly activities.
Monthly, Dog-friendly Home At Orange Blossom - Chesapeake, VA
Chesapeake, VA
31/07 – 31/08
A$342/nighttotal: A$10602 (31 )

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.
Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood. - Chesapeake, VA
Chesapeake, VA
29/06 – 03/08
A$404/nighttotal: A$14140 (35 )

Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood.

1 2
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.
Beautiful Queen Luxury Suite Near Downtown Norfolk - Chesapeake, VA
8.3 33 reviews
Chesapeake, VA
25/09 – 30/09
A$223/nighttotal: A$1115 (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.

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

Free Breakfast. Indoor Pool & Hot Tub. Close To The Virginia Beach Business District! - Chesapeake, VA
8.0 4 reviews
Chesapeake, VA
08/07 – 13/07
A$584/nighttotal: A$2920 (5 )

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

1 5
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.
Escape To The Water! - Chesapeake, VA
10 22 reviews
Chesapeake, VA
09/07 – 14/07
A$427/nighttotal: A$2135 (5 )

Escape To The Water!

1 5
apartment , Portsmouth
This Portsmouth holiday home, located near the waterfront, offers easy access to attractions such as Prescott Park and Strawbery Banke Museum, though the precise distance is unspecified.
The two-bedroom, two-bathroom property sleeps six, features a fully equipped kitchen, air conditioning, parking, and internet access; guests can also enjoy lake access and two porches.
Country House Is Perfect For Remote Work Location - Chesapeake, VA
10 4 reviews
Chesapeake, VA
31/07 – 31/08
A$193/nighttotal: A$5983 (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.
Newly Renovated Vb Retreat | Comfort & Space Home - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
A$232/nighttotal: A$29928 (129 )

Newly Renovated Vb Retreat | Comfort & Space Home

3 2
apartment , Virginia Beach
This Virginia Beach rental property is located in a tranquil neighbourhood, offering convenient access to the oceanfront, Sandbridge Beach, Chesapeake Bay, Greenbrier Mall, and Pacific Avenue.
This 100 square metre flat offers three bedrooms, two bathrooms, and accommodates up to nine guests, featuring a spacious open-concept layout with vaulted ceilings, a well-equipped kitchen, and a comfortable living room with a fireplace and large television.

Best Chesapeake, VA holiday apartments with air conditioning

The Liberty Flat - Chesapeake, VA
10 21 reviews
Chesapeake, VA
25/09 – 30/09
A$210/nighttotal: A$1050 (5 )

The Liberty Flat

1 4
apartment , Portsmouth
This Olde Town Portsmouth flat, situated a short ferry journey from Norfolk and within walking distance of local restaurants, offers easy access to Virginia Beach, Norfolk, Williamsburg, and Yorktown.
The two-bedroom, one-bathroom apartment sleeps four, includes a kitchen with amenities for self-catering, and is anticipated to feature a washer/dryer; access is via stairs to the second floor.
The Rosalie Suite 1, Steps From Norfolks Hospitals - Chesapeake, VA
9.5 423 reviews
Chesapeake, VA
29/06 – 03/08
A$272/nighttotal: A$9520 (35 )

The Rosalie Suite 1, Steps From Norfolks Hospitals

1 2
apartment , Norfolk
This one-bedroom flat is located in downtown Norfolk, within easy walking distance of Sentara Norfolk General Hospital, Old Dominion University, Eastern Virginia Medical School, and the Chrysler Museum of Art. It has received excellent ratings for location, cleanliness, and user experience.
The 46 square metre flat comfortably sleeps two guests and is equipped with a fully fitted kitchen, a washing machine, a TV, and a coffee maker. It also benefits from a terrace, a garden, parking, and air conditioning, making it ideal for a relaxing stay in Norfolk.
Sojourn At Colley Manor Unit 2 - Chesapeake, VA
10 2 reviews
Chesapeake, VA
31/07 – 31/08
A$207/nighttotal: A$6417 (31 )

Sojourn At Colley Manor Unit 2

2 2
apartment , Norfolk
This Ghent flat in Norfolk is centrally located near Colley Avenue's restaurants and shops, within easy reach (by foot, bike, bus, or Tide light rail) of Norfolk city centre and major hospitals such as CHKD and Norfolk General Hospital, and a short drive (approximately 20-30 km) from Virginia Beach and Ocean View Beach.
This 93-square-metre (1000 sq ft) two-bedroom, one-bathroom apartment sleeps four, offering self-check-in, a fully equipped kitchen (including fridge, microwave, and dishwasher), air conditioning, parking, and internet access; pack 'n' play and high chair rentals are available for families.
The Cozy Cottage Two Bedroom, King Bed House - Chesapeake, VA
9.9 131 reviews
Chesapeake, VA
23/06 – 25/06
A$475/nighttotal: A$950 (2 )

The Cozy Cottage Two Bedroom, King Bed House

1 3
apartment , Chesapeake
This charming Cape Cod style house is located in a central area of Chesapeake, within easy reach of local attractions and landmarks. The property has received excellent ratings for cleanliness, location and user experience.
The house has two bedrooms, one bathroom and can accommodate up to four guests. It is equipped with modern amenities including air conditioning, a fully equipped kitchen and smart TVs in every room.
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