Holiday Rentals in Chesapeake, VA

677 available vacation rental offers

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

677 Holiday Rentals and Airbnb in Chesapeake, VA

Best family friendly Chesapeake, VA holiday rentals

Among the 677 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals

Portsmouth 3br Near Casino, Comfy, Spacious Yard Stay, Sleeps 6! - Chesapeake, VA
9.0 15 reviews
Chesapeake, VA
31/07 – 31/08
NZ$486/nighttotal: NZ$15066 (31 )

Portsmouth 3br Near Casino, Comfy, Spacious Yard Stay, Sleeps 6!

3 2
apartment , Portsmouth
This Portsmouth holiday home is situated within 3km of the Commodore Theatre, Virginia Sports Hall of Fame and Museum, and Children's Museum of Virginia, and within 5km of the Portsmouth Naval Shipyard Museum.
The 130 square metre property boasts three bedrooms sleeping six, two bathrooms, a fully equipped kitchen, a jacuzzi, a terrace, a garden, parking, and free Wi-Fi; nearby attractions include the Tidewater Yacht Marina.
Spaccomf-4bd2ba-sleeps8-parking-i164-hosp-3daysmin - Chesapeake, VA
9.8 38 reviews
Chesapeake, VA
08/07 – 13/07
NZ$962/nighttotal: NZ$4810 (5 )

Spaccomf-4bd2ba-sleeps8-parking-i164-hosp-3daysmin

1 5
apartment , Portsmouth
This spacious home is located in a peaceful neighbourhood in Portsmouth, Virginia, just 15 kilometres from the Norfolk Naval Shipyard and Portsmouth Naval Hospital. The property has consistently received excellent ratings for its cleanliness, location, and overall user experience.
The house has four bedrooms and two bathrooms, comfortably accommodating up to 12 guests. Amenities include a fully equipped kitchen, a garden, parking for seven vehicles, air conditioning, and a range of games and toys for families.
Olde Towne 4 Bedroom -2200 Sq Ft - Chesapeake, VA
9.4 313 reviews
Chesapeake, VA
25/09 – 30/09
NZ$259/nighttotal: NZ$1295 (5 )

Olde Towne 4 Bedroom -2200 Sq Ft

1 4
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.
Cozy Cute Apartment - Chesapeake, VA
10 23 reviews
Chesapeake, VA
14/08 – 16/08
NZ$175/nighttotal: NZ$350 (2 )

Cozy Cute Apartment

1 2
apartment , Portsmouth
This one-bedroom flat in Portsmouth is centrally located, offering immediate access to Old Town Portsmouth's dining and entertainment, and is just 600 meters from City Park.
This pet-friendly apartment accommodates two guests, features air conditioning and parking, and is conveniently situated for day trips to Norfolk beaches (32 kilometres away) and attractions like Oceanfront and Busch Gardens (64 kilometres away).

Best Chesapeake, VA holiday rentals with parking

Sojourn At Colley Manor Unit 5 Sleeps 4 - Chesapeake, VA
Chesapeake, VA
01/07 – 31/07
NZ$284/nighttotal: NZ$8520 (30 )

Sojourn At Colley Manor Unit 5 Sleeps 4

2 2
apartment , Norfolk
Colley Manor Unit 5, a two-bedroom apartment in Norfolk, is situated 10km from Norfolk International Airport and 10.6km from the Norfolk Botanical Garden, offering convenient access to key attractions.
This 84 square metre self-catering flat sleeps six guests and includes a fully equipped kitchen with dishwasher, in-unit laundry facilities, free Wi-Fi, and air conditioning.
Lakefront | Sunset Views | Great Central Location! - Chesapeake, VA
10 1 review
Chesapeake, VA
19/07 – 18/10
NZ$186/nighttotal: NZ$16926 (91 )

Lakefront | Sunset Views | Great Central Location!

2 1
house , Chesapeake
This Chesapeake lakeside townhouse, situated near the Virginia Beach border, offers easy access to both cities and their attractions.
The two-bedroom, two-bathroom property sleeps four guests and includes a fully equipped kitchen, smart TVs, private deck with sunset views, and amenities such as a washer/dryer and parking for two vehicles.
Cozy Portsmouth Retreat 2br/1ba - Chesapeake, VA
10 1 review
Chesapeake, VA
25/09 – 30/09
NZ$377/nighttotal: NZ$1885 (5 )

Cozy Portsmouth Retreat 2br/1ba

2 4
apartment , Portsmouth
This Portsmouth apartment, ideally located for exploring the city, is a short 6.4km drive from the Children's Museum of Virginia and 8km from the Portsmouth Naval Shipyard Museum.
The 102 square metre property sleeps six guests and boasts two bedrooms, one bathroom, a fully equipped kitchen, in-unit laundry, air conditioning, parking, and Wi-Fi; nearby attractions include the Waterside District and Virginia Beach Town Centre.
Virginia Beach, Getaway - Chesapeake, VA
9.8 51 reviews
Chesapeake, VA
23/06 – 25/06
NZ$293/nighttotal: NZ$586 (2 )

Virginia Beach, Getaway

1 3
apartment , Virginia Beach
This modern one-bedroom apartment in Virginia Beach is situated on a quiet cul-de-sac, minutes from Lynnhaven Inlet, local shops, restaurants, and beaches, as well as the Virginia Beach Convention Center and sports facilities.
The self-catering flat offers two queen-size beds sleeping up to four guests, a fully equipped kitchen, in-unit laundry, and a newly fitted bathroom; enjoy easy access to the area's attractions.

Frequently asked questions about holiday rentals in Chesapeake, VA

  • When is the best time to book a vacation rental in Chesapeake, VA?

    The best time to book a vacation rental in Chesapeake is during the shoulder seasons, from April to May and September to October. You'll find fewer crowds and more affordable rates during these months. The weather is still pleasant, and you can enjoy all the attractions without the summer rush.
  • What are the best Airbnb and holiday rentals in Chesapeake, VA?

  • What are the best walking or cycling routes in Chesapeake, VA?

    The Chesapeake Bay Trail is a popular walking and cycling route that stretches along the Chesapeake Bay waterfront. The Great Bridge Battlefield and Waterways History Trail is another good option, offering a scenic route through the historic Great Bridge area. For a shorter walk, try the Chesapeake Arboretum's nature trails.
  • What are the most popular Airbnbs in Chesapeake, VA?

  • Are there pet-friendly attractions in Chesapeake, VA?

    The Chesapeake Arboretum is pet-friendly, and you can bring your furry friend along for a walk on the trails. The Chesapeake Bay Maritime Museum also welcomes well-behaved dogs on a leash.
  • What are the best holiday rentals with a pool in Chesapeake, VA?

    Modern Condo In Western Branch, Comfortable Home | Long Stay Discount Available and The Peaceful Oasis are the best holiday rentals with a pool in Chesapeake, VA.

  • What are the top sports attractions and facilities in Chesapeake, VA?

    The Chesapeake Regional Healthcare YMCA offers a variety of fitness classes, swimming pools, and sports courts. The Chesapeake City Park has tennis courts, baseball fields, and a playground. For golf enthusiasts, the Chesapeake Golf Club offers a challenging 18-hole course.
  • What are the best rentals for families and kids in Chesapeake, VA?

    The best rentals for families and kids in Chesapeake, VA are King Guest Suite - A Togar Vacation Rental, Townhome In Convient Location and Modern Luxury Peace & Quiet.

  • What are the best rentals or Airbnbs with a jacuzzi in Chesapeake, VA?

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

Destinations nearby

Best Chesapeake, VA holiday rentals with a balcony

Historic Old Towne Southern Charm - Chesapeake, VA
9.6 35 reviews
Chesapeake, VA
25/09 – 30/09
NZ$319/nighttotal: NZ$1595 (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
NZ$550/nighttotal: NZ$2750 (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.
Bright Chesapeake Home Near Shopping And Dining - Chesapeake, VA
10 9 reviews
Chesapeake, VA
23/06 – 25/06
NZ$787/nighttotal: NZ$1574 (2 )

Bright Chesapeake Home Near Shopping And Dining

2 3
house , Chesapeake
This two-bedroom house in Chesapeake, Virginia is conveniently located just 15 miles from Topgolf Virginia Beach and 19 miles from Mount Trashmore Park, offering easy access to both entertainment and nature. It has consistently received excellent ratings for user experience, location, and cleanliness, indicating a high standard of comfort and satisfaction for guests.
The 93 square metre property comfortably accommodates up to four guests and features a fully equipped kitchen, a private patio, and a spa. Guests can enjoy modern amenities such as free Wi-Fi, a cable flat-screen TV, and a washing machine, as well as a range of activities like golfing at the Virginia Beach National Golf Club and exploring the Virginia Living Museum.
Fenced Yard And Patio! 2,400-sq-ft Chesapeake Home - Chesapeake, VA
10 1 review
Chesapeake, VA
25/09 – 30/09
NZ$1104/nighttotal: NZ$5520 (5 )

Fenced Yard And Patio! 2,400-sq-ft Chesapeake Home

4 4
house , Chesapeake
This Chesapeake holiday home, situated 16km from Norfolk, offers easy access to attractions such as the Norfolk Botanical Garden (27km) and the King Neptune Statue (45km).
The 223 square metre property boasts four bedrooms, three bathrooms, sleeps fifteen guests, and includes a fully equipped kitchen, Wi-Fi, air conditioning, a garden, a spa, and on-site parking.

Best Chesapeake, VA holiday rentals with air conditioning

Private Boutique Apt •W/d• Near Casino & Downtown - Chesapeake, VA
9.8 13 reviews
Chesapeake, VA
25/09 – 30/09
NZ$228/nighttotal: NZ$1140 (5 )

Private Boutique Apt •W/d• Near Casino & Downtown

1 4
apartment , Portsmouth
This Westhaven flat is situated in Portsmouth, offering historic character and convenient access to Rivers Casino, NNSY, and Naval Station Norfolk, all within a few kilometres.
This two-bedroom residence accommodates up to four guests and includes a kitchenette, air conditioning, private parking, and an in-unit washer/dryer for a comfortable stay.
Portsmouth 2br/1ba Getaway - Chesapeake, VA
10 2 reviews
Chesapeake, VA
16/08 – 27/08
NZ$294/nighttotal: NZ$3234 (11 )

Portsmouth 2br/1ba Getaway

2 4
apartment , Portsmouth
This Portsmouth holiday home is situated within 4.8km of attractions including the Commodore Theatre, the Virginia Sports Hall of Fame and Museum, and the Children's Museum of Virginia.
The 102 square metre property sleeps six guests and boasts two bedrooms, one bathroom, a fully equipped kitchen, garden, parking, and a smoke-free environment.
Great, Classy Two-bedroom, Near Rivers Casino. - Chesapeake, VA
9.5 4 reviews
Chesapeake, VA
24/07 – 26/07
NZ$465/nighttotal: NZ$930 (2 )

Great, Classy Two-bedroom, Near Rivers Casino.

1 4
apartment , Portsmouth
This Portsmouth apartment is situated minutes from the Interstate, offering easy access to other parts of New Hampshire whilst enjoying a peaceful neighbourhood setting.
The self-catering property sleeps four guests in two bedrooms (one queen, one double bed) and includes a kitchen, bathroom, air conditioning, parking, and internet access.
Cozy Studio Getaway - Chesapeake, VA
Chesapeake, VA
29/06 – 03/08
NZ$217/nighttotal: NZ$7595 (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.
©2026 cozycozy.com