Vacation Rentals in Chesapeake, VA

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Chesapeake, VA holiday rentals
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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

Lighthouse Launch - Spacious 4 Br/2ba Retreat - Chesapeake, VA
9.5 41 reviews
Chesapeake, VA
16/08 – 27/08
A$354/nighttotal: A$3894 (11 )

Lighthouse Launch - Spacious 4 Br/2ba Retreat

1 4
apartment , Portsmouth
This four-bedroom, two-bathroom house in a quiet Portsmouth neighbourhood is a short drive (approx. 5km) from Portsmouth's waterfront and around 48km from Virginia Beach.
This self-catering property sleeps eight, boasting a fully equipped kitchen, high-speed Wi-Fi, a Smart TV, and a washer/dryer, alongside exterior security cameras and a decibel monitor for a peaceful stay.
Modern Luxury Peace & Quiet. - Chesapeake, VA
10 181 reviews
Chesapeake, VA
31/07 – 31/08
A$347/nighttotal: A$10757 (31 )

Modern Luxury Peace & Quiet.

1 2
apartment , Chesapeake
This modern guest house apartment is located in a peaceful residential area in Chesapeake, just 10km from restaurants and shops, 39km from the Chesapeake Amphitheater, and 52km from the beach. The property has received excellent ratings for its cleanliness, location, and overall guest experience.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, a private garden, a fitness centre, and a range of amenities for a comfortable and enjoyable stay, including free parking, high-speed Wi-Fi, and access to bicycles for exploring the local area.
Waterfront Oasis With Fenced Yard - Chesapeake, VA
9.7 295 reviews
Chesapeake, VA
25/09 – 30/09
A$434/nighttotal: A$2170 (5 )

Waterfront Oasis With Fenced Yard

1 4
house , Chesapeake
This charming townhouse is situated in Chesapeake, within easy reach of various landmarks, offering a peaceful lakefront setting with a tranquil atmosphere. It boasts excellent ratings for user experience, location, and cleanliness.
The property features an open-plan layout, perfect for families or groups of up to 8 guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and a laundry room on the second floor, ensuring a comfortable and convenient stay.
Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
10 1 review
Chesapeake, VA
12/10 – 18/02
A$256/nighttotal: A$33024 (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 rentals with parking

Spacious Chesapeake Home With Pool Table! - Chesapeake, VA
9.3 3 reviews
Chesapeake, VA
09/07 – 14/07
A$584/nighttotal: A$2920 (5 )

Spacious Chesapeake Home With Pool Table!

4 5
house , Chesapeake
This spacious holiday home is located in Chesapeake, just 23 kilometres from Topgolf Virginia Beach and 29 kilometres from Mount Trashmore Park. The property has received excellent ratings for user experience, location, and cleanliness.
The four-bedroom house is 223 square metres in size and can accommodate up to eight guests. This property offers a range of amenities including a fully equipped kitchen, a pool table, free Wi-Fi, cable TV, a washing machine and towels and bed linen are provided.
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.
Walk To River And Downtown Portsmouth Apartment! - Chesapeake, VA
Chesapeake, VA
16/08 – 27/08
A$316/nighttotal: A$3476 (11 )

Walk To River And Downtown Portsmouth Apartment!

2 4
house , Portsmouth
This Portsmouth apartment, located a short walk from the Riverfront and Portsmouth city centre, is approximately 14.5 kilometres from Norfolk Botanical Garden and 14 kilometres from Norfolk International Airport.
This two-bedroom holiday home offers 111 square metres of space, sleeping up to seven guests and boasting free Wi-Fi, a fully equipped kitchen, and private parking.
Free Breakfast. Indoor Pool & Hot Tub. Close To The Virginia Beach Business District! - Chesapeake, VA
8.0 4 reviews
Chesapeake, VA
25/09 – 30/09
A$496/nighttotal: A$2480 (5 )

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

1 4
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.

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. The weather is still pleasant, but the crowds are smaller and prices are often lower. The summer months, June to August, are popular with tourists, so expect higher prices and larger crowds.
  • What are the best Airbnb and holiday rentals in Chesapeake, VA?

  • What are the best budget-friendly activities in Chesapeake, VA?

    Chesapeake offers many budget-friendly activities, including a visit to the Chesapeake Arboretum, exploring the Chesapeake Bay waterfront, or taking a walk or bike ride on the Chesapeake Bay Trail. You can also enjoy a picnic lunch at the Chesapeake City Park or spend an afternoon browsing the shops and restaurants in the Greenbrier area.
  • What are the most popular Airbnbs in Chesapeake, VA?

  • What are the best restaurants with local dishes in Chesapeake, VA?

    For a taste of local seafood, try the Chesapeake Bay Bridge-Tunnel Seafood Restaurant. If you prefer something a bit more casual, try the Chesapeake Bay Brewing Company, which offers a range of craft beers and pub grub. For a more upscale dining experience, try the Chesapeake Inn, which offers a fine-dining menu with a focus on fresh, local ingredients.
  • What are the best holiday rentals with a pool in Chesapeake, VA?

    Modern Condo In Western Branch, The Peaceful Oasis and Cheshire Retreat are the best holiday rentals with a pool in Chesapeake, VA.

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

    The Chesapeake Bay Trail is a popular choice for walking and cycling, offering scenic views of the Chesapeake Bay. The trail is over 160km long and runs through various parts of the city, including the Chesapeake Arboretum and the Chesapeake City Park. For a shorter walk, you can explore the trails at the Chesapeake Arboretum or the Chesapeake Botanical Gardens.
  • 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.

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

    Yes, Chesapeake is a pet-friendly city. The Chesapeake Arboretum welcomes dogs on leash, and the Chesapeake City Park has a dedicated dog park. Many restaurants also have outdoor seating where you can bring your furry friend.
  • 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.

  • What are the benefits of choosing a vacation rental in Chesapeake, VA?

    Vacation rentals offer a more spacious and comfortable alternative to hotels. They are often located in residential areas, which can provide a more authentic experience of the city. They also offer more privacy and flexibility than traditional accommodations, allowing you to prepare your own meals and set your own schedule.
  • What are the top sports attractions and facilities in Chesapeake, VA?

    Chesapeake is home to the Chesapeake Regional Healthcare YMCA, which offers a range of fitness and sports facilities, including a swimming pool, a gymnasium, and a fitness centre. For outdoor activities, the Chesapeake City Park offers a variety of sports facilities, including baseball fields, tennis courts, and a skate park.

Destinations nearby

Best Chesapeake, VA holiday rentals with a balcony

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.
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
A$531/nighttotal: A$1062 (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.
Charming 2 Br Vintage Duplex Upstairs Apartment In Historic Portsmouth Ac & Wifi - Chesapeake, VA
9.0 7 reviews
Chesapeake, VA
24/07 – 26/07
A$408/nighttotal: A$816 (2 )

Charming 2 Br Vintage Duplex Upstairs Apartment In Historic Portsmouth Ac & Wifi

2 4
apartment , Portsmouth
This Portsmouth apartment is conveniently located near the Children's Museum of Virginia and the Portsmouth Naval Shipyard Museum, approximately 1.8 km away.
The two-bedroom, one-bathroom flat sleeps four guests and features a terrace, garden, fully equipped kitchen including oven, microwave and coffee maker, plus in-unit laundry facilities and free Wi-Fi.
Fenced Yard And Patio! 2,400-sq-ft Chesapeake Home - Chesapeake, VA
10 1 review
Chesapeake, VA
16/08 – 27/08
A$839/nighttotal: A$9229 (11 )

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

Entire Apartment In Chesapeake, Virginia - Chesapeake, VA
10 1 review
Chesapeake, VA
25/09 – 30/09
A$300/nighttotal: A$1500 (5 )

Entire Apartment In Chesapeake, Virginia

2 4
apartment , Chesapeake
This centrally located flat in Chesapeake offers excellent access to Hampton Roads attractions, being just a 2-minute drive from the I64 motorway, placing it minutes from the Oceanfront and Downtown Norfolk.
This spacious, pet-friendly apartment with high ceilings accommodates up to four guests, featuring two bathrooms, a fully equipped kitchen with a Keurig and rice cooker, a Smart TV with Netflix, a private balcony, and optional weekly cleaning for longer stays.
Tasha's Townhouse *King, Queen, Twin* - Chesapeake, VA
9.7 234 reviews
Chesapeake, VA
25/09 – 30/09
A$270/nighttotal: A$1350 (5 )

Tasha's Townhouse *King, Queen, Twin*

3 4
house , Chesapeake
This house is located in the Greenbrier area of Chesapeake, within easy walking distance of a park, lake, restaurants, and shops. It has received excellent ratings for location, cleanliness, and user experience.
The house has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes with a fully equipped kitchen, air conditioning, a garden, parking, and a Ring Doorbell camera for added security.
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.
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.
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