Holiday 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

2br Self Check-in, Fast Wi-fi - Chesapeake, VA
9.9 59 reviews
Chesapeake, VA
17/07 – 20/07
247 €/nighttotal: 741 € (3 )

2br Self Check-in, Fast Wi-fi

1 2
apartment , Chesapeake
This apartment is conveniently located just a short drive from Virginia Beach, offering easy access to the beach, boardwalk, and various attractions. It has excellent user, location, and cleanliness ratings, making it a great choice for travellers.
The apartment comfortably sleeps four guests and features a spacious living area, two bedrooms, and a modern bathroom. It has a well-equipped kitchen with a fridge, freezer, microwave, dishwasher, and a washing machine and dryer, making it perfect for self-catering.
11 Mi To Virginia Beach Boardwalk: Studio Retreat! - Chesapeake, VA
8.0 3 reviews
Chesapeake, VA
25/09 – 30/09
127 €/nighttotal: 635 € (5 )

11 Mi To Virginia Beach Boardwalk: Studio Retreat!

1 2
studio , Virginia Beach
This Northwest Virginia Beach apartment is ideally situated 1.6km from the Virginia Beach Town Centre, offering easy access to shopping, dining, and the beach.
The 33-square-metre self-catering studio sleeps two, features a kitchenette with microwave, mini-fridge and Keurig coffee maker, a shared backyard, and complimentary toiletries, plus driveway parking and a smart TV; nearby attractions include the Virginia Aquarium & Marine Science Center, First Landing State Park, and the Military Aviation Museum.
King Guest Suite - A Togar Vacation Rental - Chesapeake, VA
9.8 355 reviews
Chesapeake, VA
17/07 – 20/07
151 €/nighttotal: 453 € (3 )

King Guest Suite - A Togar Vacation Rental

1 2
apartment , Chesapeake
This one-bedroom flat is located in Deep Creek South, Chesapeake, just a short drive from the Cahoon Plantation Golf Course and the Great Dismal Swamp National Wildlife Refuge. It has received excellent ratings for location, cleanliness and overall experience.
The apartment has a bathroom and can accommodate up to three guests. It offers a range of amenities, including a fully equipped kitchen, a private patio, a washing machine, and a garden, making it ideal for a relaxing stay.
Sojourn | Virginia Beach | 2 Bedroom Townhouse - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
217 €/nighttotal: 27993 € (129 )

Sojourn | Virginia Beach | 2 Bedroom Townhouse

2 2
apartment , Virginia Beach
This two-bedroom flat in Northwest Virginia Beach is situated opposite Virginia Wesleyan College, providing easy access to military bases such as Joint Base Little Creek (8 kilometres away), Norfolk Naval Station (16 kilometres away), and Master Jet Base Oceana (17.7 kilometres away), as well as Sentara Leigh Hospital (3.2 kilometres away).
This family-friendly residence accommodates up to five guests with a fully equipped kitchen, including a fridge, microwave, and dishwasher, air conditioning, Wi-Fi, smart TVs with Hulu Live and Netflix, and a garden, with parking available and a check-out time of 11:00 AM.

Best Chesapeake, VA holiday rentals with parking

Downtown Norfolk Loft - Chesapeake, VA
9.7 104 reviews
Chesapeake, VA
01/12 – 29/12
179 €/nighttotal: 5012 € (28 )

Downtown Norfolk Loft

1 2
apartment , Norfolk
The Downtown Norfolk Loft apartment is located in the city centre, just 11.6 kilometres from Topgolf Virginia Beach, 17.7 kilometres from Mount Trashmore Park and 25.7 kilometres from Virginia Beach National Golf Club. This one-bedroom apartment has received excellent ratings for its location, cleanliness and overall experience.
This comfortable flat is 98 square metres and can accommodate up to two guests. It comes with a fully equipped kitchen, air conditioning, free Wi-Fi and parking, making it ideal for a relaxing stay in Norfolk.
Free Breakfast. Indoor Pool & Hot Tub. Near The Virginia Beach Business District! - Chesapeake, VA
Chesapeake, VA
25/09 – 30/09
278 €/nighttotal: 1390 € (5 )

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

1 4
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.
Modern Apartment Stay With Fast Wi-fi And Workspace - Chesapeake, VA
Chesapeake, VA
01/12 – 29/12
58 €/nighttotal: 1624 € (28 )

Modern Apartment Stay With Fast Wi-fi And Workspace

1 2
apartment , Portsmouth
This modernly furnished flat is located in Portsmouth, providing convenient access to Portsmouth Naval Shipyard, Portsmouth Regional Hospital, and various major employers, with the Veterans United Home Loans Amphitheater at Virginia Beach situated approximately 10 kilometers away.
This one-bedroom, one-bathroom apartment accommodates two guests and features high-speed Wi-Fi, a dedicated workspace, a fully equipped kitchen with a fridge and microwave, air conditioning, and on-site parking.
Newly Remodeled 2 Bedroom Duplex - Chesapeake, VA
10 2 reviews
Chesapeake, VA
31/07 – 31/08
123 €/nighttotal: 3813 € (31 )

Newly Remodeled 2 Bedroom Duplex

2 2
apartment , Chesapeake
This newly renovated flat is located in the Great Bridge neighbourhood of Chesapeake, a quiet area just a short drive from Jillian's Billiards and the Currituck County Welcome Center. The apartment is ideal for families or groups of up to 3 people, offering 2 bedrooms and 1 bathroom.
The flat comes equipped with a modern kitchen, including a fridge, microwave, and dishwasher, as well as a jacuzzi, parking, and free Wi-Fi. Enjoy the convenience of a washer and dryer, and relax on the comfortable sofas in front of the 65-inch Smart TV.

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 or September to October, as the weather is still pleasant but the crowds are smaller. You'll find better deals on rentals during these months.
  • What are the best Airbnb and holiday rentals in Chesapeake, VA?

  • What events or festivals should visitors check out in and around Chesapeake, VA?

    Chesapeake has a few great events, like the Chesapeake Bay Wine Festival in the spring, and the Chesapeake Bay Seafood Festival in the fall. It's a great way to experience local culture and sample some delicious food and drink.
  • What are the most popular Airbnbs in Chesapeake, VA?

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

    Chesapeake has a lot to offer without breaking the bank. You can enjoy a free walk along the Chesapeake Bay Trail, or take a picnic to the Chesapeake Arboretum. There are also plenty of free concerts and events held throughout the year.
  • 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 best restaurants with local dishes in Chesapeake, VA?

    If you're looking for a taste of Chesapeake, you should try the Chesapeake Bay Blue Crab at one of the local restaurants. The Crabby Shack and The Blue Crab are two popular options that serve up some delicious seafood.
  • 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 walking or cycling routes in Chesapeake, VA?

    The Chesapeake Bay Trail is a great option for walking or cycling, it stretches for over 160 km and offers stunning views of the Chesapeake Bay. The Great Bridge Trail is another popular choice, it's a shorter trail, but it's perfect for a leisurely bike ride.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesapeake, VA?

    The best vacation 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.

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

    Yes, there are a few pet-friendly attractions in Chesapeake. The Chesapeake Arboretum welcomes dogs on leash, and the Chesapeake Bay Trail is also dog-friendly. Many restaurants also have outdoor seating areas that are pet-friendly.
  • What are the benefits of choosing a vacation rental in Chesapeake, VA?

    Vacation rentals offer more space and privacy than a hotel room, and they are often more affordable, especially for families or groups. You'll also have access to a kitchen, which allows you to save money by preparing some of your own meals.
  • What are the top sports attractions and facilities in Chesapeake, VA?

    The Chesapeake Sports Complex is a popular destination for sports fans, it has several fields for baseball, softball, and soccer, as well as a track and field facility. The Chesapeake YMCA also offers a range of sports programs and facilities, including a swimming pool and fitness centre.

Destinations nearby

Best Chesapeake, VA holiday rentals with a balcony

Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
10 1 review
Chesapeake, VA
12/10 – 18/02
156 €/nighttotal: 20124 € (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.
Luxe Lakefront Portsmouth Home Fish, Swim And Play! - Chesapeake, VA
10 2 reviews
Chesapeake, VA
01/12 – 29/12
418 €/nighttotal: 11704 € (28 )

Luxe Lakefront Portsmouth Home Fish, Swim And Play!

3 2
house , Portsmouth
This lakefront holiday home is located in Portsmouth, just 24km from the Norfolk Botanical Garden and 40km from the King Neptune Statue on the Boardwalk, offering a peaceful retreat close to attractions.
This spacious property has 3 bedrooms, 3 bathrooms, and can comfortably accommodate up to 15 guests. The home is equipped with a range of amenities, including a fully equipped kitchen, air conditioning, a swimming pool, a spa, a garden, parking, and free Wi-Fi, ensuring a comfortable and enjoyable stay for all.
Historic Old Towne Southern Charm - Chesapeake, VA
9.6 37 reviews
Chesapeake, VA
25/09 – 30/09
160 €/nighttotal: 800 € (5 )

Historic Old Towne Southern Charm

2 2
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.
Norfolk 3br Cozy Stay. Central To All & Comfort. Families & Contractors! - Chesapeake, VA
10 7 reviews
Chesapeake, VA
27/06 – 04/07
413 €/nighttotal: 2891 € (7 )

Norfolk 3br Cozy Stay. Central To All & Comfort. Families & Contractors!

3 3
apartment , Norfolk
This charming apartment is located in Norfolk, just 2 kilometres from the Virginia Zoo and 5 kilometres from the Norfolk Scope. It has been rated excellent by previous guests.
The apartment has 3 bedrooms and 2 bathrooms, providing comfortable accommodation for up to 6 guests. It comes equipped with a kitchen, air conditioning, a Jacuzzi, a terrace, parking, and Wi-Fi, allowing you to relax and enjoy your stay.

Best Chesapeake, VA holiday rentals with air conditioning

An Entire House In Va Beach...just For Two! - Chesapeake, VA
9.7 72 reviews
Chesapeake, VA
27/06 – 04/07
187 €/nighttotal: 1309 € (7 )

An Entire House In Va Beach...just For Two!

1 2
apartment , Virginia Beach
This Virginia Beach ranch-style house, offering complete privacy, is conveniently located in an unspecified area of the city; precise proximity to landmarks requires further clarification.
The single-bedroom property boasts two bathrooms, a full kitchen with fridge, microwave, and dishwasher, and accommodates up to two guests, with a ground-level deck and off-street parking.
Waterfront Oasis: Fishing Pier, Pool, Beach Access - Chesapeake, VA
10 4 reviews
Chesapeake, VA
25/09 – 30/09
361 €/nighttotal: 1805 € (5 )

Waterfront Oasis: Fishing Pier, Pool, Beach Access

3 4
house , Chesapeake
This Chesapeake flat is located in the Deep Creek district, directly on the Elizabeth River, offering waterfront living with private marina club access, a fishing pier, docks, and beach access.
This 3-bedroom, 2-bathroom residence accommodates up to 8 guests and features air conditioning, internet, a kitchen, swimming pool, fitness centre, parking, and a dedicated dog park.
"The Ponderosa B" - Close To The Casino & Concerts - Chesapeake, VA
9.9 152 reviews
Chesapeake, VA
14/08 – 16/08
119 €/nighttotal: 238 € (2 )

"The Ponderosa B" - Close To The Casino & Concerts

1 2
apartment , Portsmouth
This one-bedroom flat is conveniently located just 800 metres from Rivers Casino, offering easy access to Portsmouth and Norfolk city centres. The property has received excellent ratings for location, cleanliness, and overall experience.
The apartment is ideal for couples, with a private entrance and parking. Guests can enjoy comfortable amenities like a fully equipped kitchen, air conditioning, and laundry services available for longer stays.
The Rosalie Suite 1, Steps From Norfolks Hospitals - Chesapeake, VA
9.5 423 reviews
Chesapeake, VA
29/06 – 03/08
166 €/nighttotal: 5810 € (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.
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