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

5 Minutes To The Casino!family Sized Home 3 Bedroom With Patio And A Game Room - Chesapeake, VA
9.6 169 reviews
Chesapeake, VA
25/09 – 30/09
194 €/nighttotal: 970 € (5 )

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

3 4
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.
Clean Spacious Home Near Sentara Hospital - Chesapeake, VA
9.5 62 reviews
Chesapeake, VA
29/06 – 03/08
250 €/nighttotal: 8750 € (35 )

Clean Spacious Home Near Sentara Hospital

4 2
apartment , Norfolk
This Norfolk house is located within 3km of Harbor Park, MacArthur Center, and the Douglas MacArthur Memorial, offering easy access to Norfolk's attractions and a central location. The property has received excellent ratings for user experience, location, and cleanliness.
This spacious house has 3 bedrooms and a sofa bed, making it suitable for families or groups. The house also features a fully equipped kitchen, free Wi-Fi, a relaxing garden, and parking, ensuring a comfortable stay.
Duplex W/fast Wi-fi & Stocked Kitchen - Chesapeake, VA
10 1 review
Chesapeake, VA
16/08 – 27/08
181 €/nighttotal: 1991 € (11 )

Duplex W/fast Wi-fi & Stocked Kitchen

2 4
apartment , Portsmouth
This 2-bedroom, 1-bathroom duplex in Portsmouth's Brighton district offers proximity to the Portsmouth Shipyard, just 500 meters away, and is a 10-minute drive from the city centre's amenities.
This family-friendly flat accommodates up to 7 guests, featuring a fully equipped kitchen with a fridge and microwave, air conditioning, free Wi-Fi, and on-site parking, making it ideal for shipyard workers or families visiting Portsmouth.
Park View Place - Apt 1 - Historic Olde Towne - Chesapeake, VA
8.6 37 reviews
Chesapeake, VA
14/08 – 16/08
166 €/nighttotal: 332 € (2 )

Park View Place - Apt 1 - Historic Olde Towne

1 2
apartment , Portsmouth
This charming apartment is located in Olde Towne Portsmouth, a historic district just next to Red Lion Park, offering a peaceful retreat within walking distance of the city's attractions. The property enjoys excellent ratings for location, cleanliness, and overall user experience.
The apartment can accommodate up to 3 guests and features a comfortable living space with modern amenities like a smart TV, high-speed Wi-Fi, and a well-equipped kitchen. Guests can enjoy the convenience of air conditioning, parking, and access to a shared common space, making this a perfect choice for families or groups seeking a comfortable and convenient stay in Portsmouth.

Best Chesapeake, VA holiday rentals with parking

Sojourn At Colley Manor Unit 1 Sleeps 4 - Chesapeake, VA
Chesapeake, VA
01/07 – 31/07
143 €/nighttotal: 4290 € (30 )

Sojourn At Colley Manor Unit 1 Sleeps 4

2 2
apartment , Norfolk
Colley Manor Unit 1, a two-bedroom apartment in Norfolk, Virginia, is located 10km from Norfolk International Airport and 10.6km from the Norfolk Botanical Garden.
This 84 square metre self-catering flat sleeps up to six guests and features a fully equipped kitchen, in-unit laundry, free Wi-Fi, and parking, with easy access to Virginia Beach attractions.
Cozy 4 Bed 2 Bath Home - Norfolk, Centrally Located - Chesapeake, VA
9.6 4 reviews
Chesapeake, VA
14/08 – 16/08
349 €/nighttotal: 698 € (2 )

Cozy 4 Bed 2 Bath Home - Norfolk, Centrally Located

4 2
apartment , Norfolk
This four-bedroom house in central Norfolk offers convenient access to downtown attractions and is a short drive from the Virginia Beach oceanfront, with proximity to Town Point Park and the Pagoda and Oriental Garden.
This pet-friendly property accommodates up to eight guests and features a fully equipped kitchen with a microwave oven and dishwasher, air conditioning, parking, and two bathrooms, ensuring a comfortable stay with amenities such as an iron and hair dryer.
Oasis At The Creek - Chesapeake, VA
9.8 14 reviews
Chesapeake, VA
14/08 – 16/08
334 €/nighttotal: 668 € (2 )

Oasis At The Creek

3 2
apartment , Chesapeake
This Chesapeake holiday home is conveniently located near Greenbrier Mall and the Waterside District, offering easy access to Bryant Farms Park and Riverwalk Parkway Park and Playground, though precise distances aren't specified.
The three-bedroom apartment sleeps six guests, boasting a queen, queen, and twin bed configuration, and includes WiFi, a washing machine, air conditioning, and a fully equipped kitchen with a fridge, microwave, and dishwasher.
Steps To Elizabeth River & Dtwn! Portsmouth Condo - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
81 €/nighttotal: 10449 € (129 )

Steps To Elizabeth River & Dtwn! Portsmouth Condo

1 2
apartment , Portsmouth
This one-bedroom flat in Portsmouth is situated 8 minutes' walk from the Portsmouth Naval Shipyard Museum and 6 minutes' walk from the Commodore Theatre.
This 56 square metre apartment accommodates two guests and features a fully equipped kitchen, air conditioning, on-site parking, and internet access, with a coin-operated laundry facility conveniently located nearby.

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

Bright Chesapeake Home Near Shopping And Dining - Chesapeake, VA
10 9 reviews
Chesapeake, VA
23/06 – 25/06
396 €/nighttotal: 792 € (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.
Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
158 €/nighttotal: 20382 € (129 )

Cheerful 2 Bedroom Home Near Virginia Wesleyan

2 2
apartment , Virginia Beach
This private two-bedroom townhome is located on a corner cul-de-sac lot in the Northwest district of Virginia Beach, offering a quiet setting just a short drive to First Landing State Park and the Virginia Aquarium.
This 89 square meter residence accommodates up to four guests, featuring a fully equipped kitchen with a wine cooler, a screened-in porch, an extra-large sectional sofa, and high-speed WiFi, with contactless entry for a seamless self-check-in experience.
Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood. - Chesapeake, VA
Chesapeake, VA
19/07 – 18/10
220 €/nighttotal: 20020 € (91 )

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

1 1
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.
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews
Chesapeake, VA
24/07 – 26/07
421 €/nighttotal: 842 € (2 )

Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8

4 4
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.

Best Chesapeake, VA holiday rentals with air conditioning

Cozy Retreat - Chesapeake, VA
9.7 110 reviews
Chesapeake, VA
24/07 – 26/07
231 €/nighttotal: 462 € (2 )

Cozy Retreat

1 4
apartment , Portsmouth
This Portsmouth apartment at 943 Hamilton Avenue is situated in a peaceful neighbourhood, offering convenient access to various attractions, although precise distances aren't specified.
The two-bedroom, one-bathroom flat sleeps five guests and includes a kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and excellent guest reviews.
Modern Comfort Minutes From Waterside & Downtown - Chesapeake, VA
9.8 12 reviews
Chesapeake, VA
25/09 – 30/09
188 €/nighttotal: 940 € (5 )

Modern Comfort Minutes From Waterside & Downtown

1 4
apartment , Norfolk
This three-bedroom, two-bathroom flat is situated in a quiet Norfolk neighbourhood, just 1.6 kilometres from Downtown Norfolk, the Waterside District, and Norfolk State University.
This accommodation offers parking, air conditioning, and a fully equipped kitchen, with a guest capacity of five people and a back porch for relaxation.
First Class Lvng - 2br, 2ba, Cool/cozy - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
96 €/nighttotal: 12384 € (129 )

First Class Lvng - 2br, 2ba, Cool/cozy

2 2
apartment , Chesapeake
This two-bedroom flat is located in Western Branch North, just 4km from Chesapeake Square Mall and within 10km of Bon Secours Health Center at Harbour View and Riverfront Golf Club. The surrounding area offers a mix of residential and commercial spaces, with easy access to amenities and attractions.
The 93 square metre flat comfortably accommodates up to four guests and features a fully equipped kitchen, two bathrooms, and a washing machine. Guests can enjoy a relaxing atmosphere with a dining area and a TV, and benefit from amenities such as air conditioning, parking, and internet access.
Modern Apartment Stay With Fast Wi-fi And Workspace - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
48 €/nighttotal: 6192 € (129 )

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.
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