Holiday Rentals in Chesapeake, VA

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Chesapeake, VA holiday rentals
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939 Holiday rentals and Airbnb in Chesapeake, VA

Best family friendly Chesapeake, VA holiday rentals

Among the 939 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals

Cozy Portsmouth Retreat 2br 1ba - Chesapeake, VA
8.6 11 reviews

Cozy Portsmouth Retreat 2br 1ba

house, Portsmouth
This charming house in Portsmouth is conveniently located just 14 km from Mount Trashmore Park, 20 km from Virginia Beach National Golf Club, and 11 km from Topgolf Virginia Beach, making it easy to explore the area's attractions. The property has received excellent user ratings for cleanliness and is situated in a good location.
The house spans 102 square metres and comfortably accommodates up to 6 guests in its two bedrooms and one bathroom. It features a fully equipped kitchen, a washing machine, air conditioning, a garden, and free Wi-Fi, ensuring a relaxing and comfortable stay.
Elegance Escape On Saunders Dr - Chesapeake, VA
9.7 62 reviews

Elegance Escape On Saunders Dr

apartment, Portsmouth
This 3-bedroom holiday home is conveniently situated just a short walk from Portsmouth City Park and Elizabeth Manor Golf and Country Club, offering easy access to both relaxation and recreation.
The apartment comfortably sleeps 6 guests, with three bedrooms, a living room, and a dedicated entertainment area. Enjoy the spacious outdoor areas, including a patio, a front porch, a fire pit, and two grills, as well as a fully equipped kitchen and a swimming pool (open from May 25th to September 15th).
3br, 6 Beds  Prime Stay Near Rivers Casino! - Chesapeake, VA
10 2 reviews

3br, 6 Beds Prime Stay Near Rivers Casino!

apartment, Portsmouth
This Portsmouth holiday home is situated within 5km of the Rivers Casino Portsmouth, the Commodore Theatre, and the Virginia Sports Hall of Fame, offering easy access to these attractions.
The three-bedroom property sleeps six guests and boasts a fully equipped kitchen with appliances including a dishwasher, a garden, parking, and free Wi-Fi, alongside a washing machine and barbecue facilities.
Sojourn | Virginia Beach | 2 Bedroom Townhouse - Chesapeake, VA
No reviews

Sojourn | Virginia Beach | 2 Bedroom Townhouse

apartment, Virginia Beach
This two-bedroom Virginia Beach apartment, ideal for families, offers convenient access to local shops and restaurants, its precise location undisclosed but within easy reach of Virginia Beach's attractions.
Sleeping five, the property boasts a fully equipped kitchen with dishwasher, a queen and full-size bed, Hulu Live and Netflix, plus parking and central air conditioning, with a pack 'n' play and high chair available for a fee (pre-booking essential).

Best Chesapeake, VA holiday rentals with parking

Waterfront Oasis With Fenced Yard - Chesapeake, VA
9.7 311 reviews

Waterfront Oasis With Fenced Yard

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.
Nyakio Suite - Chesapeake, VA
No reviews

Nyakio Suite

apartment, Chesapeake
This Nyakio Suite flat is situated on the first floor in a quiet family district of Chesapeake, Virginia, offering a tranquil retreat.
This pet-friendly residence accommodates up to four guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a decorative fireplace, and a private balcony overlooking a seasonal shared swimming pool, with internet and laundry facilities available.
Virginia Beach, Getaway - Chesapeake, VA
9.9 67 reviews

Virginia Beach, Getaway

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.
Cornick Corner Near "Rivers Casino" - Chesapeake, VA
9.8 43 reviews

Cornick Corner Near "Rivers Casino"

apartment, Portsmouth
This Portsmouth bungalow, situated in a quiet residential neighbourhood, is 40km from Virginia Beach and 11km from the Rivers Casino.
The self-catering property sleeps four guests in three bedrooms, one bathroom, and boasts a fully equipped kitchen, including dishwasher, free Wi-Fi, and private parking; note there are four stairs to access the single-family ranch-style home.

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.

Popular destinations

Best Chesapeake, VA holiday rentals with a balcony

Bright Chesapeake Home Near Shopping & Dining - Chesapeake, VA
No reviews

Bright Chesapeake Home Near Shopping & Dining

house, Chesapeake
Holiday house rental. Your accommodation will be located in Chesapeake.
Facilities and services include a terrace, an iron and free parking. This house in Chesapeake also has air conditioning!
Spacious Modern 3-bedroom House In Beautiful Portsmouth City. - Chesapeake, VA
8.0 1 review

Spacious Modern 3-bedroom House In Beautiful Portsmouth City.

apartment, Portsmouth
This four-bedroom, three-bathroom flat in Portsmouth is conveniently located 5.6 kilometres from Town Point Park and 16.1 kilometres from Chesapeake Bay, with the Children's Museum of Virginia and Portsmouth Naval Shipyard Museum a mere 2.4 kilometres away.
Guests can enjoy complimentary Wi-Fi, air conditioning, and on-site laundry facilities in this accommodation, which also features a sunroom or lanai and offers parking for up to six people.
Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
10 1 review

Cheerful 2 Bedroom Home Near Virginia Wesleyan

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.
Bright Chesapeake Home Near Shopping & Dining - Chesapeake, VA
9.2 11 reviews

Bright Chesapeake Home Near Shopping & Dining

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.

Best Chesapeake, VA holiday rentals with air conditioning

Bright Chesapeake Home Near Shopping & Dining - Chesapeake, VA
9.7 32 reviews

Bright Chesapeake Home Near Shopping & Dining

house, Chesapeake
This charming guest house is located in Chesapeake, just 42 kilometres from Virginia Beach, offering easy access to both the city and the nearby coastline. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The self-contained accommodation sleeps up to four guests and features a well-equipped kitchen, a private outdoor space, and modern amenities such as a Smart TV and free Wi-Fi. Guests can enjoy a covered porch, a private entrance, and the convenience of a washer and dryer.
Nyakio Suite - Chesapeake, VA
No reviews

Nyakio Suite

apartment, Chesapeake
The Nyakio Suite is a 2-bedroom flat in Chesapeake, located 17.7 to 33.8 kilometres from Topgolf Virginia Beach, Mount Trashmore Park, and the King Neptune Statue on the Boardwalk.
This 102 square metre residence offers air conditioning, free WiFi, a fully equipped kitchen with a dishwasher and microwave, and can accommodate up to 7 guests, with a private swimming pool available for use.
Old Towne Charm - Chesapeake, VA
9.4 75 reviews

Old Towne Charm

apartment, Portsmouth
This Portsmouth apartment, situated in a historic neighbourhood a 1.6km walk from local pubs and the Naval Medical Center Portsmouth, offers easy access to Norfolk (16km away).
The second-floor, three-bedroom, two-bathroom flat sleeps six, features a fully equipped kitchen (including fridge and microwave), air conditioning, parking, a fitness centre, and excellent guest reviews; nearby attractions include Portsmouth Historic District.
Unique 1 Bedroom Apartment In Bridgeport - Chesapeake, VA
10 32 reviews

Unique 1 Bedroom Apartment In Bridgeport

apartment, Suffolk
This Suffolk apartment is located in the Bridgeport community, just a short walk from the 3800 Acqua amenities, offering access to a fitness centre, clubhouse, and seasonal pool. It enjoys excellent user, location, and cleanliness ratings.
The apartment has a modern, sleek design and can accommodate up to two guests. It features a full kitchen, a private balcony, reserved parking, and a quiet environment despite being above a car wash.
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