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

Modern Luxury Peace & Quiet. - Chesapeake, VA
10 190 reviews

Modern Luxury Peace & Quiet.

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.
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.
Simply Amazing In Chesapeake - Chesapeake, VA
10 40 reviews

Simply Amazing In Chesapeake

house, Chesapeake
This Chesapeake property is conveniently located just 5-10 kilometres from Greenbrier Mall, various shopping plazas, and restaurants, making it a great base for exploring the area. It also enjoys a prime position, being only 15 kilometres from the Virginia Beach oceanfront and 10 kilometres from Ocean View in Norfolk. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
This spacious home offers three bedrooms and two bathrooms, comfortably accommodating up to eight guests. The fully equipped kitchen features a fridge, freezer, microwave, and dishwasher, alongside a garden, parking, air conditioning, and internet access, ensuring a comfortable and enjoyable stay.
Spacious Chesapeake Home W/ Pool Table! - Chesapeake, VA
8.4 15 reviews

Spacious Chesapeake Home W/ Pool Table!

apartment, Chesapeake
This 4-bedroom Chesapeake holiday home is situated in Western Branch North, just a short distance from Chesapeake Square Mall and a drive from Portsmouth City Park and the Chesapeake Arboretum. It has received very good ratings from previous guests.
The property offers 223 square metres of space, accommodating up to 8 guests, with 4 bedrooms and 3 bathrooms. It features a range of amenities, including a private yard, a deck, a pool table, a jetted tub, smart TVs, a fireplace, a washer and dryer, and free Wi-Fi.

Best Chesapeake, VA holiday rentals with parking

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.
"The Ponderosa B" - Close To The Casino & Concerts - Chesapeake, VA
9.8 159 reviews

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

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.
Townhome Style 2br Villa Apt By 4 Major Hospitals - Chesapeake, VA
10 1 review

Townhome Style 2br Villa Apt By 4 Major Hospitals

apartment, Chesapeake
This two-bedroom flat in Chesapeake offers convenient access to four major hospitals within a 3.2 to 11.3 kilometre radius, making it ideal for visiting medical professionals or patients on extended stays.
This residence features a recently updated kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, and a capacity for four guests, with on-site laundry facilities and enhanced security for your comfort and safety.
Beautiful 3bdrm Near Beach, Wi-fi & Parking - Chesapeake, VA
9.8 153 reviews

Beautiful 3bdrm Near Beach, Wi-fi & Parking

apartment, Virginia Beach
This three-bedroom home is situated just 7.5 kilometres from Virginia Beach Oceanfront and 2 kilometres from Town Center, offering a convenient location for exploring the area. The property consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The apartment comfortably accommodates up to six guests and is fully furnished with modern amenities like a dishwasher, air conditioning, and a 55-inch flat-screen TV. Guests can enjoy a range of entertainment options, including foosball, board games, Netflix, and Hulu, as well as unique experiences like private paint parties, crabbing excursions, and paddle board rentals.

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

Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood. - Chesapeake, VA
No reviews

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

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 & 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.
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews

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

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.
A 4-br 2 Bath House In A Well Loved Neighborhood Centrally Located In Portsmouth - Chesapeake, VA
No reviews

A 4-br 2 Bath House In A Well Loved Neighborhood Centrally Located In Portsmouth

apartment, Portsmouth
This spacious four-bedroom flat in Portsmouth is situated conveniently for recreational parks and attractions, a mere 1.9 kilometres from the Norfolk Scope and Waterside District.
Offering 186 square metres of living space for up to eight guests, this residence features a private terrace, air conditioning, complimentary Wi-Fi, and a fully equipped kitchen, with on-site parking also provided.

Best Chesapeake, VA holiday rentals with air conditioning

Contractors Welcomed Spacious Home Sleeps 8 - Chesapeake, VA
9.2 122 reviews

Contractors Welcomed Spacious Home Sleeps 8

house, Portsmouth
This Portsmouth apartment, ideally situated near the Waterside District and a short drive (11-42km) from attractions such as Rivers Casino, Ocean View Beach, and Norfolk International Airport, offers convenient access to Portsmouth's key landmarks.
This four-bedroom, two-bathroom dwelling sleeps eight guests and boasts amenities including a fully equipped kitchen with dishwasher, air conditioning, parking, multiple TVs, and flexible check-in/check-out times (4 pm/10 am).
Centrally Located Hampton Roads Home W/ Game Room! - Chesapeake, VA
No reviews

Centrally Located Hampton Roads Home W/ Game Room!

house, Portsmouth
This centrally located Hampton Roads detached house in Portsmouth offers easy access to attractions, situated 16 kilometres from Norfolk Botanical Garden and 35 kilometres from the King Neptune Statue on the Boardwalk.
This spacious 269 square metre property provides accommodation for up to 15 guests across four bedrooms, featuring a fully equipped kitchen, three bathrooms, air conditioning, a patio, a game room, and complimentary WiFi, with parking and a garden available.
Near Casino, Va Beach, Large Yard,  Quite Relaxing - Chesapeake, VA
9.7 75 reviews

Near Casino, Va Beach, Large Yard, Quite Relaxing

house, Portsmouth
This Portsmouth apartment is conveniently located just 5.6 kilometres from the Norfolk Waterside District, 3.2 kilometres from Roger Browns and 5.6 kilometres from Rivers Casino, all while being situated in a peaceful neighbourhood. The apartment has received excellent ratings for location, cleanliness, and user experience.
The property features two separate suites, offering ample space for up to 7 guests. Amenities include a fully equipped kitchen, laundry facilities, a garden with patio furniture, a fitness centre and secure access with a keypad.
Cozy Portsmouth Retreat 2br/1ba - Chesapeake, VA
9.6 51 reviews

Cozy Portsmouth Retreat 2br/1ba

apartment, Portsmouth
This two-bedroom house, situated in Portsmouth's Port Norfolk Historic District, offers convenient access to local attractions; precise distances would depend on the exact location within the district.
The property sleeps six, features a well-equipped kitchen with a fridge and microwave, and includes amenities such as air conditioning, Wi-Fi, and parking; a lovely backyard provides additional space.
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