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

Portsmouth 3br Near Casino | Spacious Yard Stay - Chesapeake, VA
9.5 66 reviews

Portsmouth 3br Near Casino | Spacious Yard Stay

apartment, Portsmouth
This Portsmouth house is ideally situated just a short drive from the new Rivers Casino and within easy reach of downtown Portsmouth, Norfolk, Virginia Beach, and Chesapeake. The accommodation has received excellent ratings for cleanliness and location, and is rated very good overall.
The house has 3 bedrooms and 2 bathrooms, comfortably sleeping 6 guests. It features modern amenities like a kitchen with a fridge and microwave, a washer and dryer, high-speed Wi-Fi, multiple TVs with streaming services, a large fenced backyard with a patio, furniture, and a gas grill, and security features like exterior cameras and an ADT security system.
Spacious 5-bedroom House With Ac In Beautiful Portsmouth - Chesapeake, VA
8.8 6 reviews

Spacious 5-bedroom House With Ac In Beautiful Portsmouth

apartment, Portsmouth
This five-bedroom house in Portsmouth, VA, is located in the central district of Historic Downtown, offering proximity to shops, restaurants, cultural attractions, and the waterfront, with the Hill House Museum and United States Lightship Portsmouth within walking distance.
This spacious property accommodates up to 18 guests with five bedrooms, three bathrooms, a fully equipped kitchen with a dishwasher, air conditioning, garden, spa, and on-site parking, making it ideal for larger groups seeking self-catering options near MacArthur Center and the Waterside District.
The Chesapeake Gray  Historical Waterside District 20 Mins To Oceanfront - Chesapeake, VA
9.4 8 reviews

The Chesapeake Gray Historical Waterside District 20 Mins To Oceanfront

apartment, Norfolk
This Norfolk apartment is located within easy reach of both Waterside Festival Marketplace and Virginia Beach Town Center, offering a convenient base for exploring the city and its surroundings. The apartment is just a short drive from the beach, providing a perfect blend of urban convenience and coastal charm.
The property is a spacious three-bedroom home that comfortably sleeps six guests. It offers a modern kitchen, a private backyard with a patio, and a jacuzzi, ideal for relaxing after a day of exploring the local attractions.
The Birds Nest - Chesapeake, VA
9.8 65 reviews

The Birds Nest

apartment, Chesapeake
This apartment is located in the Great Bridge area of Chesapeake, just 32 kilometres from the oceanfront, 8 kilometres from the interstate, and 10 kilometres from Greenbriar Mall, offering a peaceful retreat with a country feel despite its proximity to urban amenities. The property has received excellent ratings for location, cleanliness, and user experience.
The self-catering property can accommodate up to 8 guests and boasts a spacious outdoor area with a large fenced yard and an open field. It also features a tree house, a gazebo with an extension cord for lighting, and a variety of amenities including a Jacuzzi, a garden, and parking.

Best Chesapeake, VA holiday rentals with parking

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).
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.
Centrally Located Hampton Roads Home W/ Game Room! - Chesapeake, VA
10 1 review

Centrally Located Hampton Roads Home W/ Game Room!

apartment, Portsmouth
This family and pet-friendly flat in Portsmouth offers convenient access, situated 4 kilometres from Downtown Norfolk and 33 kilometres from First Landing State Park.
This 269 square metre residence accommodates up to 8 guests across 4 bedrooms and 3 bathrooms, featuring a game room with a pool table and arcade games, a fenced garden with a deck, patio, and fire pit, a dry bar, record player, and a well-equipped kitchen.
Home With Historic Charm! Close To Naval Hospital! - Chesapeake, VA
9.5 4 reviews

Home With Historic Charm! Close To Naval Hospital!

apartment, Portsmouth
This Portsmouth apartment is situated in a quiet historic district, less than 1.6km from the Naval Medical Center Portsmouth and within 8km of several major Norfolk medical centres, including Sentara Norfolk General Hospital.
The three-bedroom, two-bathroom property sleeps five guests and boasts excellent amenities including air conditioning, parking, and internet access; nearby attractions include the Portsmouth waterfront and its restaurants.

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. You'll find fewer crowds and more affordable rates during these months. The weather is still pleasant, and you can enjoy all the attractions without the summer rush.
  • What are the best Airbnb and holiday rentals in Chesapeake, VA?

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

    The Chesapeake Bay Trail is a popular walking and cycling route that stretches along the Chesapeake Bay waterfront. The Great Bridge Battlefield and Waterways History Trail is another good option, offering a scenic route through the historic Great Bridge area. For a shorter walk, try the Chesapeake Arboretum's nature trails.
  • What are the most popular Airbnbs in Chesapeake, VA?

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

    The Chesapeake Arboretum is pet-friendly, and you can bring your furry friend along for a walk on the trails. The Chesapeake Bay Maritime Museum also welcomes well-behaved dogs on a leash.
  • 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 top sports attractions and facilities in Chesapeake, VA?

    The Chesapeake Regional Healthcare YMCA offers a variety of fitness classes, swimming pools, and sports courts. The Chesapeake City Park has tennis courts, baseball fields, and a playground. For golf enthusiasts, the Chesapeake Golf Club offers a challenging 18-hole course.
  • 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 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.

Popular destinations

Best Chesapeake, VA holiday rentals with a balcony

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.
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.
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.
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.

Best Chesapeake, VA holiday rentals with air conditioning

Harbor Haven Retreat - Chesapeake, VA
9.6 18 reviews

Harbor Haven Retreat

apartment, Portsmouth
This spacious Portsmouth, Virginia house is centrally located in the historic downtown area, within walking distance of shops and restaurants, and a short drive (distances unspecified) from local beaches and the Portsmouth Casino.
Sleeping up to 15 guests in five bedrooms and three bathrooms, this fully equipped property boasts a kitchen with fridge, microwave, dishwasher and washer/dryer, air conditioning, a garden, parking, and excellent guest reviews.
Tidewater Treasurer - Chesapeake, VA
10 1 review

Tidewater Treasurer

apartment, Portsmouth
This 3-bedroom flat in Portsmouth offers a prime central location in Tidewater, providing easy access to the beach, the casino, and numerous attractions within 5 kilometres.
This well-equipped accommodation for up to 8 guests features air conditioning, a garden, and a kitchen with a fridge, freezer, microwave, and dishwasher, ensuring a comfortable stay with internet provided.
Charming 1-bedroom 1-bath Unit With Beautiful Riverfront Sunsets In Portsmouth - Chesapeake, VA
9.8 9 reviews

Charming 1-bedroom 1-bath Unit With Beautiful Riverfront Sunsets In Portsmouth

apartment, Portsmouth
This Portsmouth waterfront apartment, situated near Bon Secours Maryview Hospital (within 8km), offers easy access to the city's naval bases and the Waterside District.
The one-bedroom flat sleeps two, includes a full kitchen with dishwasher, in-unit laundry, smart TVs, a terrace, and free off-street parking, plus nearby access to a tree swing and shared porch.
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).
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