Compare Vacation Rentals & Airbnb in Chesapeake, VA

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Chesapeake, VA vacation rentals
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939 Rentals and Airbnb in Chesapeake, VA

Best family friendly Chesapeake, VA vacation rentals

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

Spacious Chesapeake Home W/ Pool Table! - Chesapeake, VA
No reviews

Spacious Chesapeake Home W/ Pool Table!

house, Chesapeake
Vacation rental. You will be based in Chesapeake.
Services and facilities include a kitchen, an iron and a fridge. This house also has air conditioning!
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.
A Quiet Lakeside Home For Family, Business, Or Both To Relax Or Be Productive. - Chesapeake, VA
8.4 25 reviews

A Quiet Lakeside Home For Family, Business, Or Both To Relax Or Be Productive.

apartment, Virginia Beach
This four-bedroom, three-bathroom house in Virginia Beach is situated in a quiet cul-de-sac, approximately 48km from the beach, 27km from Naval Station Norfolk (NOB), and 19km from Naval Air Station Oceana.
The property, sleeping eight guests, offers a dedicated office space, lake views, and amenities including coffee, soap, and laundry pods; nearby attractions include the Veterans United Home Loans Amphitheatre and Greenbrier Mall.
Waterfront Oasis: Fishing Pier, Pool, Beach Access - Chesapeake, VA
10 13 reviews

Waterfront Oasis: Fishing Pier, Pool, Beach Access

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.

Best Chesapeake, VA vacation rentals with parking

Nyakio Suite - Chesapeake - Chesapeake, VA
No reviews

Nyakio Suite - Chesapeake

apartment, Chesapeake
This two-bedroom flat is located in Chesapeake's Greenbrier district, a 7-minute walk from Rivercrest Play Area and a 10-minute walk from Dominion Marketplace.
This 101 square metre residence accommodates up to four guests, featuring a fully equipped kitchen, air conditioning, Wi-Fi, a balcony, and access to an on-site swimming pool and parking.
Private Boutique Apt W/d Near Casino & Downtown - Chesapeake, VA
9.8 27 reviews

Private Boutique Apt W/d Near Casino & Downtown

apartment, Portsmouth
This Westhaven flat is situated in Portsmouth, offering historic character and convenient access to Rivers Casino, NNSY, and Naval Station Norfolk, all within a few kilometres.
This two-bedroom residence accommodates up to four guests and includes a kitchenette, air conditioning, private parking, and an in-unit washer/dryer for a comfortable stay.
First Class Lvng - 2br, 2ba, Cool/cozy - Chesapeake, VA
9.0 2 reviews

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

apartment, Chesapeake
This apartment is conveniently located in Chesapeake, Virginia, just 1.5km from RTE 664, offering easy access to local hospitals, military bases, and downtown Norfolk, which is a 24km drive away. The nearest hospital is a mere 6km away.
The apartment has two bedrooms and two bathrooms, comfortably accommodating up to four guests. It features a well-equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a garden, and parking.
Historic Haven - Chesapeake, VA
9.8 55 reviews

Historic Haven

house, Portsmouth
This two-bedroom flat is situated in a prime location in Portsmouth, just a short walk from the historic Naval Shipyard Museum and close to the charming shops and restaurants of the Olde Towne district. The apartment is highly rated for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The flat is ideal for families or groups of up to 5 people, offering a comfortable and convenient base for exploring the city. It features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning and parking.

Frequently Asked Questions about vacation 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 avoid the crowds and enjoy pleasant weather, with temperatures ranging from 15 to 25 degrees Celsius.
  • What are the best Airbnb and vacation rentals in Chesapeake, VA?

    King Guest Suite - A Togar Vacation Rental, Townhome In Convient Location and Econo Lodge Chesapeake Route 13 And I-464 are the most popular Airbnb and vacation rentals in Chesapeake, VA among travelers.

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

    Take a walk or bike ride along the Chesapeake Bay Trail, a scenic trail that stretches for over 160 km. You can also visit the Chesapeake Arboretum, a beautiful green space with free admission. And if you're looking for a fun and affordable way to spend an evening, check out the Chesapeake Farmers Market, held every Saturday from May to October.
  • What are the most popular Airbnbs in Chesapeake, VA?

  • What are the best restaurants with local dishes in Chesapeake, VA?

    For a taste of Chesapeake's local seafood, try The Crab Pot, a popular spot known for its fresh blue crabs and other seafood dishes. Another great option is The Chesapeake Inn, a waterfront restaurant serving classic Chesapeake Bay dishes like crab cakes and oyster stew.
  • What are the best vacation rentals with a pool in Chesapeake, VA?

    Modern Condo In Western Branch, The Peaceful Oasis and Cheshire Retreat are the best vacation rentals with a pool in Chesapeake, VA.

  • 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, offering scenic views of the Chesapeake Bay and its tributaries. You can also explore the Chesapeake Arboretum, which has a network of walking trails and a beautiful garden.
  • 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.

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

    Yes, there are plenty of pet-friendly attractions in Chesapeake. The Chesapeake Arboretum welcomes dogs on leash, and the Chesapeake Bay Foundation's Brock Environmental Center has a dog-friendly outdoor area. Many restaurants also have outdoor seating areas that are pet-friendly.
  • 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.

  • What are the benefits of choosing a vacation rental in Chesapeake, VA?

    Vacation rentals offer more space and privacy than hotels, and they often come with amenities like kitchens and laundry facilities. They can also be more affordable, especially for families or groups. Plus, you'll have the chance to experience life like a local, with access to neighbourhood amenities and a more authentic experience.
  • What are the top sports attractions and facilities in Chesapeake, VA?

    The Chesapeake Sportsplex is a popular destination for sports enthusiasts, with a variety of fields and courts for baseball, softball, soccer, and more. The Chesapeake YMCA also offers a range of sports activities and facilities, including a swimming pool, gym, and fitness classes.

Popular destinations

Best Chesapeake, VA vacation rentals with a balcony

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

Bright Chesapeake Home Near Shopping & Dining

house, Chesapeake
Book this vacation rental. You will be located in Chesapeake.
Services and facilities include free parking, a terrace and a kitchen. Take advantage of the air conditioning in this house in Chesapeake.
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.
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.
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.

Best Chesapeake, VA vacation rentals with air conditioning

The Cove House - Chesapeake, VA
9.3 6 reviews

The Cove House

house, Chesapeake
This 4-bedroom, 2-bathroom flat in Chesapeake offers ample space for families, situated in a district convenient for local attractions and family-friendly activities.
This accommodation, ideal for up to 10 guests, features air conditioning, a fully equipped kitchen with a fridge, microwave, and dishwasher, and on-site amenities including a swimming pool, garden, fitness centre, and parking.
Spacious 5 Bedroom W/ Pool And Patio Area. - Chesapeake, VA
10 3 reviews

Spacious 5 Bedroom W/ Pool And Patio Area.

apartment, Chesapeake
This four-bedroom house is centrally located in the Chesapeake district, providing convenient access to local attractions and amenities.
This spacious property accommodates up to eight guests and features a private swimming pool and a fitness centre, offering a comfortable and well-equipped base for your stay in Chesapeake.
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.
Portsmouth 2br/1ba Getaway - Chesapeake, VA
10 2 reviews

Portsmouth 2br/1ba Getaway

apartment, Portsmouth
This Portsmouth holiday home is situated within 4.8km of attractions including the Commodore Theatre, the Virginia Sports Hall of Fame and Museum, and the Children's Museum of Virginia.
The 102 square metre property sleeps six guests and boasts two bedrooms, one bathroom, a fully equipped kitchen, garden, parking, and a smoke-free environment.
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