Compare Vacation Rentals & Airbnb in Chesapeake, VA

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

Best family friendly Chesapeake, VA vacation rentals

Among the 677 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals

Oasis At The Creek| Park, Family & Pet Friendly - Chesapeake, VA
9.8 63 reviews
Chesapeake, VA
25/09 – 30/09
$374/nighttotal: $1870 (5 )

Oasis At The Creek| Park, Family & Pet Friendly

1 4
apartment , Chesapeake
This three-bedroom house in Deep Creek, Chesapeake, is situated approximately 40km from the local airport and under 8km from restaurants and entertainment.
The self-catering property sleeps six, boasting a fully equipped kitchen with dishwasher, a garden, ample parking, TVs, washer/dryer, fireplace, gas grill, and a fully accessible backyard.
Convenient To All 7 Cities - Chesapeake, VA
9.2 52 reviews
Chesapeake, VA
24/07 – 26/07
$641/nighttotal: $1282 (2 )

Convenient To All 7 Cities

1 4
apartment , Chesapeake
This comfortable home in Chesapeake is conveniently located just a short distance from the Norfolk Waterside District, Rivers Casino, and Sentara/Obici Hospitals, making it a great base for exploring the area. It has received excellent ratings for location, cleanliness, and overall experience.
The house is spacious, with 176 square metres of living space and can accommodate up to six guests in its three bedrooms. It offers a fully equipped kitchen, a relaxing deck, and a private garden, perfect for enjoying a peaceful stay.
Cozy Portsmouth Retreat 2br 1ba - Chesapeake, VA
9.8 7 reviews
Chesapeake, VA
31/07 – 31/08
$263/nighttotal: $8153 (31 )

Cozy Portsmouth Retreat 2br 1ba

2 2
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.
Spacious 5-bedroom House With Ac In Beautiful Portsmouth - Chesapeake, VA
8.0 2 reviews
Chesapeake, VA
12/10 – 18/02
$799/nighttotal: $103071 (129 )

Spacious 5-bedroom House With Ac In Beautiful Portsmouth

5 2
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.

Best Chesapeake, VA vacation rentals with parking

Boutique Private 2nd Floor 2br Apartment  W/d  Near Casino & Downtown - Chesapeake, VA
Chesapeake, VA
25/09 – 30/09
$220/nighttotal: $1100 (5 )

Boutique Private 2nd Floor 2br Apartment W/d Near Casino & Downtown

2 4
apartment , Portsmouth
This private upstairs flat in historic Westhaven, Portsmouth, is conveniently located 4 kilometres from Rivers Casino, 2 kilometres from Portsmouth City Park, and offers proximity to the Commodore Theatre and Portsmouth Naval Shipyard Museum.
This two-bedroom apartment accommodates up to four guests, featuring a kitchenette, a full-size washer and dryer, air conditioning, internet, and private off-street parking for one vehicle.
Charming 2 Bedroom, 2 Bath Townhome Located In Portsmouth, Simple And Elegant!! - Chesapeake, VA
9.2 28 reviews
Chesapeake, VA
24/07 – 26/07
$526/nighttotal: $1052 (2 )

Charming 2 Bedroom, 2 Bath Townhome Located In Portsmouth, Simple And Elegant!!

2 4
apartment , Portsmouth
This Portsmouth townhouse, centrally located in Hampton Roads, offers easy access to the Rivers Casino (distance unspecified) and Virginia Beach Boardwalk (driving distance unspecified).
The 84-square-metre (904 sq ft) property sleeps four guests in two bedrooms with queen-size beds and smart TVs, and includes a fully equipped kitchen, private garden, parking, and excellent Wi-Fi.
Lakefront | Sunset Views | Great Central Location! - Chesapeake, VA
10 1 review
Chesapeake, VA
19/07 – 18/10
$151/nighttotal: $13741 (91 )

Lakefront | Sunset Views | Great Central Location!

2 1
house , Chesapeake
This Chesapeake lakeside townhouse, situated near the Virginia Beach border, offers easy access to both cities and their attractions.
The two-bedroom, two-bathroom property sleeps four guests and includes a fully equipped kitchen, smart TVs, private deck with sunset views, and amenities such as a washer/dryer and parking for two vehicles.
Waterfront Oasis With Fenced Yard - Chesapeake, VA
9.7 295 reviews
Chesapeake, VA
16/08 – 27/08
$357/nighttotal: $3927 (11 )

Waterfront Oasis With Fenced Yard

1 4
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.

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.

Destinations nearby

Best Chesapeake, VA vacation rentals with a balcony

Lovely Town Home - Chesapeake, VA
9.6 68 reviews
Chesapeake, VA
19/07 – 18/10
$324/nighttotal: $29484 (91 )

Lovely Town Home

4 1
apartment , Virginia Beach
This Virginia Beach house is located just 1.8 kilometres from Mount Trashmore Park, offering a peaceful escape from the city bustle, yet remaining within easy reach of the Virginia Beach Town Center and the Sandler Center for the Performing Arts. The property enjoys excellent guest ratings, highlighting its appeal for travellers.
This spacious home has four bedrooms and two bathrooms, comfortably accommodating up to ten guests. The house offers a range of amenities including a swimming pool, a jacuzzi, a garden, a terrace and parking, making it ideal for a relaxing and enjoyable stay.
Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood. - Chesapeake, VA
Chesapeake, VA
29/06 – 03/08
$397/nighttotal: $13895 (35 )

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

1 2
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.
Fenced Yard & Patio! 2,400-sq-ft Chesapeake Home - Chesapeake, VA
10 1 review
Chesapeake, VA
25/09 – 30/09
$897/nighttotal: $4485 (5 )

Fenced Yard & Patio! 2,400-sq-ft Chesapeake Home

4 4
house , Chesapeake
This Chesapeake holiday home, situated 16km from Norfolk, offers easy access to attractions such as the Norfolk Botanical Garden (27km) and the King Neptune Statue (45km).
The 223 square metre property boasts four bedrooms, three bathrooms, sleeps fifteen guests, and includes a fully equipped kitchen, Wi-Fi, air conditioning, a garden, a spa, and on-site parking.
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews
Chesapeake, VA
23/06 – 25/06
$521/nighttotal: $1042 (2 )

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

4 3
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 vacation rentals with air conditioning

Condo ∙ 1 Bedroom ∙ 6 Guests - Chesapeake, VA
Chesapeake, VA
16/08 – 27/08
$292/nighttotal: $3212 (11 )

Condo ∙ 1 Bedroom ∙ 6 Guests

1 4
apartment , Chesapeake
This apartment is conveniently located near the Virginia Beach business district and General Dynamics in Chesapeake, a 40-kilometre drive from the Virginia Beach oceanfront. The surrounding area offers easy access to both business and leisure activities, making it a popular choice for travellers.
This one-bedroom apartment can accommodate up to six guests comfortably, with two queen beds and a sofa bed. Guests can enjoy a range of amenities, including a fully equipped kitchen, a swimming pool, a hot tub, a fitness centre, and free parking.
Simply Amazing In Chesapeake - Chesapeake, VA
9.9 38 reviews
Chesapeake, VA
25/09 – 30/09
$510/nighttotal: $2550 (5 )

Simply Amazing In Chesapeake

1 4
apartment , 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.
The Southern Magnolia | 2br/1bth Home - Chesapeake, VA
9.8 9 reviews
Chesapeake, VA
01/07 – 31/07
$205/nighttotal: $6150 (30 )

The Southern Magnolia | 2br/1bth Home

1 2
apartment , Chesapeake
This Chesapeake apartment, situated in a quiet residential neighbourhood near Highway 464, offers easy access to Norfolk city centre (16km), Greenbrier Mall (8km), and various hospitals within an 8-13km radius.
The ground-floor, fully furnished flat comprises two bedrooms, one bathroom, and accommodates up to four guests, boasting a private screened porch overlooking a 200-year-old Magnolia tree and waterfront views, plus access to a shared waterfront terrace with a fire pit and grilling area; in-unit laundry, a fully equipped kitchen, and reserved parking are also included.
Historic Haven - Chesapeake, VA
9.8 52 reviews
Chesapeake, VA
24/07 – 26/07
$512/nighttotal: $1024 (2 )

Historic Haven

1 4
apartment , 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.
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