Search vacation rentals in Chesapeake, VA from 100+ sites!

677 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Chesapeake, VA vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Chesapeake, VA

Compare Vacation Rentals for Families in Chesapeake, VA

These kid-friendly vacation rentals in Chesapeake, VA keep you close to top city attractions for a stress-free family vacation.

Private 1 Bed Apt - Historic Olde Towne Portsmouth - Chesapeake, VA
10 3 reviews
Chesapeake, VA
08/09 – 08/28
$99/nighttotal: $1881 (19 )

Private 1 Bed Apt - Historic Olde Towne Portsmouth

1 2
apartment , Portsmouth
This Portsmouth, Virginia apartment is centrally located downtown, within walking distance of the historic downtown district, eight minutes from the new Rivers Casino Portsmouth, and a 30-minute drive from Virginia Beach.
This one-bedroom, one-bathroom rental sleeps two guests and features a fully equipped kitchen with a fridge, microwave, dishwasher, air fryer, and cast iron skillet, plus air conditioning and free Wi-Fi.
Vb Palm View: Furnished Monthly Rental - Sleeps 12 - Chesapeake, VA
10 15 reviews
Chesapeake, VA
08/01 – 08/31
$241/nighttotal: $7230 (30 )

Vb Palm View: Furnished Monthly Rental - Sleeps 12

1 6
apartment , Virginia Beach
This spacious Virginia Beach house, near Mount Trashmore and Town Center, offers easy access to the Virginia Beach Oceanfront (15 minutes away) and Norfolk Naval Shipyard (20 minutes away).
The 4-bedroom, 6-bed, 2.5-bathroom home sleeps up to 12 guests and includes a private above-ground pool (open April-September), a fully equipped kitchen with an air fryer and slow cooker, free Wi-Fi, and parking for four cars.
Fast Wifi! King! Tree House Bed! Arcade! Smrt Tvs - Chesapeake, VA
9.7 187 reviews
Chesapeake, VA
08/09 – 08/28
$222/nighttotal: $4218 (19 )

Fast Wifi! King! Tree House Bed! Arcade! Smrt Tvs

2 2
house , Virginia Beach
This two-bedroom townhouse is located in Virginia Beach, just a short distance from the Amphitheater, Farmers Market, Mall, and Restaurants, and 15 minutes from the oceanfront. The property consistently receives excellent ratings for cleanliness, location, and user experience.
The Virginia Beach townhouse comfortably accommodates up to 5 guests. It features a fully equipped kitchen, air conditioning, a garden, parking, and family-friendly amenities like a treehouse-style bunk bed and a classic arcade game system.
Comfortable 3 Bedroom House With Deck With Hot Tub - Chesapeake, VA
9.7 116 reviews
Chesapeake, VA
07/09 – 07/14
$527/nighttotal: $2635 (5 )

Comfortable 3 Bedroom House With Deck With Hot Tub

1 5
house , Virginia Beach
This 3-bedroom house is located in the quiet Kings Forest neighborhood, just a short distance from the beach and Virginia Beach's town center. The property has received excellent ratings for user experience, location, and cleanliness.
This home comfortably sleeps 7 guests and features a modern kitchen with a fridge, microwave, and dishwasher. Enjoy amenities like a hot tub, a private yard, high-speed Wi-Fi, and a 48" Samsung smart TV.

Best Chesapeake, VA vacation rentals with parking

Fenced Yard & Patio! 2,400-sq-ft Chesapeake Home - Chesapeake, VA
10 1 review
Chesapeake, VA
08/09 – 08/28
$576/nighttotal: $10944 (19 )

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

4 2
house , Chesapeake
This Chesapeake vacation rental is conveniently located just 10 miles from Norfolk, offering easy access to attractions like Norfolk Botanical Garden and the King Neptune Statue on the Boardwalk. The home is situated in a quiet residential area, providing a peaceful retreat from the hustle and bustle of the city.
This spacious 4-bedroom home comfortably accommodates up to 15 guests, featuring a fully equipped kitchen with modern appliances like a dishwasher and oven. Enjoy the outdoor dining area, relax on the patio, or take a dip in the spa.
Quiet 4br House — Comfortable & Convenient - Chesapeake, VA
9.5 125 reviews
Chesapeake, VA
07/10 – 07/12
$304/nighttotal: $608 (2 )

Quiet 4br House — Comfortable & Convenient

1 1
house , Portsmouth
This newly renovated 4-bedroom house is located in Portsmouth, Virginia, a 25-minute drive from Virginia Beach and 5 minutes from the new Rivers Casino. It has excellent user, location, and cleanliness ratings.
The house has over 1200 square feet of living space, 4 spacious bedrooms with full-size beds, 2 bathrooms, and a private backyard. It also has central AC, ceiling fans, cable, Wi-Fi, flat-screen TVs with streaming services, and a full kitchen with a fridge, freezer, microwave oven, and dishwasher.
Newly Updated Private Studio - Chesapeake, VA
10 1 review
Chesapeake, VA
08/09 – 08/28
$167/nighttotal: $3173 (19 )

Newly Updated Private Studio

1 2
studio , Portsmouth
This studio apartment in Portsmouth's Churchland district is conveniently located a short drive from attractions like the Waterside Festival Marketplace and Hampton Coliseum, offering a peaceful retreat in a quiet residential area. The studio consistently receives excellent guest ratings, reflecting its comfortable accommodations and convenient location.
The studio features a single bedroom and bathroom, accommodating up to four guests. Enjoy amenities like air conditioning, Wi-Fi, a television, a fully equipped kitchen, laundry facilities, and access to a private garden and barbecue facilities for outdoor relaxation.
The Point! Private Waterfront  Oasis! - Chesapeake, VA
9.9 126 reviews
Chesapeake, VA
07/10 – 07/12
$1133/nighttotal: $2266 (2 )

The Point! Private Waterfront Oasis!

1 1
apartment , Norfolk
This Norfolk vacation home, near Virginia Beach, offers easy access to Oceanview Beach, Downtown Norfolk, Rivers Casino, and the Waterside District, providing a convenient base for exploring the area. This four-bedroom, two-bathroom house comfortably sleeps ten guests and boasts a fully equipped kitchen, fitness center, and private garden with breathtaking views, plus amenities like air conditioning, a dishwasher, and free internet access.

Frequently Asked Questions about vacation rentals in Chesapeake, VA

  • What are the top family-friendly attractions in Chesapeake, VA?

    The Chesapeake Arboretum is a great place to spend an afternoon with the kids, with its nature trails, playground, and educational exhibits. The Chesapeake Children's Museum is another excellent option for families with younger children, offering interactive exhibits and play areas. And for some outdoor fun, the Chesapeake City Park has a playground, picnic areas, and a splash pad.
  • What are the best Airbnb and vacation rentals in Chesapeake, VA?

    King Guest Suite - A Togar Vacation Rental, Townhome In Convient Location and Modern Luxury Peace & Quiet are the most popular Airbnb and vacation rentals in Chesapeake, VA among travelers.

  • 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, spring (April-May) and fall (September-October), when the weather is pleasant and the crowds are smaller. You'll also find better deals on rental prices during these months.
  • What are the most popular Airbnbs in Chesapeake, VA?

  • What events or festivals should visitors check out in and around Chesapeake, VA?

    The Chesapeake Bay Wine Festival in May is a popular event featuring wine tastings, live music, and food vendors. The Chesapeake Bay Seafood Festival in October is another great option, offering seafood dishes, live entertainment, and family-friendly activities. For a unique experience, check out the Great Dismal Swamp Festival in June, celebrating the history and culture of the swamp.
  • 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 restaurants with local dishes in Chesapeake, VA?

    For fresh seafood, try The Black Eyed Pea, known for its Chesapeake Bay crab cakes. For a taste of Southern comfort food, head to The Chesapeake Inn, famous for its fried chicken and hushpuppies. If you're looking for something a little more upscale, The Waterside Restaurant offers a refined dining experience with stunning waterfront views.
  • 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 a leisurely walk or bike ride, offering scenic views of the bay and the city. For a more challenging ride, try the Dismal Swamp Canal Trail, a paved path that winds through the Great Dismal Swamp. You can also explore the city's parks and neighborhoods on foot, discovering hidden gems and local attractions.
  • 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, Chesapeake has a number of pet-friendly attractions. The Chesapeake Bay Trail is dog-friendly, and many of the city's parks allow dogs on leash. You can also find pet-friendly restaurants and hotels throughout the city. The Chesapeake Arboretum is a great option for a walk with your furry friend.
  • What are the benefits of choosing a vacation rental in Chesapeake, VA?

    Vacation rentals offer more space and privacy than hotels, often with amenities like a full kitchen and laundry facilities. They can also be a more affordable option, especially for families or groups traveling together. You'll also have the flexibility to cook your own meals and enjoy a more relaxed atmosphere.
  • 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 facilities. You can also catch a baseball game at the Harbor Park Stadium, home to the Norfolk Tides, a minor league baseball team. For a more casual experience, check out the city's many parks and playgrounds for outdoor recreation.

Destinations nearby

Choose the Right Vacation Rentals with a Terrace in Chesapeake, VA

Start your morning right with a vacation rental in Chesapeake, VA featuring a private balcony and stunning views.

Historic Old Towne Southern Charm - Chesapeake, VA
9.6 35 reviews
Chesapeake, VA
09/17 – 09/28
$147/nighttotal: $1617 (11 )

Historic Old Towne Southern Charm

2 5
apartment , Portsmouth
This charming 18th-century home is situated in Old Towne Portsmouth, a short walk from downtown restaurants, shops, and museums. It's a quiet area, perfect for a relaxing getaway. The apartment has consistently received very good ratings from guests.
This two-bedroom, two-bathroom apartment can comfortably accommodate up to seven guests. Amenities include a fully equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a terrace or balcony, a garden, and internet access.
Bright Chesapeake Home Near Shopping & Dining - Chesapeake, VA
10 9 reviews
Chesapeake, VA
08/25 – 09/07
$385/nighttotal: $5005 (13 )

Bright Chesapeake Home Near Shopping & Dining

2 2
house , Chesapeake
This Chesapeake vacation home is conveniently located within 15 miles of Topgolf Virginia Beach and 19 miles from Mount Trashmore Park, offering easy access to entertainment and outdoor activities. The home consistently receives excellent ratings for location, cleanliness, and user experience, making it a top choice for travelers.
This 2-bedroom, 1-bathroom home comfortably accommodates up to 4 guests and offers 1000 square feet of living space. Enjoy modern amenities like free WiFi, a cable flat-screen TV, a washing machine, and a fully equipped kitchen, along with a relaxing patio and access to a spa.
Spacious Home In Chesapeake - Chesapeake, VA
9.5 2 reviews
Chesapeake, VA
09/17 – 09/28
$394/nighttotal: $4334 (11 )

Spacious Home In Chesapeake

4 5
house , Chesapeake
This spacious Chesapeake, Virginia home is conveniently located approximately 7.5 miles from the Norfolk Botanical Garden, 17 miles from the Neptune Statue, and 5.4 miles from Topgolf Virginia Beach.
This 2,000-square-foot house features four bedrooms, three bathrooms, and can comfortably accommodate up to 14 guests, offering free Wi-Fi, a fully equipped kitchen, private parking, and a terrace.
Spacious Modern 3-bedroom House In Beautiful Portsmouth City. - Chesapeake, VA
Chesapeake, VA
08/01 – 08/31
$598/nighttotal: $17940 (30 )

Spacious Modern 3-bedroom House In Beautiful Portsmouth City.

3 6
apartment , Portsmouth
This 4-bedroom, 3-bathroom apartment in Portsmouth is a 7-minute drive to Town Point Park and a 20-minute drive to Chesapeake Bay, with the Children's Museum of Virginia and Portsmouth Naval Shipyard Museum just 3 minutes away. This unit offers Wi-Fi, air conditioning, a smart TV, laundry facilities, a sunroom, and parking for up to 6 guests, with a check-out time of 11:00 AM.

Best Chesapeake, VA vacation rentals with air conditioning

A Touch Of Historic Olde Town - Chesapeake, VA
9.3 58 reviews
Chesapeake, VA
09/17 – 09/28
$173/nighttotal: $1903 (11 )

A Touch Of Historic Olde Town

1 5
apartment , Portsmouth
This Old Town Portsmouth apartment is conveniently located near the Elizabeth River Walk, Portsmouth Naval Hospital, and High Street's restaurants and bars.
This three-bedroom, two-bathroom rental sleeps six guests and features a fully equipped kitchen with a refrigerator, air conditioning, and free internet access.
The Southern Magnolia | 2br/1bth Home - Chesapeake, VA
9.8 9 reviews
Chesapeake, VA
08/25 – 09/07
$181/nighttotal: $2353 (13 )

The Southern Magnolia | 2br/1bth Home

1 2
apartment , Chesapeake
This Chesapeake apartment is conveniently located just south of downtown Norfolk, within a short drive of Virginia Beach Town Center and the Boardwalk. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The two-bedroom, one-bathroom apartment comfortably accommodates up to four guests. The apartment offers a well-equipped kitchen, private waterfront access with a shared terrace, and a cozy screened-in porch overlooking a 200-year-old Magnolia Tree.
The Hideaway, A Super Cozy Cottage In Portsmouth - Chesapeake, VA
9.3 15 reviews
Chesapeake, VA
06/29 – 08/03
$82/nighttotal: $2870 (35 )

The Hideaway, A Super Cozy Cottage In Portsmouth

1 2
apartment , Portsmouth
This Portsmouth apartment is located near Scott's Creek, just a mile and a half from the historic downtown area and waterfront. The two-bedroom apartment comfortably accommodates three guests and offers amenities such as a kitchen, air conditioning, parking, and internet access.
Stylish Two Bdrm, 1 1/2 Bth, King Bed Townhouse - Chesapeake, VA
9.9 57 reviews
Chesapeake, VA
06/26 – 06/28
$265/nighttotal: $530 (2 )

Stylish Two Bdrm, 1 1/2 Bth, King Bed Townhouse

1 1
apartment , Portsmouth
This two-bedroom apartment is located less than a mile from the Rivers Casino in Portsmouth, offering easy access to the city's attractions and amenities. Guests consistently rate this apartment as excellent for its cleanliness, location, and overall experience.
The apartment comfortably accommodates up to four guests and features a modern kitchen equipped with a fridge, freezer, microwave, and dishwasher. Enjoy the convenience of air conditioning, a private garden, and parking, all while being close to the casino for entertainment and dining options.
©2026 cozycozy.com