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Chesapeake, VA vacation rentals
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Best Vacation rentals and Airbnb offers in Chesapeake, VA

Top-Rated Vacation Rentals near the City Center in Chesapeake, VA

These vacation rentals in the downtown area of Chesapeake, VA offer unbeatable walking access to vibrant local life, dining, and culture.

Fully Renovated And Modernized Home In Chesapeake - Chesapeake, VA
10 22 reviews

Fully Renovated And Modernized Home In Chesapeake

apartment, Chesapeake
This Chesapeake apartment is located close to Portlock Galleries at SoNo and Greenbrier Mall, offering easy access to art, shopping, and dining. It has received excellent user ratings, making it a popular choice for travelers. The 3-bedroom, 3-bathroom dwelling comfortably accommodates up to 8 guests. Enjoy modern amenities like a smart TV, Wi-Fi, a washer and dryer, a barbecue area, and a sofa bed for extra sleeping space.
The Refresh Experience - Chesapeake, VA
9.2 74 reviews

The Refresh Experience

house, Chesapeake
This Chesapeake house rental boasts two king bedrooms, each with a private bathroom, plus a queen sleeper sofa, comfortably accommodating six guests.
The property includes a fully equipped kitchen with stainless steel appliances, a charcoal grill, smart TVs, high-speed Wi-Fi, and air conditioning.
Entire Apartment In Chesapeake, Virginia - Chesapeake, VA
9.8 8 reviews

Entire Apartment In Chesapeake, Virginia

apartment, Chesapeake
This Chesapeake condo offers prime access, located 2 minutes from I64 and minutes from the Oceanfront, Downtown Norfolk, and Busch Gardens.
This spacious 4-guest apartment features 2 bathrooms, a full kitchen, a private balcony, and a swimming pool, with optional weekly cleaning for longer stays.
Cancun Daze - Chesapeake, VA
8.7 43 reviews

Cancun Daze

house, Chesapeake
This centrally located Chesapeake house offers easy access to area attractions.
The 3-bedroom, 2-bathroom home sleeps 8 guests comfortably, boasting a king master suite, two queen bedrooms, a queen pull-out sofa, and all new LVP flooring; amenities include a fully equipped kitchen, fast Wi-Fi, and TVs in every room.

Best Chesapeake, VA vacation rentals with air conditioning

Condo Near Portsmouth Naval On Webster Avenue - Chesapeake, VA
10 24 reviews

Condo Near Portsmouth Naval On Webster Avenue

apartment, Portsmouth
This Portsmouth apartment rental is conveniently located less than a mile from Portsmouth Naval Hospital and five miles from the Rivers Casino.
The three-bedroom, one-bathroom unit sleeps six guests and includes amenities such as air conditioning, internet, parking, and a full kitchen; enjoy easy access to Portsmouth attractions and the family-friendly neighborhood.
Bright Chesapeake Home Near Shopping & Dining - Chesapeake, VA
9.7 30 reviews

Bright Chesapeake Home Near Shopping & Dining

apartment, Chesapeake
This charming guest house is located in Chesapeake, Virginia, just 26 miles from Virginia Beach, offering easy access to both the city and the beach. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The 2-bedroom, 1-bathroom rental comfortably accommodates up to 4 guests. You'll enjoy a well-equipped kitchen, a relaxing porch, and a Smart TV, as well as a washer and dryer, a hair dryer, and keyless entry for added convenience.
Cozy Condo Near Portsmouth Naval - Chesapeake, VA
9.7 3 reviews

Cozy Condo Near Portsmouth Naval

house, Portsmouth
This 1100 sq ft vacation home in Portsmouth offers convenient access to the Portsmouth Naval Shipyard and is 9.4 miles from Norfolk Botanical Garden.
This 3-bedroom property accommodates up to 10 guests and features air conditioning, a full kitchen with a dishwasher, complimentary WiFi, and free private parking.
Cozy Rambler - 3 Bd 2 Bath Home Full Of Charm - Chesapeake, VA
9.4 88 reviews

Cozy Rambler - 3 Bd 2 Bath Home Full Of Charm

apartment, Portsmouth
This Portsmouth apartment is conveniently located near the city's attractions, making it an ideal base for exploring the area. The apartment consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The spacious home comfortably accommodates up to six guests, offering plenty of room for families or groups. The apartment features modern amenities like a fully equipped kitchen, air conditioning, covered parking, and a backyard, ensuring a comfortable and enjoyable stay.

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.

Popular destinations

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.

Spacious Modern 3-bedroom House In Beautiful Portsmouth City. - Chesapeake, VA
No reviews

Spacious Modern 3-bedroom House In Beautiful Portsmouth City.

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.
4-bedroom House In Beautiful Virginia Beach Downtown - Chesapeake, VA
8.0 9 reviews

4-bedroom House In Beautiful Virginia Beach Downtown

apartment, Virginia Beach
This 4-bedroom, 1-bathroom house in Virginia Beach's Northwest neighborhood offers proximity to the Waterside District, Greenbrier Mall, First Landing State Park, Veterans United Home Loans Amphitheater, and Ocean Breeze Waterpark.
This accommodation accommodates up to 10 guests with a King bed and three Queen beds, featuring air conditioning, heating, and internet for a comfortable stay.
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 Chesapeake apartment is located just a short distance from the Norfolk waterfront and a 20-minute drive from Virginia Beach, offering easy access to both urban amenities and coastal attractions. The surrounding area is peaceful and quiet, perfect for a relaxing getaway.
This one-bedroom, one-bathroom apartment can comfortably accommodate up to four guests. It features free curbside parking, a front porch for enjoying the outdoors, and amenities such as air conditioning, internet access, and a washer and dryer.
Fenced Yard & Patio! 2,400-sq-ft Chesapeake Home - Chesapeake, VA
10 1 review

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

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.

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.

Spacious Home In Chesapeake - Chesapeake, VA
9.5 2 reviews

Spacious Home In Chesapeake

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.
Cambridge Knights A 3 Bedroom Home Full Of Charm - Chesapeake, VA
10 1 review

Cambridge Knights A 3 Bedroom Home Full Of Charm

apartment, Portsmouth
This Portsmouth vacation home is located near the beach, within a 3-mile radius of popular landmarks such as the Commodore Theatre and the Virginia Sports Hall of Fame and Museum. The house offers three bedrooms, two bathrooms, and can accommodate up to six guests.
Amenities include a fully equipped kitchen, multiple bathrooms, laundry facilities, free WiFi, a Smart TV, a smoke-free environment, parking, and a spa.
The Retreat House - Chesapeake, VA
9.7 62 reviews

The Retreat House

house, Virginia Beach
This 3-bedroom, 2-bathroom townhouse is located near Regent University in Virginia Beach, close to the oceanfront and Sandbridge Beach, making it a convenient base for exploring the city. The property has received excellent ratings for its cleanliness, location, and overall experience.
The townhouse features an open-concept living area, perfect for families or groups of up to 8 guests. The fully equipped kitchen, spacious backyard with outdoor seating and a barbecue grill, and additional bedding options ensure a comfortable and enjoyable stay.
The Manor- Extended Stays - Chesapeake, VA
10 5 reviews

The Manor- Extended Stays

apartment, Chesapeake
This Chesapeake apartment rental is conveniently located near Greenbrier Mall, offering easy access to the Oceanfront, Norfolk Waterside, and various local attractions like the Chesapeake Jubilee and Deep Creek Locks.
This spacious 4-bedroom, 2-bathroom unit sleeps 8, features a remodeled kitchen with updated appliances, a 65-inch flat-screen TV, free Wi-Fi, and self check-in via keypad.

Best Chesapeake, VA vacation rentals with parking

Instant Serenity-just Add Water - Chesapeake, VA
No reviews

Instant Serenity-just Add Water

boat, Portsmouth
Cozy And Comfy Ranch Style Home. - Chesapeake, VA
9.6 37 reviews

Cozy And Comfy Ranch Style Home.

apartment, Portsmouth
Serene & Intimate Home| Near Casino + Pet Friendly - Chesapeake, VA
9.7 59 reviews

Serene & Intimate Home| Near Casino + Pet Friendly

apartment, Portsmouth
3 Bd Townhome Near Historic Waterfront Portsmouth - Chesapeake, VA
9.3 110 reviews

3 Bd Townhome Near Historic Waterfront Portsmouth

house, Portsmouth

Find the Best Luxury Vacation Rentals in Chesapeake, VA

Discover ultimate relaxation in a luxury Chesapeake, VA vacation rental, where comfort meets a central, prime location.

Cozy House In Portsmouth - Chesapeake, VA
9.3 8 reviews

Cozy House In Portsmouth

house, Portsmouth

Discover Pet-Friendly Vacation Rentals in Chesapeake, VA

Experience a pet-friendly stay in Chesapeake, VA with vacation rentals located steps away from city dog parks and walking trails.

The Cozy Dominion Suite In Chesapeake - Chesapeake, VA
8.5 83 reviews

The Cozy Dominion Suite In Chesapeake

apartment, Chesapeake
#2 Rent Green In Ghent (Flexible Dates) - Chesapeake, VA
9.4 62 reviews

#2 Rent Green In Ghent (Flexible Dates)

apartment, Norfolk
Premium Comfort Home - Chesapeake, VA
9.2 18 reviews

Premium Comfort Home

apartment, Chesapeake
Beautiful Home In Chesapeake - Chesapeake, VA
10 25 reviews

Beautiful Home In Chesapeake

apartment, Chesapeake

Top-Rated Vacation Rentals with a Pool in Chesapeake, VA

Choose a Chesapeake, VA rental with a pool for a refreshing swim right in the heart of the city.

Neon Wonderland, Sleeps 14, Hot Tub/pool/mini Golf - Chesapeake, VA
10 4 reviews

Neon Wonderland, Sleeps 14, Hot Tub/pool/mini Golf

apartment, Portsmouth
Free Breakfast. Indoor Pool & Hot Tub. Close To The Virginia Beach Business District! - Chesapeake, VA
8.0 4 reviews

Free Breakfast. Indoor Pool & Hot Tub. Close To The Virginia Beach Business District!

apartment, Chesapeake
Cavalier Manor: Pool, Luxury Home, & Scenic Views - Chesapeake, VA
9.7 75 reviews

Cavalier Manor: Pool, Luxury Home, & Scenic Views

apartment, Portsmouth
Waterfront Oasis: Fishing Pier, Pool, Beach Access - Chesapeake, VA
10 8 reviews

Waterfront Oasis: Fishing Pier, Pool, Beach Access

house, Chesapeake

Top Vacation Rentals with a Hot Tub in Chesapeake, VA

Unwind after a day of urban exploration with a private hot tub at your own vacation rental in Chesapeake, VA.

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great For Business Travelers! - Chesapeake, VA
No reviews

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great For Business Travelers!

apartment, Chesapeake
Condo ∙ 2 Bedrooms ∙ 6 Guests - Chesapeake, VA
No reviews

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Chesapeake
Wooded Wonderland - Chesapeake, VA
9.6 15 reviews

Wooded Wonderland

apartment, Portsmouth
Gorgeous 1 Bedroom With Free Wifi & Street Parking - Chesapeake, VA
8.0 1 review

Gorgeous 1 Bedroom With Free Wifi & Street Parking

apartment, Chesapeake
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