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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.

Serene Tree House Retreat | Spacious 1br/1bth Home - Chesapeake, VA
9.9 32 reviews

Serene Tree House Retreat | Spacious 1br/1bth Home

apartment, Chesapeake
This Chesapeake apartment is located in a quiet residential neighborhood, just south of downtown Norfolk and a short drive from Virginia Beach Town Center and the Virginia Beach Boardwalk. The apartment has earned excellent ratings for cleanliness and user experience, and a very good rating for location.
The Magnolia Tree House Charm is a one-bedroom apartment that can accommodate two guests. It offers a variety of amenities, including a private terrace, a fire pit, a grilling area, and a fitness center.
Entire Apartment In Chesapeake, Virginia - Chesapeake, VA
9.8 12 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.
Fully Renovated And Modernized Home In Chesapeake - Chesapeake, VA
10 23 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.
Simply Amazing In Chesapeake - Chesapeake, VA
10 40 reviews

Simply Amazing In Chesapeake

apartment, Chesapeake
This Chesapeake home is conveniently located near shopping, dining, and entertainment options, just a short drive from Virginia Beach and Norfolk. The property has received excellent ratings for cleanliness, location, and overall experience.
This 3-bedroom, 2-bathroom home comfortably sleeps 8 guests. You'll enjoy modern appliances, a fully equipped kitchen, a private garden, and easy access to nearby attractions like the Ocean View boardwalk, Virginia Beach, and Rivers Casino.

Best Chesapeake, VA vacation rentals with air conditioning

Charming 2 Bedroom, 2 Bath Townhome Located In Portsmouth, Simple And Elegant!! - Chesapeake, VA
9.2 30 reviews

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

apartment, Portsmouth
This Portsmouth townhouse, centrally located in Hampton Roads, offers easy access to the Rivers Casino and Virginia Beach Boardwalk, a short drive away.
The 900-square-foot property features two bedrooms with queen-size beds, two bathrooms, and accommodates up to four guests, boasting a fully equipped kitchen, private backyard deck, and amenities including Wi-Fi, air conditioning, and parking.
The Cozy Cottage Two Bedroom, King Bed House - Chesapeake, VA
9.9 139 reviews

The Cozy Cottage Two Bedroom, King Bed House

apartment, Chesapeake
This charming Cape Cod-style house is conveniently located in Chesapeake, just a short drive from the city's attractions and amenities. The property has received excellent ratings for cleanliness, location, and overall user experience.
This cozy home features two bedrooms, a comfortable living area, and a fully equipped kitchen, accommodating up to four guests. Enjoy modern amenities like central air conditioning, smart TVs, and a convenient parking space.
Cowbell Cottage - Chesapeake, VA
9.7 39 reviews

Cowbell Cottage

apartment, Chesapeake
Cowbell Cottage, located in the Chesapeake countryside, offers a peaceful retreat a short drive from Chesapeake City's attractions.
This three-bedroom, one-bathroom house sleeps eight guests and features a full kitchen, air conditioning, internet access, and allows pets.
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.

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
8.0 1 review

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.
A 4-br 2 Bath House In A Well Loved Neighborhood Centrally Located In Portsmouth - Chesapeake, VA
No reviews

A 4-br 2 Bath House In A Well Loved Neighborhood Centrally Located In Portsmouth

apartment, Portsmouth
This non-smoking vacation home in Portsmouth is located near entertainment venues, just a 12-minute drive from Norfolk Scope and Waterside District, and close to a water park and wildlife spotting opportunities.
This 2000 sq ft residence offers 4 bedrooms, 2 bathrooms, and accommodates up to 8 guests with amenities including a full kitchen, air conditioning, complimentary Wi-Fi, a private terrace, and on-site parking.
Historic Olde Towne 2 Bedroom 1 Bath 1100sq Ft Vacation Rental - Chesapeake, VA
9.0 53 reviews

Historic Olde Towne 2 Bedroom 1 Bath 1100sq Ft Vacation Rental

apartment, Portsmouth
This Portsmouth riverfront apartment is a short walk from the Commodore Theatre, Virginia Sports Hall of Fame, and Tidewater Yacht Marina, with the Children's Museum of Virginia and Portsmouth Naval Shipyard Museum within a 15-minute walk.
This two-bedroom, one-bathroom rental sleeps four, features free WiFi, on-site parking, a fully equipped kitchen including a dishwasher, and a terrace – perfect for exploring Portsmouth's attractions.
Boutique Private 2nd Floor 2br Apartment  W/d  Near Casino & Downtown - Chesapeake, VA
No reviews

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

apartment, Portsmouth
This private upstairs apartment in historic Westhaven, Portsmouth, is located 2.5 miles from Rivers Casino Portsmouth and 6.3 miles to downtown Norfolk's Waterside District.
This 650 square foot unit accommodates up to four guests with two bedrooms, one bathroom, a kitchenette, a washer/dryer, and off-street parking.

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.

Waterfront Oasis With Fenced Yard - Chesapeake, VA
9.7 311 reviews

Waterfront Oasis With Fenced Yard

house, Chesapeake
This charming townhouse in Chesapeake offers a peaceful setting with a backyard overlooking a small lake. The property has received excellent ratings for its cleanliness, location, and overall experience.
The home features an open floor plan, accommodating up to 8 guests comfortably. It includes modern amenities such as a fully equipped kitchen, laundry facilities, and air conditioning, ensuring a comfortable and enjoyable stay.
Sojourn | Virginia Beach | 2 Bedroom Townhouse - Chesapeake, VA
No reviews

Sojourn | Virginia Beach | 2 Bedroom Townhouse

apartment, Virginia Beach
This townhome in Virginia Beach's Northwest neighborhood is across from Virginia Wesleyan College, offering convenient access to Naval Air Station Oceana and Sentara Virginia Beach General Hospital within a 5-11 mile radius.
This 2-bedroom, 1-bathroom rental accommodates up to 5 guests and features a fully equipped kitchen with granite countertops, high-speed Wi-Fi, smart TVs with streaming services, and optional baby gear rentals.
Cozy Portsmouth Retreat 2br 1ba - Chesapeake, VA
8.5 10 reviews

Cozy Portsmouth Retreat 2br 1ba

house, Portsmouth
This comfortable house in Portsmouth is conveniently located near Mount Trashmore Park and Virginia Beach National Golf Club, making it ideal for exploring both Portsmouth and Virginia Beach. The house has consistently received excellent ratings for cleanliness and user experience, with guests praising its location and overall comfort.
The 1100 square foot house has two bedrooms and one bathroom, comfortably accommodating up to six guests. The property features a fully equipped kitchen, air conditioning, a private garden, and free Wi-Fi, allowing guests to enjoy a relaxing and enjoyable stay.
Port Peaceful, Backyard, Cozy Beds! Family Ready - Chesapeake, VA
9.6 4 reviews

Port Peaceful, Backyard, Cozy Beds! Family Ready

apartment, Portsmouth
This Portsmouth rental unit is a 5-minute walk from the Portsmouth Naval Shipyard and within a 30-minute drive of Virginia Beach.
This 2-bedroom, 1-bathroom apartment accommodates up to 8 guests, features a fully stocked kitchen, and offers convenient access to Downtown Norfolk and Ocean View Beach.

Best Chesapeake, VA vacation rentals with parking

The Southern Magnolia | 2br/1bth Home - Chesapeake, VA
9.6 11 reviews

The Southern Magnolia | 2br/1bth Home

apartment, Chesapeake
Spacious Chesapeake Home W/ Pool Table! - Chesapeake, VA
9.5 2 reviews

Spacious Chesapeake Home W/ Pool Table!

house, Chesapeake
Free Breakfast. Indoor Pool & Hot Tub. Near The Virginia Beach Business District! - Chesapeake, VA
No reviews

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

apartment, Chesapeake
Stylish Two Bdrm, 1 1/2 Bth, King Bed Townhouse - Chesapeake, VA
9.9 66 reviews

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

apartment, 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.

Contemporary 5 Br 4 Ba Over 3500 Sf Waterfront Direct Access To Chesapeake Bay - Chesapeake, VA
10 3 reviews

Contemporary 5 Br 4 Ba Over 3500 Sf Waterfront Direct Access To Chesapeake Bay

apartment, 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 Mermaids Oasis - Chesapeake, VA
9.7 6 reviews

The Mermaids Oasis

apartment, Virginia Beach
Cozy + Curated 2br Virginia Beach Home With Pool And Sauna - Chesapeake, VA
No reviews

Cozy + Curated 2br Virginia Beach Home With Pool And Sauna

apartment, Virginia Beach
3-bedroom Home Away From Home In Fabulous Chesapeake, Virginia. - Chesapeake, VA
10 54 reviews

3-bedroom Home Away From Home In Fabulous Chesapeake, Virginia.

apartment, Chesapeake
Port Peaceful, Backyard, Cozy Beds! Family Ready - Chesapeake, VA
7.0 2 reviews

Port Peaceful, Backyard, Cozy Beds! Family Ready

apartment, Portsmouth

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.

The Cove House - Chesapeake, VA
9.3 6 reviews

The Cove House

house, Chesapeake
Modern 1 Br Greenbrier Ches - Chesapeake, VA
10 1 review

Modern 1 Br Greenbrier Ches

apartment, Chesapeake
The Royal Palms Retreat Home | Pool | King Bed - Chesapeake, VA
10 2 reviews

The Royal Palms Retreat Home | Pool | King Bed

apartment, Virginia Beach
Lovely Town Home - Chesapeake, VA
9.6 68 reviews

Lovely Town Home

apartment, Virginia Beach

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.

Whispering Woods Estate- Secluded And Spacious - Chesapeake, VA
9.9 33 reviews

Whispering Woods Estate- Secluded And Spacious

apartment, Virginia Beach
Spacious 4br-corporate/military & Medical Stay - Chesapeake, VA
No reviews

Spacious 4br-corporate/military & Medical Stay

apartment, Suffolk
The Manor- Extended Stays - Chesapeake, VA
10 8 reviews

The Manor- Extended Stays

apartment, Chesapeake
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
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