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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.

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.
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.
The Full House - Chesapeake, VA
9.6 80 reviews

The Full House

apartment, Chesapeake
This Chesapeake apartment is located in a quiet neighborhood, just 20 minutes from the Virginia Beach oceanfront, offering easy access to the beach, boardwalk, and other attractions. The apartment has consistently received excellent ratings for user experience, location, and cleanliness.
This 3-bedroom, 2-bathroom home comfortably accommodates up to 6 guests. The apartment offers a full kitchen with a fridge, freezer, microwave, and dishwasher, as well as air conditioning, parking, and internet access.
The Southern Magnolia | 2br/1bth Home - Chesapeake, VA
9.6 11 reviews

The Southern Magnolia | 2br/1bth Home

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.

Best Chesapeake, VA vacation rentals with air conditioning

Estudió Moderno - Chesapeake, VA
9.9 141 reviews

Estudió Moderno

cabin, Virginia Beach
This Virginia Beach apartment rental offers a 1-bedroom, 1-bathroom unit sleeping up to 2 guests and includes amenities such as air conditioning, internet, and parking.
The apartment's precise location within Virginia Beach is unspecified, however, it provides easy access to the city's attractions.
Chesapeake Comfort - Chesapeake, VA
9.3 14 reviews

Chesapeake Comfort

apartment, Chesapeake
This 3-bedroom, 2-bathroom apartment in Chesapeake offers a serene living environment with convenient access to local attractions.
This comfortable residence accommodates up to 6 guests and features air conditioning, internet, a full kitchen with a dishwasher and freezer, and parking.
Cozy First Floor, Two Bedroom, One Bath Apartment. - Chesapeake, VA
9.5 28 reviews

Cozy First Floor, Two Bedroom, One Bath Apartment.

apartment, Portsmouth
This studio apartment at 350 Washington Street, Apartment 2, is located in downtown Portsmouth, VA, one block from Starbucks and two blocks from restaurants, with ferry access to Norfolk every half hour.
This pet-friendly unit accommodates up to four guests and includes internet, a kitchen, air conditioning, and one bathroom, with a provided access code for entry.
Southern Charm
Warm And Welcome - Chesapeake, VA
9.6 90 reviews

Southern Charm Warm And Welcome

apartment, Chesapeake
This Chesapeake apartment is conveniently located near shopping, dining, and the interstate, making it a great option for exploring the area. The apartment has received excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
This rental offers a comfortable space with one bathroom and can accommodate up to four guests. The apartment boasts a fully equipped kitchen, a fenced yard, a fire pit, a gas grill, and a washer and dryer, providing all the comforts of home.

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.

Prime Location In Chesapeake With Spacious 4br & Big Kitchen - Chesapeake, VA
9.5 2 reviews

Prime Location In Chesapeake With Spacious 4br & Big Kitchen

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.
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews

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

apartment, Portsmouth
Located 0.9 miles from Rivers Casino Portsmouth, this house is ideal for travelers seeking a convenient location to explore the city's landmarks. With an excellent user rating, this 3-bedroom, 2-bathroom vacation home is perfect for groups of up to 6 people.
The house boasts a spacious 1000 square feet of floor area, a fully equipped kitchen, and a garden where guests can relax and unwind. Additional amenities include air conditioning, a terrace/balcony, parking, and free WiFi, ensuring a comfortable and enjoyable stay.
Historic Old Towne Southern Charm - Chesapeake, VA
9.4 44 reviews

Historic Old Towne Southern Charm

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.
Centrally Located Hampton Roads Home W/ Game Room! - Chesapeake, VA
No reviews

Centrally Located Hampton Roads Home W/ Game Room!

house, Portsmouth
This house is centrally located in Portsmouth, 10 miles from Norfolk Botanical Garden and 22 miles from the King Neptune Statue on the Boardwalk.
This 2900 square foot home accommodates 15 guests with 4 bedrooms, 3 bathrooms, a full kitchen, air conditioning, and a dedicated game room.

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 Retreat | Optional Guest House Add-on - Chesapeake, VA
9.3 16 reviews

Spacious Retreat | Optional Guest House Add-on

apartment, Portsmouth
This 3-bedroom, 1-bathroom apartment in Portsmouth is located within minutes of the casino and the dining and attractions of Olde Towne.
This pet-friendly rental accommodates up to 6 guests and features a fully stocked kitchen, a large backyard, and a flex room with a 70-inch TV and game table, with an option to rent a separate guesthouse for larger groups.
Shipside Suite~fast Wi-fi, Backyard Oasis, Family - Chesapeake, VA
10 1 review

Shipside Suite~fast Wi-fi, Backyard Oasis, Family

apartment, Portsmouth
This Portsmouth condo is a 3-minute drive from the Children's Museum of Virginia and the Portsmouth Naval Shipyard Museum.
This 950-square-foot residence accommodates up to six guests with two bedrooms, one bathroom, air conditioning, Wi-Fi, a full kitchen, and in-unit laundry, plus a garden with a fire pit and barbecue.
Chesapeake. Comfy  & Cozy. 4 Beds 2 Bath - Chesapeake, VA
9.2 90 reviews

Chesapeake. Comfy & Cozy. 4 Beds 2 Bath

apartment, Chesapeake
This 4-bedroom apartment is located in a peaceful neighborhood in Chesapeake, just minutes from Rivers Casino, Downtown Portsmouth, and Norfolk International Airport. This rental has received excellent ratings for its cleanliness, location, and overall experience.
The apartment is ideal for families or groups of friends, offering ample space for everyone. It features a fully equipped kitchen, a comfortable living area, and a private garden, making it perfect for relaxing and enjoying your stay.
Prime Location In Chesapeake + Spacious 4br + Chef's Kitchen - Chesapeake, VA
9.4 9 reviews

Prime Location In Chesapeake + Spacious 4br + Chef's Kitchen

apartment, Chesapeake
This Chesapeake vacation home is located in the Greenbrier area, offering convenient access to Greenbrier Mall and Waterside District, and is approximately 25 miles from VA Beach.
This 2000 sq ft residence accommodates up to 8 guests with 4 bedrooms and 2 bathrooms, featuring a dedicated movie theater, an updated kitchen, a master suite with a soaking tub, and a well-maintained outdoor yard.

Best Chesapeake, VA vacation rentals with parking

Comfortable & Private 2 Bedrm Cottage W/ King Bed. - Chesapeake, VA
9.2 26 reviews

Comfortable & Private 2 Bedrm Cottage W/ King Bed.

cottage, Portsmouth
The Cozy Cottage Two Bedroom, King Bed House - Chesapeake, VA
9.9 136 reviews

The Cozy Cottage Two Bedroom, King Bed House

apartment, Chesapeake
Oasis At The Creek| Park, Family & Pet Friendly - Chesapeake, VA
9.8 67 reviews

Oasis At The Creek| Park, Family & Pet Friendly

apartment, Chesapeake
Cute Luxurious Home/va Beach! - Chesapeake, VA
10 2 reviews

Cute Luxurious Home/va Beach!

apartment, Virginia Beach

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.

Country Escape - Next Door - Hidden Gem - Chesapeake, VA
10 81 reviews

Country Escape - Next Door - Hidden Gem

house, Chesapeake

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.

Sojourn 2 Bedroom Townhouse In Virginia Beach - Chesapeake, VA
No reviews

Sojourn 2 Bedroom Townhouse In Virginia Beach

apartment, Virginia Beach
Cute 4 Bed 2.5 Bath Home - Sleeps 12! 30 Night Min - Chesapeake, VA
No reviews

Cute 4 Bed 2.5 Bath Home - Sleeps 12! 30 Night Min

apartment, Virginia Beach
Port Peaceful, Backyard, Cozy Beds! Family Ready - Chesapeake, VA
No reviews

Port Peaceful, Backyard, Cozy Beds! Family Ready

apartment, Portsmouth
Modern 3 Bed 2 Bath Cottage - Chesapeake, VA
10 1 review

Modern 3 Bed 2 Bath Cottage

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.

Nyakio Suite - Chesapeake, VA
No reviews

Nyakio Suite

apartment, 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
Experience Timeless Luxury At Cavalier Manor On A Lake - Chesapeake, VA
9.6 10 reviews

Experience Timeless Luxury At Cavalier Manor On A Lake

apartment, Portsmouth
Vb Palm View: Furnished Monthly Rental - Sleeps 12 - Chesapeake, VA
10 15 reviews

Vb Palm View: Furnished Monthly Rental - Sleeps 12

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.

Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth - Chesapeake, VA
8.6 11 reviews

Charming 1-bedroom In-law Suite With Functional Kitchen In Pleasant Portsmouth

apartment, Portsmouth
Condo ∙ 1 Bedroom ∙ 6 Guests - Chesapeake, VA
No reviews

Condo ∙ 1 Bedroom ∙ 6 Guests

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
The Mermaids Oasis - Chesapeake, VA
9.7 6 reviews

The Mermaids Oasis

apartment, Virginia Beach
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