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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.
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 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

Water View 1 Bed 1 Bath Retreat - Chesapeake, VA
9.8 32 reviews

Water View 1 Bed 1 Bath Retreat

apartment, Portsmouth
This cozy Portsmouth cottage, situated on the Elizabeth River near Bon Secours Maryview Medical Center, offers waterfront views and easy access to major hospitals, military bases, and downtown.
The one-bedroom, one-bathroom rental sleeps two, features a full kitchen with dishwasher, in-unit laundry, a private garden with a propane grill and tree swing, and includes free off-street parking.
Blissful Nook @ Washington - Chesapeake, VA
10 122 reviews

Blissful Nook @ Washington

apartment, Chesapeake
This Chesapeake apartment rental, located above a garage on the second floor, offers convenient access to Virginia Beach, the Outer Banks, Colonial Williamsburg, Busch Gardens, and Water Country USA, though precise distances are not specified.
The one-bedroom unit features a king-size bed, walk-in closet, full kitchen with stainless steel appliances (including a fridge, freezer, microwave, and dishwasher), private entrance with digital lock, and accommodates two guests.
Modern 2 Bdrm Home W/firepit, Game Console, Bikes - Chesapeake, VA
9.6 71 reviews

Modern 2 Bdrm Home W/firepit, Game Console, Bikes

apartment, Portsmouth
This Portsmouth vacation rental boasts convenient access to the 41-mile Seaboard Coastline Trail, perfect for exploring the Hampton Roads area.
The fully renovated house features two bedrooms, one bathroom, sleeps six (with an extra guest fee), includes a complete kitchen with dishwasher, a fenced backyard with a fire pit, and provides bikes for guests, all within a pet-friendly environment.
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.

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.
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.
Bright Chesapeake Home Near Shopping & Dining - Chesapeake, VA
9.2 11 reviews

Bright Chesapeake Home Near Shopping & Dining

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.
Charming 1-bedroom 1-bath Unit With Beautiful Riverfront Sunsets In Portsmouth - Chesapeake, VA
9.8 9 reviews

Charming 1-bedroom 1-bath Unit With Beautiful Riverfront Sunsets In Portsmouth

apartment, Portsmouth
This waterfront Portsmouth apartment boasts a prime location near Bon Secours Maryview Medical Center, the Naval Medical Center Portsmouth, and downtown, offering easy access to beaches and the Waterside District.
The one-bedroom, one-bathroom rental features a full kitchen with dishwasher, in-unit laundry, two smart TVs, a private tree swing overlooking the Elizabeth River, and accommodates two guests; free off-street parking is also provided.

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.

Virginia Beach Townhome - Chesapeake, VA
9.4 111 reviews

Virginia Beach Townhome

house, Virginia Beach
This 2-bedroom townhome in Virginia Beach is just 20 minutes from the Oceanfront, making it a convenient base for exploring the city's attractions. The house has consistently received excellent ratings for cleanliness, location, and overall guest experience.
The townhome comfortably accommodates up to 8 guests and features a fully equipped kitchen, washer and dryer, spacious parking, and access to owner-provided games and beach items. Guests can enjoy a relaxing garden and take advantage of the nearby beach and other attractions.
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.
Condo ∙ 1 Bedroom ∙ 6 Guests - Chesapeake, VA
No reviews

Condo ∙ 1 Bedroom ∙ 6 Guests

apartment, Chesapeake
Located in Chesapeake, Virginia, within a 25-minute drive of the Virginia Beach oceanfront, this 1 Bedroom Suite offers a convenient and comfortable stay for travelers visiting Chesapeake. The apartment features a modern and comfortable interior design, with a fully-equipped kitchen and air-conditioned living space. It can accommodate up to 6 guests and has 1 bedroom and 1 bathroom.
The apartment includes amenities such as free Wi-Fi, cable television, a DVD player, a washer and dryer, and complimentary parking. Guests can also enjoy access to an indoor pool, hot tub, complimentary breakfast buffet, 24-hour business and fitness centers, and evening receptions with food and drinks.
Portsmouth 3br Near Casino | Spacious Yard Stay - Chesapeake, VA
9.5 63 reviews

Portsmouth 3br Near Casino | Spacious Yard Stay

apartment, Portsmouth
This Portsmouth home is conveniently located within a 5-minute drive of the highway and close to downtown Portsmouth, Norfolk, Virginia Beach, and Chesapeake. The property has received excellent ratings for cleanliness and location, making it a great choice for travelers looking for a comfortable and convenient stay.
This 3-bedroom, 2-bathroom house comfortably sleeps 6 guests and features a spacious open-concept living area. Enjoy modern amenities like a fully equipped kitchen, washer and dryer, WiFi, and 4 TVs, along with a large fenced-in backyard with a patio and gas grill for outdoor gatherings.

Best Chesapeake, VA vacation rentals with parking

11 Mi To Virginia Beach Boardwalk: Studio Retreat! - Chesapeake, VA
8.0 3 reviews

11 Mi To Virginia Beach Boardwalk: Studio Retreat!

studio, Virginia Beach
Spacious 5 Bedroom W/ Pool And Patio Area. - Chesapeake, VA
10 3 reviews

Spacious 5 Bedroom W/ Pool And Patio Area.

apartment, Chesapeake
A Touch Of Historic Olde Town - Chesapeake, VA
9.4 68 reviews

A Touch Of Historic Olde Town

apartment, Portsmouth
Cozy Portsmouth Getaway 2br/1ba - Chesapeake, VA
9.5 35 reviews

Cozy Portsmouth Getaway 2br/1ba

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.

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

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.

First Class Lvng - 2br, 2ba, Cool/cozy - Chesapeake, VA
No reviews

First Class Lvng - 2br, 2ba, Cool/cozy

apartment, Chesapeake
Waterfront Oasis: Fishing Pier, Pool, Beach Access - Chesapeake, VA
10 13 reviews

Waterfront Oasis: Fishing Pier, Pool, Beach Access

house, Chesapeake
Waterfront Home Near Va Beach | Sleeps 16+ | 5br - Chesapeake, VA
10 2 reviews

Waterfront Home Near Va Beach | Sleeps 16+ | 5br

apartment, Norfolk
Rustic Downtown Living - 1br/1.5ba - Chesapeake, VA
9.9 33 reviews

Rustic Downtown Living - 1br/1.5ba

apartment, Norfolk

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.

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
The Cove House - Chesapeake, VA
9.3 6 reviews

The Cove House

house, Chesapeake
Elegance Escape On Saunders Dr - Chesapeake, VA
9.7 62 reviews

Elegance Escape On Saunders Dr

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

Whispering Woods Estate- Secluded And Spacious

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.

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

The Manor- Extended Stays

apartment, Chesapeake
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
The Mermaids Oasis - Chesapeake, VA
9.7 6 reviews

The Mermaids Oasis

apartment, Virginia Beach
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
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