Vacation Rentals in Chesapeake, VA

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Chesapeake, VA holiday rentals
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939 Holiday rentals and Airbnb in Chesapeake, VA

Outstanding Family Holiday Rentals in Chesapeake, VA

Compare family holiday rentals in Chesapeake, VA with space and amenities for all.

15 Minutes To The Beach Bungalow - Chesapeake, VA
9.2 62 reviews

15 Minutes To The Beach Bungalow

apartment, Norfolk
This Norfolk holiday home, perfect for families, is situated in [Insert Precise Location, e.g., the village of Burnham Market, 10km from the Norfolk Coast and 20km from Sandringham House].
Sleeping eight guests across three bedrooms and two bathrooms, this self-catering property boasts a fully equipped kitchen, including a dishwasher, air conditioning, a garden, and ample parking.
Virginia Beach Townhome - Chesapeake, VA
9.4 111 reviews

Virginia Beach Townhome

house, Virginia Beach
This townhome is located in Virginia Beach, just 20 kilometres from the Oceanfront, offering a peaceful retreat away from the hustle and bustle. The property has consistently received excellent ratings for its cleanliness, location, and overall user experience.
This two-bedroom, two-bathroom home comfortably accommodates up to eight guests. The property comes equipped with a full kitchen, washer and dryer, free parking, beach gear, games, and toys, making it ideal for families and groups seeking a comfortable and enjoyable stay.
Spacious Chesapeake Home W/ Pool Table! - Chesapeake, VA
8.4 15 reviews

Spacious Chesapeake Home W/ Pool Table!

apartment, Chesapeake
This 4-bedroom Chesapeake holiday home is situated in Western Branch North, just a short distance from Chesapeake Square Mall and a drive from Portsmouth City Park and the Chesapeake Arboretum. It has received very good ratings from previous guests.
The property offers 223 square metres of space, accommodating up to 8 guests, with 4 bedrooms and 3 bathrooms. It features a range of amenities, including a private yard, a deck, a pool table, a jetted tub, smart TVs, a fireplace, a washer and dryer, and free Wi-Fi.
Whispering Woods Estate- Secluded And Spacious - Chesapeake, VA
9.9 33 reviews

Whispering Woods Estate- Secluded And Spacious

apartment, Virginia Beach
This three-storey house is situated in a rural area of Virginia Beach, just 4 km from the Sportsplex, PAAC, and the Amphitheatre, and within easy reach of beaches, shops, restaurants, and breweries. It has received excellent ratings for location, cleanliness, and user experience.
The property sleeps up to 15 guests and is well-equipped with a spacious living room, large kitchen, multiple dining areas, and a screened-in porch. Guests can enjoy swimming in the pool, fishing in the ponds, relaxing in the gardens, or simply enjoying the peaceful atmosphere.

Best Chesapeake, VA holiday rentals with parking

Waterfront Maryview/naval Hosp Casino Close To All - Chesapeake, VA
9.6 292 reviews

Waterfront Maryview/naval Hosp Casino Close To All

apartment, Portsmouth
This apartment is situated on the Elizabeth River in a peaceful, upscale neighbourhood of Portsmouth, offering easy access to the city's attractions and the waterfront. It has received excellent ratings for its cleanliness, location, and overall experience.
The apartment has three bedrooms and one bathroom, accommodating up to eight guests. It features a modern kitchen with granite countertops and stainless steel appliances, a spacious living area, and a private mother-in-law suite with its own entrance, along with a large garden, parking, and Wi-Fi access.
Family Comfort - Chesapeake, VA
9.0 6 reviews

Family Comfort

apartment, Portsmouth
This two-bedroom flat in a quiet Portsmouth district offers a peaceful base, conveniently located for exploring the city's attractions.
This family-friendly apartment accommodates up to four guests and includes essential amenities such as air conditioning, internet, and a kitchen with a fridge, freezer, and microwave oven.
Tasha's Townhouse *King, Queen, Twin* - Chesapeake, VA
9.7 246 reviews

Tasha's Townhouse *King, Queen, Twin*

house, Chesapeake
This house is located in the Greenbrier area of Chesapeake, within easy walking distance of a park, lake, restaurants, and shops. It has received excellent ratings for location, cleanliness, and user experience.
The house has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes with a fully equipped kitchen, air conditioning, a garden, parking, and a Ring Doorbell camera for added security.
The Cozy Dominion Suite In Chesapeake - Chesapeake, VA
8.4 90 reviews

The Cozy Dominion Suite In Chesapeake

apartment, Chesapeake
This Chesapeake condo, situated near shops and restaurants with Downtown Norfolk a 16km drive away, offers convenient access to local amenities and city attractions.
The one-bedroom, one-bathroom apartment sleeps three, featuring a queen-size bed, fully equipped kitchen with dishwasher, smart TV, super-fast WiFi, and a Ring Doorbell for added security; parking is also provided.

Frequently asked questions about holiday rentals in Chesapeake, VA

  • 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, from April to May and September to October. The weather is still pleasant, but the crowds are smaller and prices are often lower. The summer months, June to August, are popular with tourists, so expect higher prices and larger crowds.
  • What are the best Airbnb and holiday rentals in Chesapeake, VA?

  • What are the best budget-friendly activities in Chesapeake, VA?

    Chesapeake offers many budget-friendly activities, including a visit to the Chesapeake Arboretum, exploring the Chesapeake Bay waterfront, or taking a walk or bike ride on the Chesapeake Bay Trail. You can also enjoy a picnic lunch at the Chesapeake City Park or spend an afternoon browsing the shops and restaurants in the Greenbrier area.
  • What are the most popular Airbnbs in Chesapeake, VA?

  • What are the best restaurants with local dishes in Chesapeake, VA?

    For a taste of local seafood, try the Chesapeake Bay Bridge-Tunnel Seafood Restaurant. If you prefer something a bit more casual, try the Chesapeake Bay Brewing Company, which offers a range of craft beers and pub grub. For a more upscale dining experience, try the Chesapeake Inn, which offers a fine-dining menu with a focus on fresh, local ingredients.
  • What are the best holiday rentals with a pool in Chesapeake, VA?

    Modern Condo In Western Branch, The Peaceful Oasis and Cheshire Retreat are the best holiday rentals with a pool in Chesapeake, VA.

  • What are the best walking or cycling routes in Chesapeake, VA?

    The Chesapeake Bay Trail is a popular choice for walking and cycling, offering scenic views of the Chesapeake Bay. The trail is over 160km long and runs through various parts of the city, including the Chesapeake Arboretum and the Chesapeake City Park. For a shorter walk, you can explore the trails at the Chesapeake Arboretum or the Chesapeake Botanical Gardens.
  • 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.

  • Are there pet-friendly attractions in Chesapeake, VA?

    Yes, Chesapeake is a pet-friendly city. The Chesapeake Arboretum welcomes dogs on leash, and the Chesapeake City Park has a dedicated dog park. Many restaurants also have outdoor seating where you can bring your furry friend.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesapeake, VA?

    The best holiday 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.

  • What are the benefits of choosing a vacation rental in Chesapeake, VA?

    Vacation rentals offer a more spacious and comfortable alternative to hotels. They are often located in residential areas, which can provide a more authentic experience of the city. They also offer more privacy and flexibility than traditional accommodations, allowing you to prepare your own meals and set your own schedule.
  • What are the top sports attractions and facilities in Chesapeake, VA?

    Chesapeake is home to the Chesapeake Regional Healthcare YMCA, which offers a range of fitness and sports facilities, including a swimming pool, a gymnasium, and a fitness centre. For outdoor activities, the Chesapeake City Park offers a variety of sports facilities, including baseball fields, tennis courts, and a skate park.

Popular destinations

Top-Rated Holiday Rentals with a Balcony in Chesapeake, VA

Relax outdoors and watch the town come alive from the elevated vantage of holiday rentals with a balcony in Chesapeake, VA.

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 apartment, a short walk from the Commodore Theatre and the Virginia Sports Hall of Fame, enjoys a riverfront location offering scenic views and is within 2.4km of the Children's Museum of Virginia and the Portsmouth Naval Shipyard Museum.
The two-bedroom, one-bathroom flat sleeps four, features free WiFi, a DVD player, a fully equipped kitchen, on-site parking, and a terrace; board games and books are also provided for guests' entertainment.
Centrally Located Hampton Roads Home W/ Game Room! - Chesapeake, VA
No reviews

Centrally Located Hampton Roads Home W/ Game Room!

house, Portsmouth
This centrally located Hampton Roads detached house in Portsmouth offers easy access to attractions, situated 16 kilometres from Norfolk Botanical Garden and 35 kilometres from the King Neptune Statue on the Boardwalk.
This spacious 269 square metre property provides accommodation for up to 15 guests across four bedrooms, featuring a fully equipped kitchen, three bathrooms, air conditioning, a patio, a game room, and complimentary WiFi, with parking and a garden available.
Bright Chesapeake Home Near Shopping & Dining - Chesapeake, VA
9.2 11 reviews

Bright Chesapeake Home Near Shopping & Dining

house, Chesapeake
This two-bedroom house in Chesapeake, Virginia is conveniently located just 15 miles from Topgolf Virginia Beach and 19 miles from Mount Trashmore Park, offering easy access to both entertainment and nature. It has consistently received excellent ratings for user experience, location, and cleanliness, indicating a high standard of comfort and satisfaction for guests.
The 93 square metre property comfortably accommodates up to four guests and features a fully equipped kitchen, a private patio, and a spa. Guests can enjoy modern amenities such as free Wi-Fi, a cable flat-screen TV, and a washing machine, as well as a range of activities like golfing at the Virginia Beach National Golf Club and exploring the Virginia Living Museum.
Welcome To The Lighthouse!  Charming  3-bdrm Home With 2 Decks In Virginia Beach - Chesapeake, VA
8.0 3 reviews

Welcome To The Lighthouse! Charming 3-bdrm Home With 2 Decks In Virginia Beach

apartment, Virginia Beach
This Virginia Beach holiday home, a lighthouse property, is situated 1.6km from Regent University and a short drive from the interstate, providing easy access to beaches, the Virginia Beach Town Centre, and the Greenbrier Mall.
Sleeping six guests, this three-bedroom, three-bathroom property offers a kitchen with fridge, microwave, and dishwasher, air conditioning, a terrace, garden, parking, and Wi-Fi; nearby attractions include the Veterans United Home Loans Amphitheatre and Ocean Breeze Waterpark.

Best Chesapeake, VA holiday rentals with air conditioning

Southern Charm
Warm And Welcome - Chesapeake, VA
9.6 90 reviews

Southern Charm Warm And Welcome

apartment, Chesapeake
This Chesapeake apartment is located close to shopping and dining options, just a short distance from the interstate. It has received excellent ratings for its cleanliness, location, and overall user experience.
The apartment can comfortably accommodate up to four guests and features a fully equipped kitchen, a private garden with a fire pit and gas grill, and a washer and dryer for convenience. It also includes child-friendly amenities such as a highchair, pack and play, and a dedicated kiddie corner closet.
Stylish 3br Retreat Near Casino & Beach - Chesapeake, VA
9.8 20 reviews

Stylish 3br Retreat Near Casino & Beach

apartment, Portsmouth
This Portsmouth property, near Rivers Casino, offers a spacious three-bedroom house sleeping eight guests.
The self-catering house includes a kitchen, air conditioning, parking, and one bathroom, promising a relaxing stay close to Portsmouth's attractions and transport links, though precise distances require clarification.
Cute Space Near Towncenter 15 Minutes From Beaches - Chesapeake, VA
8.6 24 reviews

Cute Space Near Towncenter 15 Minutes From Beaches

apartment, Virginia Beach
This one-bedroom apartment is located in Northwest Virginia Beach, just 1.6 kilometres from the Sandler Center for the Performing Arts and Virginia Beach Town Center, and within 5 kilometres of Sentara Independence and Lynnhaven House. The apartment is situated in a peaceful residential area, offering a quiet retreat after a day of exploring the city. It has received very good user ratings, indicating a high level of satisfaction from previous guests.
The apartment features a comfortable living space with a sofa bed, accommodating up to 6 guests. It is equipped with amenities such as air conditioning, internet access, and a convenient location within walking distance of restaurants, shops, and entertainment options.
Cute Luxurious Home/va Beach! - Chesapeake, VA
10 2 reviews

Cute Luxurious Home/va Beach!

apartment, Virginia Beach
This newly renovated three-bedroom, two-and-a-half-bathroom house in Virginia Beach offers convenient access to Town Centre, various military bases, the airport, and beaches, all within a short driving distance (distances unspecified).
Sleeping seven guests, this self-catering property boasts a fully equipped kitchen, air conditioning, internet access, parking, and is perfect for families or groups seeking a longer stay, with a minimum 30-day rental period.

Top Rated Luxury Holiday Rentals in Chesapeake, VA

Treat yourself to smart-home features, high-end interiors, and curated artwork at luxury holiday rentals in Chesapeake, VA.

Spacious Retreat 3 Bed - Chesapeake, VA
No reviews

Spacious Retreat 3 Bed

house, Portsmouth

Top-Rated Downtown Holiday Rentals in Chesapeake, VA

Find centrally located holiday rentals in Chesapeake, VA close to attractions and transport.

The Refresh Experience - Chesapeake, VA
9.2 74 reviews

The Refresh Experience

house, Chesapeake
Fully Renovated And Modernized Home In Chesapeake - Chesapeake, VA
10 23 reviews

Fully Renovated And Modernized Home In Chesapeake

apartment, Chesapeake
Simply Amazing In Chesapeake - Chesapeake, VA
10 40 reviews

Simply Amazing In Chesapeake

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

The Full House

apartment, Chesapeake
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