Vacation Rentals in Chesapeake, VA

939 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Chesapeake, VA holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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.

3br, 6 Beds  Prime Stay Near Rivers Casino! - Chesapeake, VA
10 2 reviews

3br, 6 Beds Prime Stay Near Rivers Casino!

apartment, Portsmouth
This Portsmouth holiday home is situated within 5km of the Rivers Casino Portsmouth, the Commodore Theatre, and the Virginia Sports Hall of Fame, offering easy access to these attractions.
The three-bedroom property sleeps six guests and boasts a fully equipped kitchen with appliances including a dishwasher, a garden, parking, and free Wi-Fi, alongside a washing machine and barbecue facilities.
Coastal Comfort | Steps From Virginia Beach's Best - Chesapeake, VA
8.6 30 reviews

Coastal Comfort | Steps From Virginia Beach's Best

apartment, Virginia Beach
This Virginia Beach guesthouse, available for short-term lets from 1 February 2025, is situated in a residential area of Virginia Beach, its precise location and distance from the beach and boardwalk requiring further clarification.
Offering three bedrooms, one bathroom, and sleeping up to three guests, this fully furnished property includes a kitchen with fridge, freezer, microwave, and dishwasher, plus modern amenities such as central air conditioning, hardwood floors, and a washer/dryer; all utilities are included.
Lighthouse Launch - Spacious 4 Br/2ba Retreat - Chesapeake, VA
9.6 54 reviews

Lighthouse Launch - Spacious 4 Br/2ba Retreat

apartment, Portsmouth
This four-bedroom, two-bathroom house in a quiet Portsmouth neighbourhood is a short drive (approx. 5km) from Portsmouth's waterfront and around 48km from Virginia Beach.
This self-catering property sleeps eight, boasting a fully equipped kitchen, high-speed Wi-Fi, a Smart TV, and a washer/dryer, alongside exterior security cameras and a decibel monitor for a peaceful stay.
Waterfront Oasis: Fishing Pier, Pool, Beach Access - Chesapeake, VA
10 13 reviews

Waterfront Oasis: Fishing Pier, Pool, Beach Access

house, Chesapeake
This Chesapeake flat is located in the Deep Creek district, directly on the Elizabeth River, offering waterfront living with private marina club access, a fishing pier, docks, and beach access.
This 3-bedroom, 2-bathroom residence accommodates up to 8 guests and features air conditioning, internet, a kitchen, swimming pool, fitness centre, parking, and a dedicated dog park.

Best Chesapeake, VA holiday rentals with parking

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

Modern 1 Br Greenbrier Ches

apartment, Chesapeake
This one-bedroom flat is located in Summit Pointe, Chesapeake's urban district, placing you within easy reach of popular local attractions.
This stylish apartment accommodates two guests and offers amenities including air conditioning, internet, a kitchen, a swimming pool, a fitness centre, and parking.
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.
Located In A Quiet Northern Suffolk Neighborhood - Chesapeake, VA
9.7 23 reviews

Located In A Quiet Northern Suffolk Neighborhood

apartment, Suffolk
This Northern Suffolk flat is located in a peaceful area, offering easy access to Bennett Creek Park's amenities, including a boat ramp, and is a 15-minute drive from River Casino.
This updated rental accommodates six guests across three bedrooms and two bathrooms, featuring air conditioning and internet, and is situated within 3 kilometres of Bon Secours and Sentara Hospitals, with local dining options within 3.2 kilometres.
Jefferson Abbey Ii - Chesapeake, VA
9.1 105 reviews

Jefferson Abbey Ii

house, Chesapeake
This Chesapeake townhouse, ideally situated in Hampton Roads, offers easy access to I-64 and is within a short drive of Virginia Beach, approximately 20-30 km away depending on the specific beach.
The two-bedroom, two-bathroom property sleeps six guests comfortably, featuring two king-size master suites, a queen sleeper sofa, and modern amenities including a fully equipped kitchen, air conditioning, and free internet access; nearby attractions include Busch Gardens Williamsburg and the Portsmouth Casino.

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.

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.
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 Portsmouth waterfront apartment, situated near Bon Secours Maryview Hospital (within 8km), offers easy access to the city's naval bases and the Waterside District.
The one-bedroom flat sleeps two, includes a full kitchen with dishwasher, in-unit laundry, smart TVs, a terrace, and free off-street parking, plus nearby access to a tree swing and shared porch.
Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
10 1 review

Cheerful 2 Bedroom Home Near Virginia Wesleyan

apartment, Virginia Beach
This Northwest Virginia Beach holiday home is situated 0.5km from Virginia Wesleyan University, within 5km of Cypress Point Country Club, and less than 5km from Norfolk Premium Outlets.
This 89 square metre property offers two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen with oven and microwave, a private balcony, on-site barbecue grills, and in-unit laundry facilities.
Lovely Town Home - Chesapeake, VA
9.6 68 reviews

Lovely Town Home

apartment, Virginia Beach
This Virginia Beach house is located just 1.8 kilometres from Mount Trashmore Park, offering a peaceful escape from the city bustle, yet remaining within easy reach of the Virginia Beach Town Center and the Sandler Center for the Performing Arts. The property enjoys excellent guest ratings, highlighting its appeal for travellers.
This spacious home has four bedrooms and two bathrooms, comfortably accommodating up to ten guests. The house offers a range of amenities including a swimming pool, a jacuzzi, a garden, a terrace and parking, making it ideal for a relaxing and enjoyable stay.

Best Chesapeake, VA holiday rentals with air conditioning

Cozy Rambler - 3 Bd 2 Bath Home Full Of Charm - Chesapeake, VA
9.4 92 reviews

Cozy Rambler - 3 Bd 2 Bath Home Full Of Charm

apartment, Portsmouth
This apartment in Portsmouth is conveniently located just a short distance from the city centre, making it easy to explore its historic attractions and vibrant waterfront. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay for guests.
The apartment offers ample space for families or groups of up to six people, with two bathrooms for added convenience. Guests can enjoy a fully equipped kitchen, air conditioning, covered parking, and access to a private backyard, perfect for relaxing after a day of exploring the city.
The Mermaids Lair ‍️ - Chesapeake, VA
9.0 15 reviews

The Mermaids Lair ‍️

apartment, Portsmouth
This Portsmouth waterfront apartment offers stunning Crystal Lake views and private dock access, situated approximately 16km from Norfolk's attractions, 32km from Norfolk Naval Base, and 40km from Virginia Beach.
The self-catering studio, sleeping two guests, features a kitchenette with microwave and fridge, a custom shower, a shared fire pit, and automatic gate access for enhanced security.
Portsmouth 3br Near Casino, Comfy, Spacious Yard Stay, Sleeps 6! - Chesapeake, VA
9.2 19 reviews

Portsmouth 3br Near Casino, Comfy, Spacious Yard Stay, Sleeps 6!

apartment, Portsmouth
This Portsmouth holiday home is situated within 3km of the Commodore Theatre, Virginia Sports Hall of Fame and Museum, and Children's Museum of Virginia, and within 5km of the Portsmouth Naval Shipyard Museum.
The 130 square metre property boasts three bedrooms sleeping six, two bathrooms, a fully equipped kitchen, a jacuzzi, a terrace, a garden, parking, and free Wi-Fi; nearby attractions include the Tidewater Yacht Marina.
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.

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.

Cozy Chesapeake Retreat W/ Flex Room - Chesapeake, VA
No reviews

Cozy Chesapeake Retreat W/ Flex Room

apartment, Chesapeake

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

The Southern Magnolia | 2br/1bth Home

apartment, Chesapeake
Entire Apartment In Chesapeake, Virginia - Chesapeake, VA
9.8 12 reviews

Entire Apartment In Chesapeake, Virginia

apartment, Chesapeake
©2026 cozycozy.com