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.

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

Sojourn | Virginia Beach | 2 Bedroom Townhouse

apartment, Virginia Beach
This two-bedroom flat in Northwest Virginia Beach is situated opposite Virginia Wesleyan College, providing easy access to military bases such as Joint Base Little Creek (8 kilometres away), Norfolk Naval Station (16 kilometres away), and Master Jet Base Oceana (17.7 kilometres away), as well as Sentara Leigh Hospital (3.2 kilometres away).
This family-friendly residence accommodates up to five guests with a fully equipped kitchen, including a fridge, microwave, and dishwasher, air conditioning, Wi-Fi, smart TVs with Hulu Live and Netflix, and a garden, with parking available and a check-out time of 11:00 AM.
11 Mi To Virginia Beach Boardwalk: Studio Retreat! - Chesapeake, VA
9.7 48 reviews

11 Mi To Virginia Beach Boardwalk: Studio Retreat!

apartment, Virginia Beach
This Virginia Beach studio apartment is situated approximately 1.6 kilometres from Virginia Beach Town Centre, offering easy access to the beach and attractions such as the Virginia Aquarium & Marine Science Center and First Landing State Park.
The self-catering unit sleeps two guests and features a kitchenette with microwave and mini-fridge, a smart TV, free Wi-Fi, and access to a shared backyard; keyless entry is provided.
Sojourn At Colley Manor Steps From Local Favorites Unit #6 - Chesapeake, VA
No reviews

Sojourn At Colley Manor Steps From Local Favorites Unit #6

apartment, Norfolk
This Ghent, Norfolk flat is centrally located, within walking distance of Colley Avenue's cafes and restaurants, and a short drive (approximately 16km) from Virginia Beach and Ocean View.
The 93 square metre self-catering property offers two bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus air conditioning, parking, and internet access.
The Urbane Travel Experience - Chesapeake, VA
No reviews

The Urbane Travel Experience

apartment, Norfolk
This spacious Norfolk house, sleeping eight, is centrally located in a desirable neighbourhood; precise distances to Norfolk landmarks depend on the exact location within the city.
The 279-square-metre, three-storey property boasts four bedrooms, four bathrooms, a fully equipped kitchen with dishwasher, air conditioning, parking, and high-speed internet access.

Best Chesapeake, VA holiday rentals with parking

Condo Near Portsmouth Naval On Webster Avenue - Chesapeake, VA
10 30 reviews

Condo Near Portsmouth Naval On Webster Avenue

apartment, Portsmouth
This Portsmouth apartment, ideal for families or groups of up to six, is situated less than 1.6km from Portsmouth Naval Hospital and 8km from the Rivers Casino.
The three-bedroom, one-bathroom flat offers free internet, air conditioning, parking, and a fully equipped kitchen; enjoy easy access to local attractions and a peaceful atmosphere.
The Mermaids Lair ‍️ - Chesapeake, VA
9.2 151 reviews

The Mermaids Lair ‍️

apartment, Portsmouth
This charming guest house is situated just a short drive from Portsmouth, New Hampshire, offering easy access to the city's attractions while enjoying the peace and tranquility of Crystal Lake. The property has consistently received excellent ratings for its cleanliness, location, and overall guest experience.
The cosy house has one bedroom and one bathroom, comfortably accommodating up to two guests. Guests can enjoy stunning lake views, relax on the patio, or take advantage of the private dock and kayak access, as well as other amenities like a private fire pit and an automatic gate for added security.
Waterfront Oasis With Fenced Yard - Chesapeake, VA
9.7 309 reviews

Waterfront Oasis With Fenced Yard

house, Chesapeake
This charming townhouse is situated in Chesapeake, within easy reach of various landmarks, offering a peaceful lakefront setting with a tranquil atmosphere. It boasts excellent ratings for user experience, location, and cleanliness.
The property features an open-plan layout, perfect for families or groups of up to 8 guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and a laundry room on the second floor, ensuring a comfortable and convenient stay.
Spacious Retreat | Optional Guest House Add-on - Chesapeake, VA
9.2 15 reviews

Spacious Retreat | Optional Guest House Add-on

apartment, Portsmouth
This 3-bedroom flat in Portsmouth is located just minutes from the casino and Olde Towne Portsmouth's dining, shops, and nightlife.
This property accommodates up to six guests and features a fully stocked kitchen, a large backyard, and an entertainment-focused flex room with a 70-inch TV and game table, with Wi-Fi and smart TVs throughout.

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.
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 spacious four-bedroom flat in Portsmouth is situated conveniently for recreational parks and attractions, a mere 1.9 kilometres from the Norfolk Scope and Waterside District.
Offering 186 square metres of living space for up to eight guests, this residence features a private terrace, air conditioning, complimentary Wi-Fi, and a fully equipped kitchen, with on-site parking also provided.
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.
Bright Chesapeake Home Near Shopping & Dining - Chesapeake, VA
No reviews

Bright Chesapeake Home Near Shopping & Dining

house, Chesapeake
House listing. You will be located in Chesapeake.
Facilities and services: free parking, an iron and a washing machine. This house also has a terrace!

Best Chesapeake, VA holiday rentals with air conditioning

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 holiday home is located just 3km from attractions like the Emanuel AME Church, Commodore Theatre, and the Virginia Sports Hall of Fame and Museum, making it a great base for exploring the city. The surrounding area is quiet and residential, offering a peaceful escape from the hustle and bustle of the city centre.
The property has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It features a fully equipped kitchen, a terrace or balcony, a spa, and free parking, as well as modern amenities like Wi-Fi and air conditioning.
3 Bd Townhome Near Historic Waterfront Portsmouth - Chesapeake, VA
9.3 115 reviews

3 Bd Townhome Near Historic Waterfront Portsmouth

house, Portsmouth
This modern townhouse is ideally located in central Portsmouth, just a few kilometres from the Rivers Casino and the historic downtown district. It has received excellent ratings for location, cleanliness, and overall user experience.
The townhouse offers three bedrooms and one bathroom, comfortably accommodating up to six guests. It features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, as well as air conditioning, a garden, and parking.
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
This Chesapeake, Virginia aparthotel offers a convenient location, a 9-minute walk from the Chesapeake Conference Centre and a 1.8km drive from Greenbrier Mall, with easy beach access.
The self-catering apartment features a fully equipped kitchen, one bedroom, one bathroom, sleeps two guests, and includes a swimming pool, jacuzzi, and on-site parking.
The Mayfield - Chesapeake, VA
9.6 22 reviews

The Mayfield

apartment, Portsmouth
This Portsmouth apartment, perfect for families or solo travellers, offers two bedrooms, one bathroom, and sleeps five, boasting excellent user, location and cleanliness ratings.
The self-catering flat includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, and internet access.

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.

Nyakio Suite - Chesapeake - Chesapeake, VA
No reviews

Nyakio Suite - Chesapeake

apartment, Chesapeake

Top-Rated Downtown Holiday Rentals in Chesapeake, VA

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

The Full House - Chesapeake, VA
10 3 reviews

The Full House

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

Simply Amazing In Chesapeake

apartment, Chesapeake
The Refresh Experience - Chesapeake, VA
9.2 74 reviews

The Refresh Experience

house, Chesapeake
Entire Apartment In Chesapeake, Virginia - Chesapeake, VA
9.8 11 reviews

Entire Apartment In Chesapeake, Virginia

apartment, Chesapeake
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