Holiday Rentals in Chesapeake, VA

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

Best family friendly Chesapeake, VA holiday rentals

Among the 939 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals

3-bedroom Home Away From Home In Fabulous Chesapeake, Virginia. - Chesapeake, VA
10 54 reviews

3-bedroom Home Away From Home In Fabulous Chesapeake, Virginia.

apartment, Chesapeake
This three-bedroom Chesapeake house, located in the Great Bridge area, is 14 kilometres from Naval Station Norfolk and 39 kilometres from Virginia Beach's seafront.
The 148-square-metre property offers a king-size bed, a queen-size bed, and flexible twin beds (convertible to a king), accommodating up to six guests, and includes a full kitchen, washer/dryer, Wi-Fi, and a screened patio with a large fenced garden.
Sojourn's Spacious Apartment In Colley Manor - Chesapeake, VA
9.6 4 reviews

Sojourn's Spacious Apartment In Colley Manor

apartment, Norfolk
This Ghent flat in Norfolk is situated near Colley Avenue's restaurants and cafes, major hospitals (CHKD, EVMS, and Norfolk General), and offers easy access to public transport, including the Tide light rail to Norfolk city centre.
The 84-square-metre (904-square-foot) two-bedroom, one-bathroom property sleeps four, includes a kitchen with a fridge, microwave, and dishwasher, and provides parking, air conditioning, internet access, and a contactless self check-in; a travel cot and high chair are available for an extra charge.
Beautiful Home In Chesapeake - Chesapeake, VA
10 5 reviews

Beautiful Home In Chesapeake

house, Chesapeake
This Chesapeake property is conveniently located near Mount Trashmore Park (13km), the Norfolk Botanical Garden (20km), and Virginia Beach (a short drive away), offering easy access to local attractions and Norfolk International Airport (18km).
The 136 square metre house boasts three bedrooms, two bathrooms, sleeps twelve guests, and includes a fully equipped kitchen, free Wi-Fi, private parking, and air conditioning.
Kene's Luxury Retreat Near Va Beach+free Parking. - Chesapeake, VA
9.5 28 reviews

Kene's Luxury Retreat Near Va Beach+free Parking.

apartment, Portsmouth
This family-friendly, three-bedroom, two-storey residence is located in a residential area of Portsmouth, providing convenient access to local attractions such as the Historic Dockyard, approximately 3.5 kilometres away, without being in the immediate city centre.
This comfortable abode offers Wi-Fi, air conditioning, and parking, with a kitchen equipped with a freezer and dishwasher, accommodating up to eight guests and featuring a spacious backyard ideal for relaxation.

Best Chesapeake, VA holiday rentals with parking

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.
R & R River House - Chesapeake, VA
9.9 97 reviews

R & R River House

house, Portsmouth
This luxurious Portsmouth apartment boasts stunning water views and is conveniently located approximately 1.6km from a city park, 7.2km from a casino, and 11km from Portsmouth city centre.
The two-bedroom, one-bathroom property sleeps six guests and features a fully equipped kitchen with fridge, microwave, and dishwasher, air conditioning, a garden, parking, and a master bedroom with a private balcony; explore nearby attractions including Waterside, 12km away, and Virginia Beach, 40km away.
Rustic Downtown Living - 1br/1.5ba - Chesapeake, VA
9.9 33 reviews

Rustic Downtown Living - 1br/1.5ba

apartment, Norfolk
This apartment is located in the heart of Norfolk, just a short walk from the McArthur Center Mall and its cinema, offering easy access to the city's vibrant nightlife and attractions. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The one-bedroom flat comfortably accommodates two guests and features a modern, loft-style design with Brazilian hardwood floors and custom closets. Guests can enjoy amenities such as a fully equipped kitchen, high-speed internet, a separate laundry room, and parking, making it ideal for a comfortable and enjoyable stay in Norfolk.
Portsmouth Monthly Apt. (1717 D) - Chesapeake, VA
9.3 11 reviews

Portsmouth Monthly Apt. (1717 D)

apartment, Portsmouth
This Portsmouth apartment, situated less than 0.8km from the Interstate and the Downtown Tunnel to Norfolk, offers easy access to major roads and the city centre.
The two-bedroom, one-bathroom flat sleeps four guests and boasts a fully equipped kitchen, a 55-inch TV, high-speed Wi-Fi, ample on-site parking, and modern amenities, ideal for temporary workers or those seeking a comfortable Portsmouth stay.

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 or September to October, as the weather is still pleasant but the crowds are smaller. You'll find better deals on rentals during these months.
  • What are the best Airbnb and holiday rentals in Chesapeake, VA?

  • What events or festivals should visitors check out in and around Chesapeake, VA?

    Chesapeake has a few great events, like the Chesapeake Bay Wine Festival in the spring, and the Chesapeake Bay Seafood Festival in the fall. It's a great way to experience local culture and sample some delicious food and drink.
  • What are the most popular Airbnbs in Chesapeake, VA?

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

    Chesapeake has a lot to offer without breaking the bank. You can enjoy a free walk along the Chesapeake Bay Trail, or take a picnic to the Chesapeake Arboretum. There are also plenty of free concerts and events held throughout the year.
  • What are the best holiday rentals with a pool in Chesapeake, VA?

    Modern Condo In Western Branch, Comfortable Home | Long Stay Discount Available and The Peaceful Oasis are the best holiday rentals with a pool in Chesapeake, VA.

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

    If you're looking for a taste of Chesapeake, you should try the Chesapeake Bay Blue Crab at one of the local restaurants. The Crabby Shack and The Blue Crab are two popular options that serve up some delicious seafood.
  • 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 walking or cycling, it stretches for over 160 km and offers stunning views of the Chesapeake Bay. The Great Bridge Trail is another popular choice, it's a shorter trail, but it's perfect for a leisurely bike ride.
  • 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, there are a few pet-friendly attractions in Chesapeake. The Chesapeake Arboretum welcomes dogs on leash, and the Chesapeake Bay Trail is also dog-friendly. Many restaurants also have outdoor seating areas that are pet-friendly.
  • What are the benefits of choosing a vacation rental in Chesapeake, VA?

    Vacation rentals offer more space and privacy than a hotel room, and they are often more affordable, especially for families or groups. You'll also have access to a kitchen, which allows you to save money by preparing some of your own meals.
  • What are the top sports attractions and facilities in Chesapeake, VA?

    The Chesapeake Sports Complex is a popular destination for sports fans, it has several fields for baseball, softball, and soccer, as well as a track and field facility. The Chesapeake YMCA also offers a range of sports programs and facilities, including a swimming pool and fitness centre.

Popular destinations

Best Chesapeake, VA holiday rentals with a balcony

Bright Chesapeake Home Near Shopping & Dining - Chesapeake, VA
No reviews

Bright Chesapeake Home Near Shopping & Dining

house, Chesapeake
Holiday house to rent. You will be based in Chesapeake.
Services and facilities: a kitchen, a fridge and air conditioning. This house in Chesapeake also has a terrace!
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 house, near Topgolf Virginia Beach (8.7 km) and the Norfolk Botanical Garden (12 km), offers convenient access to local attractions.
The 186 square metre property boasts four bedrooms, three bathrooms, and sleeps up to 14 guests, featuring a fully equipped kitchen, free Wi-Fi, air conditioning, 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
This holiday home is located in Portsmouth, just 1.5 km from Rivers Casino Portsmouth, and within 10 km of Portsmouth City Park and Frank D Lawrence Stadium. It has consistently received excellent user ratings, making it a popular choice for travellers.
The property offers 93 square metres of space and can comfortably accommodate up to 6 guests in its 3 bedrooms. The kitchen comes equipped with a fridge, microwave, oven, and dishwasher, while the garden provides a relaxing outdoor space. Guests can also enjoy free Wi-Fi, air conditioning, a terrace, and parking.
Spacious Modern 3-bedroom House In Beautiful Portsmouth City. - Chesapeake, VA
8.0 1 review

Spacious Modern 3-bedroom House In Beautiful Portsmouth City.

apartment, Portsmouth
This four-bedroom, three-bathroom flat in Portsmouth is conveniently located 5.6 kilometres from Town Point Park and 16.1 kilometres from Chesapeake Bay, with the Children's Museum of Virginia and Portsmouth Naval Shipyard Museum a mere 2.4 kilometres away.
Guests can enjoy complimentary Wi-Fi, air conditioning, and on-site laundry facilities in this accommodation, which also features a sunroom or lanai and offers parking for up to six people.

Best Chesapeake, VA holiday rentals with air conditioning

Nyakio Suite - Chesapeake - Chesapeake, VA
No reviews

Nyakio Suite - Chesapeake

apartment, Chesapeake
This two-bedroom flat is located in Chesapeake's Greenbrier district, a 7-minute walk from Rivercrest Play Area and a 10-minute walk from Dominion Marketplace.
This 101 square metre residence accommodates up to four guests, featuring a fully equipped kitchen, air conditioning, Wi-Fi, a balcony, and access to an on-site swimming pool and parking.
The Calm Cottage | European Fireplace Retreat - Chesapeake, VA
10 8 reviews

The Calm Cottage | European Fireplace Retreat

apartment, Chesapeake
This countryside cottage near Chesapeake offers peaceful rural views and is within a 40-48 kilometre drive of Virginia Beach Oceanfront and Sandbridge Beach, with the Outer Banks (Nags Head) accessible within approximately 20 kilometres for a longer day trip.
This two-bathroom apartment accommodates up to five guests across three bedrooms, each featuring a television and massage recliner, and includes a fully equipped kitchen, a private deck, and an in-home washer and dryer for convenience.
Lakeside Living - Chesapeake, VA
9.4 17 reviews

Lakeside Living

apartment, Virginia Beach
This three-bedroom, two-bathroom lakeside property in Virginia Beach offers stunning lake and wildlife views, a private dock, and is conveniently located near major roads, shopping areas, and approximately 16 km from the city centre and airport.
The self-catering apartment sleeps five, boasts a large fenced garden with a firepit, a spacious sunroom with a gas fireplace, and welcomes small dogs (with prior approval and a fee); nearby activities include family-friendly attractions and Virginia Beach's nightlife.
Serene Tree House Retreat | Spacious 1br/1bth Home - Chesapeake, VA
9.9 32 reviews

Serene Tree House Retreat | Spacious 1br/1bth Home

apartment, Chesapeake
The Magnolia Tree House is situated in a peaceful residential neighbourhood in Chesapeake, just 15km south of downtown Norfolk, and within easy reach of attractions like Virginia Beach Town Center (27km) and the Virginia Beach Boardwalk (48km). This apartment has received excellent user ratings for cleanliness and location, and a very good rating overall.
The one-bedroom flat can comfortably accommodate two guests, and features a spacious and cosy layout. Amenities include a fully equipped kitchen, a private terrace with a fire pit and grilling area, a fitness centre, and parking.
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