Compare Vacation Rentals & Airbnb in Chesapeake, VA

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Chesapeake, VA vacation rentals
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939 Rentals and Airbnb in Chesapeake, VA

Best family friendly Chesapeake, VA vacation rentals

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

Prime Location In Chesapeake + Spacious 4br + Chef's Kitchen - Chesapeake, VA
9.4 9 reviews

Prime Location In Chesapeake + Spacious 4br + Chef's Kitchen

apartment, Chesapeake
This spacious four-bedroom flat in the Greenbrier district of Chesapeake is located approximately 40 kilometres from Virginia Beach, offering convenient access to Greenbrier Mall and Waterside District for shopping, as well as the Veterans United Home Loans Amphitheater for entertainment.
This family-friendly residence spans 186 square metres and accommodates up to eight guests, featuring a dedicated home theatre with a popcorn maker, a master suite with double vanities and a soaking tub, air conditioning, a garden, and parking.
3br Gem Near Rivers Casino  Comfort & Convenience - Chesapeake, VA
10 5 reviews

3br Gem Near Rivers Casino Comfort & Convenience

apartment, Portsmouth
This Portsmouth holiday home, ideally situated for exploring the city, offers easy access to Norfolk and Virginia Beach, and is conveniently located near the Waterside District and Greenbrier Mall shopping centres; distances to these attractions are not specified.
Sleeping six guests, this three-bedroom, one-bathroom apartment boasts a fully remodelled modern interior, including a fully equipped kitchen with dishwasher, in-unit laundry, air conditioning, a garden, parking, and Wi-Fi; five beds provide ample sleeping space.
Riverfront Portsmouth Home Near Casino & Patio - Chesapeake, VA
9.7 38 reviews

Riverfront Portsmouth Home Near Casino & Patio

apartment, Portsmouth
This Portsmouth waterfront house, located approximately 1.3 km from the Rivers Casino and 0.8 km from Historic Old Towne, offers stunning Elizabeth River views and private patio access.
Sleeping up to 10 guests, this three-bedroom, two-and-a-half-bathroom property boasts a fully equipped kitchen, high-speed Wi-Fi, and family-friendly amenities including a travel cot and high chair; nearby attractions include the Portsmouth Waterfront.
Walk To The Casino! Sleeps 8, Close To Everything - Chesapeake, VA
9.5 121 reviews

Walk To The Casino! Sleeps 8, Close To Everything

apartment, Portsmouth
This Portsmouth apartment is conveniently located within walking distance of the casino and a short drive (under 10km) to Norfolk, Virginia Beach, and Chesapeake. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes with a fully equipped kitchen, laundry facilities, a private backyard, and smart home features, ensuring a comfortable and enjoyable stay.

Best Chesapeake, VA vacation rentals with parking

Cozy Country Studio Apartment - Chesapeake, VA
9.5 38 reviews

Cozy Country Studio Apartment

house, Chesapeake
This Chesapeake studio apartment is peacefully located approximately 72km from Chesapeake's beaches, offering a tranquil retreat from city life.
The self-contained unit sleeps two guests, features a queen-size bed, well-equipped kitchenette, and private parking, perfect for exploring the Chesapeake area.
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 holiday home offers direct access to the 66km Seaboard Coastline Trail, providing easy exploration of the scenic coastal path.
The two-bedroom property sleeps six, boasting a fully renovated interior with a fireplace, complete kitchen, garden, parking, and bikes for guests to use, plus an outdoor fire pit.
Mid-century Modern Old Town Portsmouth 3bd/2.5 Bth - Chesapeake, VA
9.9 139 reviews

Mid-century Modern Old Town Portsmouth 3bd/2.5 Bth

apartment, Portsmouth
This charming house is located on a quiet street in Colonial Portsmouth, just a few hundred metres from the waterfront and next to a park. It has excellent user, location and cleanliness ratings, making it a great choice for a stay in Portsmouth.
The house has a spacious open-plan kitchen, dining and living area, perfect for families or groups of up to six people. The house is fully equipped with amenities including a kitchen, multiple bathrooms, a garden, parking and air conditioning, making it a comfortable and convenient place to stay.
Instant Serenity-just Add Water - Chesapeake, VA
No reviews

Instant Serenity-just Add Water

boat, Portsmouth
This Portsmouth waterfront vessel offers stunning sea views, situated approximately 16 kilometres from the Norfolk Botanical Garden and 14 kilometres from Norfolk International Airport.
The 43-square-metre boat features one bedroom, two bathrooms, and accommodates up to nine guests, boasting a fully equipped kitchenette with microwave and fridge, plus air conditioning, parking, and outdoor seating.

Frequently Asked Questions about vacation 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. You'll avoid the crowds and enjoy pleasant weather, with temperatures ranging from 15 to 25 degrees Celsius.
  • What are the best Airbnb and vacation rentals in Chesapeake, VA?

    King Guest Suite - A Togar Vacation Rental, Townhome In Convient Location and Econo Lodge Chesapeake Route 13 And I-464 are the most popular Airbnb and vacation rentals in Chesapeake, VA among travelers.

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

    Take a walk or bike ride along the Chesapeake Bay Trail, a scenic trail that stretches for over 160 km. You can also visit the Chesapeake Arboretum, a beautiful green space with free admission. And if you're looking for a fun and affordable way to spend an evening, check out the Chesapeake Farmers Market, held every Saturday from May to October.
  • What are the most popular Airbnbs in Chesapeake, VA?

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

    For a taste of Chesapeake's local seafood, try The Crab Pot, a popular spot known for its fresh blue crabs and other seafood dishes. Another great option is The Chesapeake Inn, a waterfront restaurant serving classic Chesapeake Bay dishes like crab cakes and oyster stew.
  • 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 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, offering scenic views of the Chesapeake Bay and its tributaries. You can also explore the Chesapeake Arboretum, which has a network of walking trails and a beautiful garden.
  • 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, there are plenty of pet-friendly attractions in Chesapeake. The Chesapeake Arboretum welcomes dogs on leash, and the Chesapeake Bay Foundation's Brock Environmental Center has a dog-friendly outdoor area. Many restaurants also have outdoor seating areas that are pet-friendly.
  • 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.

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

    Vacation rentals offer more space and privacy than hotels, and they often come with amenities like kitchens and laundry facilities. They can also be more affordable, especially for families or groups. Plus, you'll have the chance to experience life like a local, with access to neighbourhood amenities and a more authentic experience.
  • What are the top sports attractions and facilities in Chesapeake, VA?

    The Chesapeake Sportsplex is a popular destination for sports enthusiasts, with a variety of fields and courts for baseball, softball, soccer, and more. The Chesapeake YMCA also offers a range of sports activities and facilities, including a swimming pool, gym, and fitness classes.

Popular destinations

Best Chesapeake, VA vacation rentals with a balcony

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.
Fenced Yard & Patio! 2,400-sq-ft Chesapeake Home - Chesapeake, VA
10 1 review

Fenced Yard & Patio! 2,400-sq-ft Chesapeake Home

house, Chesapeake
This Chesapeake holiday home, situated 16km from Norfolk, offers easy access to attractions such as the Norfolk Botanical Garden (27km) and the King Neptune Statue (45km).
The 223 square metre property boasts four bedrooms, three bathrooms, sleeps fifteen guests, and includes a fully equipped kitchen, Wi-Fi, air conditioning, a garden, a spa, and on-site parking.
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.
Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
No reviews

Cheerful 2 Bedroom Home Near Virginia Wesleyan

apartment, Virginia Beach
This private two-bedroom townhome is located on a corner cul-de-sac lot in the Northwest district of Virginia Beach, offering a quiet setting just a short drive to First Landing State Park and the Virginia Aquarium.
This 89 square meter residence accommodates up to four guests, featuring a fully equipped kitchen with a wine cooler, a screened-in porch, an extra-large sectional sofa, and high-speed WiFi, with contactless entry for a seamless self-check-in experience.

Best Chesapeake, VA vacation 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.
Chesapeake Comfort - Chesapeake, VA
9.3 14 reviews

Chesapeake Comfort

apartment, Chesapeake
This Chesapeake flat is conveniently situated, offering a peaceful environment away from the city's hustle and bustle, ideal for both business travellers and families seeking a quiet stay.
This 3-bedroom, 2-bathroom abode accommodates up to 6 guests, featuring essential amenities such as air conditioning, parking, and a kitchen with a freezer and dishwasher, perfect for a comfortable and private visit.
The Mermaids Lair ‍️ - Chesapeake, VA
9.3 153 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.
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.
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