Compare Vacation Rentals & Airbnb in Chesapeake, VA

939 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Chesapeake, VA vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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

Extended Stay 3br 
With Gated Yard. - Chesapeake, VA
10 8 reviews

Extended Stay 3br With Gated Yard.

apartment, Norfolk
This Norfolk apartment is conveniently located just a few kilometres from the city centre, with easy access to attractions like the zoo, outlets and beaches, making it an ideal base for exploring the area. It boasts excellent ratings for location, cleanliness and user experience, ensuring a comfortable and enjoyable stay.
The apartment has three bedrooms and one bathroom, accommodating up to four guests. It features a well-equipped kitchen, a private patio, a dedicated workspace, laundry facilities and a welcome breakfast basket, providing everything you need for a relaxing and comfortable stay.
Country Escape Home In The Woods- Chesapeake, Va - Chesapeake, VA
10 25 reviews

Country Escape Home In The Woods- Chesapeake, Va

apartment, Chesapeake
This apartment is situated in a peaceful rural area of Chesapeake, Virginia, just 2.4 kilometres from Ballahack Airsoft Field and other attractions. It has received excellent user ratings, making it a popular choice for travellers.
The apartment offers 121 square metres of space, comfortably accommodating up to six guests in its three bedrooms and one bathroom. Guests can enjoy a range of amenities, including a fully equipped kitchen, a garden, a spa, parking, and access to the internet.
Sunny Dayz - Chesapeake, VA
9.2 52 reviews

Sunny Dayz

apartment, Chesapeake
This comfortable home in Chesapeake is conveniently located just a short distance from the Norfolk Waterside District, Rivers Casino, and Sentara/Obici Hospitals, making it a great base for exploring the area. It has received excellent ratings for location, cleanliness, and overall experience.
The house is spacious, with 176 square metres of living space and can accommodate up to six guests in its three bedrooms. It offers a fully equipped kitchen, a relaxing deck, and a private garden, perfect for enjoying a peaceful stay.
Private 1 Bed Apt - Historic Olde Towne Portsmouth - Chesapeake, VA
10 7 reviews

Private 1 Bed Apt - Historic Olde Towne Portsmouth

apartment, Portsmouth
This Portsmouth city centre flat is located a short walk from restaurants, museums, the historic Theatre, and the ferry terminal providing access to Norfolk’s Waterside District and MacArthur Mall, and is within 13km of a new casino.
The one-bedroom, one-bathroom apartment sleeps two guests and offers a fully equipped kitchen including a fridge, microwave, dishwasher, air fryer, and cast iron skillet, plus air conditioning and internet access; street parking is available.

Best Chesapeake, VA vacation rentals with parking

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

Bright Chesapeake Home Near Shopping & Dining

house, Chesapeake
Vacation house. You will be based in Chesapeake.
Facilities and services: a fridge, an iron and a kitchen. Take advantage of the air conditioning in this house!
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.
The Manor- Extended Stays - Chesapeake, VA
10 5 reviews

The Manor- Extended Stays

apartment, Chesapeake
This Chesapeake apartment, near Greenbrier Mall, offers easy access to the Oceanfront, Norfolk Waterside, and Norfolk Outlets.
The four-bedroom, two-bathroom property sleeps eight, features a recently remodelled kitchen with modern appliances, a 65-inch TV, free Wi-Fi, and self check-in; nearby attractions include the Chesapeake Jubilee and Deep Creek Locks.
Modern Portsmouth Apartment: Walk To Norfolk Ferry - Chesapeake, VA
9.5 20 reviews

Modern Portsmouth Apartment: Walk To Norfolk Ferry

apartment, Portsmouth
This Portsmouth apartment, situated on the Elizabeth River, offers easy access to Olde Towne Portsmouth and the Norfolk ferry, placing you within easy reach of historical sites and attractions.
The 120 square metre, single-storey flat sleeps six, boasting a fully equipped kitchen, in-unit laundry, a Smart TV, and free street parking, with a second apartment available in the same building for larger groups.

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

Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood. - Chesapeake, VA
No reviews

Historical Section Of Chesapeake. Propertie Nice And Groomed Quiet Neighborhood.

apartment, Chesapeake
This one-bedroom flat is located in Chesapeake, just a short distance from Norfolk's waterfront and a 32-kilometre drive from Virginia Beach's oceanfront. The surrounding area is quiet and offers easy access to local restaurants, supermarkets, and the city centre.
The flat is spacious and comfortably accommodates up to four guests. It comes with free curbside parking, air conditioning, internet access, and a relaxing front porch.
Spacious Modern 3-bedroom House In Beautiful Portsmouth City. - Chesapeake, VA
No reviews

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.
Boutique Private 2nd Floor 2br Apartment  W/d  Near Casino & Downtown - Chesapeake, VA
No reviews

Boutique Private 2nd Floor 2br Apartment W/d Near Casino & Downtown

apartment, Portsmouth
This private upstairs flat in historic Westhaven, Portsmouth, is conveniently located 4 kilometres from Rivers Casino, 2 kilometres from Portsmouth City Park, and offers proximity to the Commodore Theatre and Portsmouth Naval Shipyard Museum.
This two-bedroom apartment accommodates up to four guests, featuring a kitchenette, a full-size washer and dryer, air conditioning, internet, and private off-street parking for one vehicle.
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.

Best Chesapeake, VA vacation rentals with air conditioning

The Mermaids Lair ‍️ - Chesapeake, VA
9.0 14 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.
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.
5-bedroom Home In Chesapeake W/ Pool & Gym. Close To Shopping And Restaurants! - Chesapeake, VA
8.0 2 reviews

5-bedroom Home In Chesapeake W/ Pool & Gym. Close To Shopping And Restaurants!

apartment, Chesapeake
This four-bedroom apartment in Chesapeake provides convenient access to attractions such as Cinemark Chesapeake Square, located 2.8 kilometres away, and Portsmouth City Park, 3.1 kilometres distant.
This property accommodates up to 10 guests with four bedrooms, three bathrooms, and versatile sleeping arrangements including three queen beds and a twin bed, alongside air conditioning, Wi-Fi, and a swimming pool.
The Lodge! 1br Studio With Private Entrance. - Chesapeake, VA
9.8 85 reviews

The Lodge! 1br Studio With Private Entrance.

studio, Virginia Beach
This Virginia Beach studio apartment boasts a central location, approximately 24km from the Virginia Beach Boardwalk and 24km from the city centre.
The self-catering unit sleeps two, features a kitchenette with a cooktop, free on-site parking, and is equipped with linens, towels, and cookware.
©2026 cozycozy.com