Holiday Rentals in Chesapeake, VA

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Chesapeake, VA holiday rentals
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Best Holiday rentals and Airbnb offers 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

Portsmouth 3br Near Casino | Spacious Yard Stay - Chesapeake, VA
9.5 66 reviews

Portsmouth 3br Near Casino | Spacious Yard Stay

apartment, Portsmouth
This Portsmouth house is ideally situated just a short drive from the new Rivers Casino and within easy reach of downtown Portsmouth, Norfolk, Virginia Beach, and Chesapeake. The accommodation has received excellent ratings for cleanliness and location, and is rated very good overall.
The house has 3 bedrooms and 2 bathrooms, comfortably sleeping 6 guests. It features modern amenities like a kitchen with a fridge and microwave, a washer and dryer, high-speed Wi-Fi, multiple TVs with streaming services, a large fenced backyard with a patio, furniture, and a gas grill, and security features like exterior cameras and an ADT security system.
Executive Lakefront Oasis - Center Of Va. Beach - Chesapeake, VA
9.8 161 reviews

Executive Lakefront Oasis - Center Of Va. Beach

house, Virginia Beach
This lakefront property is located just 1.6 kilometres from the interstate and a short drive from both the beach and Virginia Beach Town Center, offering a convenient base for exploring the area. The house has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The spacious four-bedroom home spans 232 square metres and can comfortably accommodate up to 12 guests. Guests can enjoy a range of amenities, including a fully equipped kitchen, a private jacuzzi, a screened porch, and a garden with outdoor lighting, perfect for relaxing evenings.
Sojourn 2 Bedroom Townhouse In Virginia Beach - Chesapeake, VA
9.3 29 reviews

Sojourn 2 Bedroom Townhouse In Virginia Beach

apartment, Virginia Beach
This apartment is located just a few kilometres from the bustling heart of Virginia Beach, offering easy access to shops, restaurants and the beach. It has been rated very good for cleanliness and user experience, and excellent for location.
The apartment has two bedrooms and one bathroom, comfortably sleeping up to five guests. It comes equipped with a well-stocked kitchen, comfortable living space, and access to streaming services, ensuring a relaxing and enjoyable stay.
Simply Amazing In Chesapeake - Chesapeake, VA
10 40 reviews

Simply Amazing In Chesapeake

house, Chesapeake
This Chesapeake property is conveniently located just 5-10 kilometres from Greenbrier Mall, various shopping plazas, and restaurants, making it a great base for exploring the area. It also enjoys a prime position, being only 15 kilometres from the Virginia Beach oceanfront and 10 kilometres from Ocean View in Norfolk. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
This spacious home offers three bedrooms and two bathrooms, comfortably accommodating up to eight guests. The fully equipped kitchen features a fridge, freezer, microwave, and dishwasher, alongside a garden, parking, air conditioning, and internet access, ensuring a comfortable and enjoyable stay.

Best Chesapeake, VA holiday rentals with parking

Old World Charm - Chesapeake, VA
9.9 99 reviews

Old World Charm

apartment, Portsmouth
This charming flat is located in historic Olde Town Portsmouth, within easy walking distance of the city's top attractions like the Strawbery Banke Museum and Prescott Park. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The flat offers a spacious layout with a living room, kitchenette, two bathrooms, and a bedroom that can sleep two guests. Enjoy a comfortable stay with amenities such as air conditioning, a private garden, and on-site parking, all within a historic building that adds a unique touch to your Portsmouth experience.
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.
The Ponderosa A - Close To The Casino & Concerts - Chesapeake, VA
9.8 106 reviews

The Ponderosa A - Close To The Casino & Concerts

apartment, Portsmouth
This one-bedroom flat is located in a peaceful neighbourhood, just 800 metres from the Rivers Casino and a short drive from Portsmouth city centre (6.4km), Norfolk city centre (9.5km) and Virginia Beach (35.4km). It has received excellent ratings for its location, cleanliness, and overall user experience.
The flat has a private entrance and parking space, making it ideal for couples or solo travellers. It features a comfortable queen-size bed, a fully equipped kitchen with a fridge and microwave, air conditioning, a garden, and free Wi-Fi. Guests can enjoy easy access to nearby concerts, as well as day trips to other cities in the region.
Fully Renovated And Modernized Home In Chesapeake - Chesapeake, VA
10 23 reviews

Fully Renovated And Modernized Home In Chesapeake

apartment, Chesapeake
This Chesapeake apartment is conveniently located just 2 kilometres from Portlock Galleries at SoNo and an 8-minute drive from Greenbrier Mall. It has received excellent guest reviews, making it a popular choice for travellers. The apartment has 3 bedrooms and 3 bathrooms, comfortably accommodating up to 8 guests. The property comes with a range of features, including a Smart TV, Wi-Fi, parking, and a barbecue area, providing everything you need for a comfortable stay.

Frequently asked questions about holiday rentals in Chesapeake, VA

  • What are the top family-friendly attractions in Chesapeake, VA?

    The Chesapeake Arboretum is a great choice for families with its nature trails and gardens. The Children's Museum of Virginia is a fun place for kids of all ages, and the Chesapeake Bay Foundation's Brock Environmental Center offers educational and interactive exhibits about the bay.
  • 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.

  • 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 spring or autumn. The weather is mild and pleasant, and the crowds are smaller. You'll find good deals on rentals during these seasons.
  • What are the most popular Airbnbs in Chesapeake, VA?

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

    The Chesapeake Bay Wine Festival is a popular event in the area, held every year in the spring. The Chesapeake Arts Festival is another great choice, featuring live music, art exhibits, and food vendors. The Virginia Beach Boardwalk is a short drive from Chesapeake and hosts many events throughout the year.
  • What are the best vacation 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 vacation rentals with a pool in Chesapeake, VA.

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

    The Chesapeake Arboretum is a great option for a free day out, with its nature trails and gardens. The Chesapeake Bay Foundation's Brock Environmental Center also offers free admission. You can also enjoy a scenic walk or bike ride along the Chesapeake Bay.
  • 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 restaurants with local dishes in Chesapeake, VA?

    For local seafood, try The Fish House Restaurant in the Great Bridge area. They have a great view of the water and serve fresh, delicious dishes. For a more casual option, try The Chesapeake Inn, known for its crab cakes and other local favourites.
  • 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 best walking or cycling routes in Chesapeake, VA?

    The Chesapeake Bay Trail is a popular choice for walking or cycling, offering scenic views of the bay. The Dismal Swamp Canal Trail is another great option, with its historic significance and natural beauty.
  • Are there pet-friendly attractions in Chesapeake, VA?

    The Chesapeake Arboretum is very pet-friendly, allowing dogs on leashes. The Chesapeake Bay Foundation's Brock Environmental Center also welcomes well-behaved dogs on leashes.
  • What are the benefits of choosing a vacation rental in Chesapeake, VA?

    Vacation rentals offer more space and privacy than hotels. They are also often more affordable, especially for families or groups travelling together. Many vacation rentals offer unique features like kitchens, laundry facilities, and outdoor spaces.

Popular destinations

Best Chesapeake, VA holiday rentals with a balcony

Bright Chesapeake Home Near Shopping & Dining - Chesapeake, VA
9.2 11 reviews

Bright Chesapeake Home Near Shopping & Dining

house, Chesapeake
This two-bedroom house in Chesapeake, Virginia is conveniently located just 15 miles from Topgolf Virginia Beach and 19 miles from Mount Trashmore Park, offering easy access to both entertainment and nature. It has consistently received excellent ratings for user experience, location, and cleanliness, indicating a high standard of comfort and satisfaction for guests.
The 93 square metre property comfortably accommodates up to four guests and features a fully equipped kitchen, a private patio, and a spa. Guests can enjoy modern amenities such as free Wi-Fi, a cable flat-screen TV, and a washing machine, as well as a range of activities like golfing at the Virginia Beach National Golf Club and exploring the Virginia Living Museum.
Bright Chesapeake Home Near Shopping & Dining - Chesapeake, VA
No reviews

Bright Chesapeake Home Near Shopping & Dining

house, Chesapeake
House rental listing. You will stay in Chesapeake.
Services and facilities: free parking, air conditioning and a washing machine. This house also has a terrace!
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.
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.

Best Chesapeake, VA holiday rentals with air conditioning

Best Temporary Rental In Chesapeake - Chesapeake, VA
9.6 66 reviews

Best Temporary Rental In Chesapeake

house, Chesapeake
This two-bedroom townhouse is situated in the Greenbrier area of Chesapeake, just a short distance from shops, restaurants and the interstate. The property has consistently received excellent ratings for location, cleanliness and overall user experience.
The townhouse comfortably accommodates up to four guests and features a fully equipped kitchen with a fridge, microwave oven and dishwasher. Guests can enjoy a peaceful retreat in the garden, relax in the air-conditioned living space or explore the surrounding area with ease.
Private Boutique Apt W/d Near Casino & Downtown - Chesapeake, VA
9.8 27 reviews

Private Boutique Apt W/d Near Casino & Downtown

apartment, Portsmouth
This Westhaven flat is situated in Portsmouth, offering historic character and convenient access to Rivers Casino, NNSY, and Naval Station Norfolk, all within a few kilometres.
This two-bedroom residence accommodates up to four guests and includes a kitchenette, air conditioning, private parking, and an in-unit washer/dryer for a comfortable stay.
Cozy Modern Retreat, Peaceful Stay Near Everything - Chesapeake, VA
9.7 13 reviews

Cozy Modern Retreat, Peaceful Stay Near Everything

apartment, Portsmouth
This new-construction luxury flat in Portsmouth offers proximity to Historic Olde Towne Portsmouth and is a convenient 7-minute drive from the casino, placing it under 8 kilometres from Downtown Norfolk's premier dining and entertainment.
This spacious property accommodates up to 8 guests with 4 bedrooms and 3.5 bathrooms, featuring two master suites, a private backyard, a welcoming front porch, central air/heat, and high-speed WiFi.
Tiny House Spooky Themed Sept And Oct
Great Bridge - Chesapeake, VA
9.7 86 reviews

Tiny House Spooky Themed Sept And Oct Great Bridge

house, Chesapeake
This Chesapeake retreat offers direct access to a boat launch, numerous parks, and hiking trails, with scenic bike paths also within easy reach, placing you moments from the region's outdoor pursuits and dining options.
This one-bedroom, one-bathroom lodge accommodates two guests and features air conditioning, a kitchen, and internet, serving as an ideal base for exploring the natural beauty and amenities Chesapeake provides.
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