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

Hidden Gem A Comfortable 4bedroom Home With A Fenced-in Yard. - Chesapeake, VA
10 10 reviews

Hidden Gem A Comfortable 4bedroom Home With A Fenced-in Yard.

apartment, Portsmouth
This Portsmouth holiday home is situated within 5km of Portsmouth City Park, Chesapeake Square Mall, and Rivers Casino Portsmouth, offering easy access to local amenities and attractions.
The 160 square metre property boasts four bedrooms, two bathrooms, sleeping up to eight guests, and features a fully equipped kitchen, garden, patio, free Wi-Fi, and parking.
Trycams Humble Abode - Chesapeake, VA
9.3 51 reviews

Trycams Humble Abode

apartment, Chesapeake
This Chesapeake property is conveniently located just a short drive from Virginia Beach, Busch Gardens, and the Virginia Aquarium, making it ideal for exploring the region's attractions. The accommodation has received excellent ratings for cleanliness and user experience, while its location has been rated very good.
This three-bedroom house can comfortably accommodate up to eight guests, with queen-sized beds in each bedroom and a queen-sized sofa bed downstairs. The house is well-equipped with a full kitchen, including a dishwasher, microwave, and other appliances, as well as a private outdoor space and parking.
11 Mi To Virginia Beach Boardwalk: Studio Retreat! - Chesapeake, VA
8.0 3 reviews

11 Mi To Virginia Beach Boardwalk: Studio Retreat!

studio, Virginia Beach
This Northwest Virginia Beach apartment is ideally situated 1.6km from the Virginia Beach Town Centre, offering easy access to shopping, dining, and the beach.
The 33-square-metre self-catering studio sleeps two, features a kitchenette with microwave, mini-fridge and Keurig coffee maker, a shared backyard, and complimentary toiletries, plus driveway parking and a smart TV; nearby attractions include the Virginia Aquarium & Marine Science Center, First Landing State Park, and the Military Aviation Museum.
2br Self Check-in, Fast Wi-fi - Chesapeake, VA
9.9 64 reviews

2br Self Check-in, Fast Wi-fi

apartment, Chesapeake
This apartment is conveniently located just a short drive from Virginia Beach, offering easy access to the beach, boardwalk, and various attractions. It has excellent user, location, and cleanliness ratings, making it a great choice for travellers.
The apartment comfortably sleeps four guests and features a spacious living area, two bedrooms, and a modern bathroom. It has a well-equipped kitchen with a fridge, freezer, microwave, dishwasher, and a washing machine and dryer, making it perfect for self-catering.

Best Chesapeake, VA holiday rentals with parking

Stylish 3br Retreat Near Casino & Beach - Chesapeake, VA
9.8 20 reviews

Stylish 3br Retreat Near Casino & Beach

apartment, Portsmouth
This Portsmouth property, near Rivers Casino, offers a spacious three-bedroom house sleeping eight guests.
The self-catering house includes a kitchen, air conditioning, parking, and one bathroom, promising a relaxing stay close to Portsmouth's attractions and transport links, though precise distances require clarification.
Cute Space Near Towncenter 15 Minutes From Beaches - Chesapeake, VA
8.6 27 reviews

Cute Space Near Towncenter 15 Minutes From Beaches

apartment, Virginia Beach
This one-bedroom apartment is located in Northwest Virginia Beach, just 1.6 kilometres from the Sandler Center for the Performing Arts and Virginia Beach Town Center, and within 5 kilometres of Sentara Independence and Lynnhaven House. The apartment is situated in a peaceful residential area, offering a quiet retreat after a day of exploring the city. It has received very good user ratings, indicating a high level of satisfaction from previous guests.
The apartment features a comfortable living space with a sofa bed, accommodating up to 6 guests. It is equipped with amenities such as air conditioning, internet access, and a convenient location within walking distance of restaurants, shops, and entertainment options.
Cozy Oasis - Close To Beaches, Downtown, Casino - Chesapeake, VA
9.0 160 reviews

Cozy Oasis - Close To Beaches, Downtown, Casino

house, Portsmouth
This Portsmouth apartment is located in a peaceful, historic neighbourhood, just a short distance from the city centre, the Elizabeth River and the beach. The property has been consistently rated excellent for location, cleanliness and overall experience.
The apartment is a spacious three-bedroom property that can comfortably accommodate up to seven guests. It offers a fully equipped kitchen, modern amenities such as high-speed Wi-Fi and a spa, as well as parking and a private entrance.
Nyakio Suite - Chesapeake, VA
No reviews

Nyakio Suite

apartment, Chesapeake
This Nyakio Suite flat is situated on the first floor in a quiet family district of Chesapeake, Virginia, offering a tranquil retreat.
This pet-friendly residence accommodates up to four guests, featuring two bedrooms, two bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, a decorative fireplace, and a private balcony overlooking a seasonal shared swimming pool, with internet and laundry facilities available.

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

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

Bright Chesapeake Home Near Shopping & Dining

house, Chesapeake
Vacation rental listing. You will be located in Chesapeake.
Services and facilities: a washing machine, a fridge and a kitchen. This house also has a terrace!
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.
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.

Best Chesapeake, VA holiday rentals with air conditioning

Newly Remodeled 2 Bedroom Duplex - Chesapeake, VA
10 3 reviews

Newly Remodeled 2 Bedroom Duplex

apartment, Chesapeake
This newly remodelled two-bedroom duplex apartment is situated in a peaceful Chesapeake neighbourhood, with the exact location and distances to landmarks unspecified.
The property, offering a king-size bed in the master and twin beds in the second bedroom, sleeps three guests and includes a fully equipped kitchen, in-unit laundry, Smart TVs, free Wi-Fi, and ample parking; this special offer includes a significant monthly discount.
15 Minutes To The Beach Bungalow - Chesapeake, VA
9.2 67 reviews

15 Minutes To The Beach Bungalow

apartment, Norfolk
This Norfolk holiday home, perfect for families, is situated in [Insert Precise Location, e.g., the village of Burnham Market, 10km from the Norfolk Coast and 20km from Sandringham House].
Sleeping eight guests across three bedrooms and two bathrooms, this self-catering property boasts a fully equipped kitchen, including a dishwasher, air conditioning, a garden, and ample parking.
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.
Sojourn | Virginia Beach | 2 Bedroom Townhouse - Chesapeake, VA
No reviews

Sojourn | Virginia Beach | 2 Bedroom Townhouse

apartment, Virginia Beach
This two-bedroom Virginia Beach apartment, ideal for families, offers convenient access to local shops and restaurants, its precise location undisclosed but within easy reach of Virginia Beach's attractions.
Sleeping five, the property boasts a fully equipped kitchen with dishwasher, a queen and full-size bed, Hulu Live and Netflix, plus parking and central air conditioning, with a pack 'n' play and high chair available for a fee (pre-booking essential).
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