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

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.
Shipside Suite~fast Wi-fi, Backyard Oasis, Family - Chesapeake, VA
9.0 2 reviews

Shipside Suite~fast Wi-fi, Backyard Oasis, Family

apartment, Portsmouth
This Portsmouth flat is situated 3 minutes' walk from the Children's Museum of Virginia and the Portsmouth Naval Shipyard Museum, offering convenient access to local attractions.
This 88 square metre residence accommodates up to six guests, featuring two bedrooms, one bathroom, air conditioning, Wi-Fi, and a garden with a fire pit and barbecue.
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.
Waterfront Oasis With Fenced Yard - Chesapeake, VA
9.7 311 reviews

Waterfront Oasis With Fenced Yard

house, Chesapeake
This charming townhouse is situated in Chesapeake, within easy reach of various landmarks, offering a peaceful lakefront setting with a tranquil atmosphere. It boasts excellent ratings for user experience, location, and cleanliness.
The property features an open-plan layout, perfect for families or groups of up to 8 guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, and a laundry room on the second floor, ensuring a comfortable and convenient stay.

Best Chesapeake, VA holiday rentals with parking

Beautiful, Modern Furnished 3-bedroom, 2-bathroom Cottage Near Attractions. - Chesapeake, VA
10 13 reviews

Beautiful, Modern Furnished 3-bedroom, 2-bathroom Cottage Near Attractions.

apartment, Portsmouth
This Portsmouth cottage, situated 3.5km from Bon Secours Maryview Medical Center and 7.6km from Portsmouth Naval Hospital, offers easy access to major roads, shopping centres, and restaurants.
The 111 square metre property comprises three bedrooms, two bathrooms, sleeps six guests, and includes a fully equipped kitchen with appliances such as an Instant Pot and air fryer, plus on-site parking and in-unit laundry facilities.
Comfy 1-bedroom Guesthouse With Free Parking. - Chesapeake, VA
10 43 reviews

Comfy 1-bedroom Guesthouse With Free Parking.

house, Norfolk
This guesthouse is conveniently located in downtown Norfolk, just a short drive from both Virginia Beach (40km) and historic Williamsburg (50km). The surrounding area is peaceful and offers easy access to restaurants and attractions. Guests have consistently rated the guesthouse as excellent for cleanliness, location, and overall experience.
The property features one bedroom and one bathroom, comfortably accommodating up to two guests. It offers modern amenities such as air conditioning, parking, a fully equipped kitchen with a fridge and microwave, and internet access. Guests can also enjoy scenic views and access to bike and walking trails.
Luxury Lakefront Estate & Guest House W/ Pool - Chesapeake, VA
10 10 reviews

Luxury Lakefront Estate & Guest House W/ Pool

house, Portsmouth
This luxurious lakefront estate sits on Crystal Lake, offering a tranquil retreat just 10km outside of Portsmouth, providing easy access to the city's attractions. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a top choice for discerning travellers.
The estate features a grand main house and a separate guest house, accommodating up to 16 guests. Guests can enjoy a refreshing dip in the pool, relax in the Jacuzzi, or prepare meals in the gourmet kitchen, all while taking in stunning lake views.
Luxurious 3 Bedrooms Townhouse Newly Renovated - Chesapeake, VA
9.5 139 reviews

Luxurious 3 Bedrooms Townhouse Newly Renovated

house, Virginia Beach
This newly remodelled Virginia Beach condominium, offering self-check-in, is situated in an unspecified location within the city, requiring further details regarding proximity to specific attractions.
The 1225 sq ft (113.7 sq m) property boasts three bedrooms, two bathrooms, and sleeps six, featuring a modern kitchen with granite countertops, stainless steel appliances, and two TVs.

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.
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.
Welcome To The Lighthouse!  Charming  3-bdrm Home With 2 Decks In Virginia Beach - Chesapeake, VA
8.0 3 reviews

Welcome To The Lighthouse! Charming 3-bdrm Home With 2 Decks In Virginia Beach

apartment, Virginia Beach
This Virginia Beach holiday home, a lighthouse property, is situated 1.6km from Regent University and a short drive from the interstate, providing easy access to beaches, the Virginia Beach Town Centre, and the Greenbrier Mall.
Sleeping six guests, this three-bedroom, three-bathroom property offers a kitchen with fridge, microwave, and dishwasher, air conditioning, a terrace, garden, parking, and Wi-Fi; nearby attractions include the Veterans United Home Loans Amphitheatre and Ocean Breeze Waterpark.
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.

Best Chesapeake, VA holiday rentals with air conditioning

Modern Comfort Minutes From Waterside & Downtown - Chesapeake, VA
9.5 30 reviews

Modern Comfort Minutes From Waterside & Downtown

apartment, Norfolk
This three-bedroom, two-bathroom flat is situated in a quiet Norfolk neighbourhood, just 1.6 kilometres from Downtown Norfolk, the Waterside District, and Norfolk State University.
This accommodation offers parking, air conditioning, and a fully equipped kitchen, with a guest capacity of five people and a back porch for relaxation.
3 Bedroom Home, King's Forest Va. Beach, Virginia - Chesapeake, VA
9.7 131 reviews

3 Bedroom Home, King's Forest Va. Beach, Virginia

house, Virginia Beach
This Virginia Beach home, a licensed Homeshare property, is ideally situated 9.6km from Virginia Beach's oceanfront and 3.2km from Town Centre, adjacent to a park featuring tennis courts, a playground, and a fishing pond.
Sleeping six guests across three bedrooms and one bathroom, this recently refurbished house offers a private driveway, private washer/dryer, a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, and parking, with the owner residing separately on the property.
Downtown Corner Of W. Bute & Dunmore Streets - Chesapeake, VA
9.5 146 reviews

Downtown Corner Of W. Bute & Dunmore Streets

apartment, Norfolk
This one-bedroom flat is situated in a historic neighbourhood in Norfolk, just a few hundred metres from cobblestone streets, gourmet restaurants and the YMCA, and within easy walking distance of the Chrysler Museum of Art. It has received excellent ratings for its location, cleanliness and overall user experience.
The flat can accommodate up to four guests and offers a range of amenities including a well-equipped kitchen, air conditioning, parking, and internet access. Guests can enjoy the outdoor space with benches on three sides of the building, perfect for relaxing or people-watching, and the flat also welcomes small, well-behaved pets.
Harbor Haven Retreat - Chesapeake, VA
9.6 18 reviews

Harbor Haven Retreat

apartment, Portsmouth
This spacious Portsmouth, Virginia house is centrally located in the historic downtown area, within walking distance of shops and restaurants, and a short drive (distances unspecified) from local beaches and the Portsmouth Casino.
Sleeping up to 15 guests in five bedrooms and three bathrooms, this fully equipped property boasts a kitchen with fridge, microwave, dishwasher and washer/dryer, air conditioning, a garden, parking, and excellent guest reviews.
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