Holiday Rentals in Chesapeake, VA

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Chesapeake, VA holiday rentals
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939 Holiday Rentals and Airbnb 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

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.
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.
Cozy Modern Cabin - Chesapeake, VA
9.4 182 reviews

Cozy Modern Cabin

apartment, Portsmouth
This brick cabin is located just 6km from Portsmouth city centre, offering a peaceful retreat near the Elizabeth River. The property consistently receives excellent ratings for its cleanliness, location, and overall experience.
The cabin has four bedrooms and a well-equipped kitchen, perfect for families or groups. Guests can enjoy a range of amenities including a garden, parking, and air conditioning, as well as features like a large TV, a dishwasher, and free laundry soap.
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.

Best Chesapeake, VA holiday rentals with parking

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.
Stylish Two Bdrm, 1 1/2 Bth, King Bed Townhouse - Chesapeake, VA
9.9 63 reviews

Stylish Two Bdrm, 1 1/2 Bth, King Bed Townhouse

apartment, Portsmouth
This two-bedroom apartment in Portsmouth is situated less than a mile from the new Rivers Casino, offering easy access to entertainment and dining options. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The property can comfortably accommodate up to four guests and features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher. The apartment also benefits from air conditioning, a garden, and parking, ensuring a comfortable and convenient stay.
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.
Fully Renovated And Modernized Home In Chesapeake - Chesapeake, VA
10 25 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

  • 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 find fewer crowds and more affordable rates during these months. The weather is still pleasant, and you can enjoy all the attractions without the summer rush.
  • What are the best Airbnb and holiday rentals in Chesapeake, VA?

  • What are the best walking or cycling routes in Chesapeake, VA?

    The Chesapeake Bay Trail is a popular walking and cycling route that stretches along the Chesapeake Bay waterfront. The Great Bridge Battlefield and Waterways History Trail is another good option, offering a scenic route through the historic Great Bridge area. For a shorter walk, try the Chesapeake Arboretum's nature trails.
  • What are the most popular Airbnbs in Chesapeake, VA?

  • Are there pet-friendly attractions in Chesapeake, VA?

    The Chesapeake Arboretum is pet-friendly, and you can bring your furry friend along for a walk on the trails. The Chesapeake Bay Maritime Museum also welcomes well-behaved dogs on a leash.
  • What are the best holiday 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 holiday rentals with a pool in Chesapeake, VA.

  • What are the top sports attractions and facilities in Chesapeake, VA?

    The Chesapeake Regional Healthcare YMCA offers a variety of fitness classes, swimming pools, and sports courts. The Chesapeake City Park has tennis courts, baseball fields, and a playground. For golf enthusiasts, the Chesapeake Golf Club offers a challenging 18-hole course.
  • 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 rentals or Airbnbs with a jacuzzi in Chesapeake, VA?

    The best holiday 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.

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.
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.
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.
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.

Best Chesapeake, VA holiday rentals with air conditioning

Old Towne Charm - Chesapeake, VA
9.4 75 reviews

Old Towne Charm

apartment, Portsmouth
This Portsmouth apartment, situated in a historic neighbourhood a 1.6km walk from local pubs and the Naval Medical Center Portsmouth, offers easy access to Norfolk (16km away).
The second-floor, three-bedroom, two-bathroom flat sleeps six, features a fully equipped kitchen (including fridge and microwave), air conditioning, parking, a fitness centre, and excellent guest reviews; nearby attractions include Portsmouth Historic District.
The Cozy Calm | Indoor Fireplace | Luminest Homes - Chesapeake, VA
No reviews

The Cozy Calm | Indoor Fireplace | Luminest Homes

apartment, Virginia Beach
This Virginia Beach flat is conveniently located a 3-minute drive (approximately 500 meters) from Indian Lakes Crossing for shopping and dining, a 5-minute drive (approximately 800 meters) from Stumpy Lake Natural Area for outdoor pursuits, and a 7-minute drive (approximately 1.1 kilometres) from Regent University.
This 2-bedroom, 2-bathroom flat accommodates up to 4 guests and features air conditioning, Wi-Fi, a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, and an indoor fireplace, making it ideal for extended stays.
Comfy House! The Perfect Getaway - Chesapeake, VA
9.8 91 reviews

Comfy House! The Perfect Getaway

apartment, Chesapeake
This Chesapeake house, location unspecified, offers a three-bedroom, two-bathroom dwelling ideal for families or groups of up to six.
The property features a fully equipped kitchen, air conditioning, parking, and internet access, promising a comfortable stay.
Waterfront Maryview/naval Hosp Casino Close To All - Chesapeake, VA
9.6 292 reviews

Waterfront Maryview/naval Hosp Casino Close To All

apartment, Portsmouth
This apartment is situated on the Elizabeth River in a peaceful, upscale neighbourhood of Portsmouth, offering easy access to the city's attractions and the waterfront. It has received excellent ratings for its cleanliness, location, and overall experience.
The apartment has three bedrooms and one bathroom, accommodating up to eight guests. It features a modern kitchen with granite countertops and stainless steel appliances, a spacious living area, and a private mother-in-law suite with its own entrance, along with a large garden, parking, and Wi-Fi access.
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