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

Oasis At The Creek| Park, Family & Pet Friendly - Chesapeake, VA
9.8 67 reviews

Oasis At The Creek| Park, Family & Pet Friendly

apartment, Chesapeake
This three-bedroom house in Deep Creek, Chesapeake, is situated approximately 40km from the local airport and under 8km from restaurants and entertainment.
The self-catering property sleeps six, boasting a fully equipped kitchen with dishwasher, a garden, ample parking, TVs, washer/dryer, fireplace, gas grill, and a fully accessible backyard.
Elegance Escape On Saunders Dr - Chesapeake, VA
9.7 66 reviews

Elegance Escape On Saunders Dr

house, Portsmouth
This 3-bedroom holiday home is conveniently situated just a short walk from Portsmouth City Park and Elizabeth Manor Golf and Country Club, offering easy access to both relaxation and recreation.
The apartment comfortably sleeps 6 guests, with three bedrooms, a living room, and a dedicated entertainment area. Enjoy the spacious outdoor areas, including a patio, a front porch, a fire pit, and two grills, as well as a fully equipped kitchen and a swimming pool (open from May 25th to September 15th).
Cozy Ranch Home, Centrally Located Near Chicks Beach! - Chesapeake, VA
8.6 9 reviews

Cozy Ranch Home, Centrally Located Near Chicks Beach!

apartment, Virginia Beach
This Virginia Beach farmhouse, situated in the Northwest neighbourhood, is a 5-minute drive (approximately 3.2km) from Highway 264, offering easy access to the Virginia Beach Town Centre and other attractions.
Sleeping up to eight guests in three bedrooms and one bathroom, this self-catering property boasts a fully equipped kitchen, a relaxing backyard with a fire pit, and is conveniently located near the Veterans United Home Loans Amphitheatre and Ocean Breeze Waterpark.
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home - Chesapeake, VA
9.0 160 reviews

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

apartment, 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.

Best Chesapeake, VA holiday rentals with parking

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.
Remote-ready Apt With Workspace And Fenced Yard - Chesapeake, VA
10 7 reviews

Remote-ready Apt With Workspace And Fenced Yard

apartment, Portsmouth
This apartment offers a private retreat in Portsmouth, providing easy access to local amenities and attractions.
This modern, bright flat features a full kitchenette, a dedicated workspace with fast Wi-Fi, air conditioning, and a private, fenced garden with a patio, ideal for two guests with a complimentary off-street parking spot.
Historic Gem - Walk To Dining, Ferry & Waterfront - Chesapeake, VA
10 215 reviews

Historic Gem - Walk To Dining, Ferry & Waterfront

apartment, Portsmouth
This charming 1880s home is located in Olde Towne Portsmouth, just 1 kilometre from the Elizabeth River harbour, a 3-minute walk from the ferry to Norfolk's downtown and a 5-minute walk to High Street with its shops, restaurants, and cultural attractions. The property has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The house has three bedrooms and two bathrooms, accommodating up to seven guests. It offers a range of modern amenities, including a fully equipped kitchen, air conditioning, a private garden, parking, and free internet access, as well as unique historic features like original pinewood floors, windows, doors, and antique doorknobs.
Cute Luxurious Home/va Beach! - Chesapeake, VA
10 2 reviews

Cute Luxurious Home/va Beach!

apartment, Virginia Beach
This newly renovated three-bedroom, two-and-a-half-bathroom house in Virginia Beach offers convenient access to Town Centre, various military bases, the airport, and beaches, all within a short driving distance (distances unspecified).
Sleeping seven guests, this self-catering property boasts a fully equipped kitchen, air conditioning, internet access, parking, and is perfect for families or groups seeking a longer stay, with a minimum 30-day rental period.

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.
Centrally Located Hampton Roads Home W/ Game Room! - Chesapeake, VA
No reviews

Centrally Located Hampton Roads Home W/ Game Room!

house, Portsmouth
This centrally located Hampton Roads detached house in Portsmouth offers easy access to attractions, situated 16 kilometres from Norfolk Botanical Garden and 35 kilometres from the King Neptune Statue on the Boardwalk.
This spacious 269 square metre property provides accommodation for up to 15 guests across four bedrooms, featuring a fully equipped kitchen, three bathrooms, air conditioning, a patio, a game room, and complimentary WiFi, with parking and a garden available.
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.
Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
10 1 review

Cheerful 2 Bedroom Home Near Virginia Wesleyan

apartment, Virginia Beach
This Northwest Virginia Beach holiday home is situated 0.5km from Virginia Wesleyan University, within 5km of Cypress Point Country Club, and less than 5km from Norfolk Premium Outlets.
This 89 square metre property offers two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen with oven and microwave, a private balcony, on-site barbecue grills, and in-unit laundry facilities.

Best Chesapeake, VA holiday rentals with air conditioning

Near Casino, Va Beach, Large Yard,  Quite Relaxing - Chesapeake, VA
9.7 75 reviews

Near Casino, Va Beach, Large Yard, Quite Relaxing

house, Portsmouth
This Portsmouth apartment is conveniently located just 5.6 kilometres from the Norfolk Waterside District, 3.2 kilometres from Roger Browns and 5.6 kilometres from Rivers Casino, all while being situated in a peaceful neighbourhood. The apartment has received excellent ratings for location, cleanliness, and user experience.
The property features two separate suites, offering ample space for up to 7 guests. Amenities include a fully equipped kitchen, laundry facilities, a garden with patio furniture, a fitness centre and secure access with a keypad.
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.
Home With Historic Charm! Close To Naval Hospital! - Chesapeake, VA
9.6 5 reviews

Home With Historic Charm! Close To Naval Hospital!

apartment, Portsmouth
This Portsmouth apartment is situated in a quiet historic district, less than 1.6km from the Naval Medical Center Portsmouth and within 8km of several major Norfolk medical centres, including Sentara Norfolk General Hospital.
The three-bedroom, two-bathroom property sleeps five guests and boasts excellent amenities including air conditioning, parking, and internet access; nearby attractions include the Portsmouth waterfront and its restaurants.
Cozy Ranch Retreat. - Chesapeake, VA
9.4 35 reviews

Cozy Ranch Retreat.

house, Chesapeake
This stylish three-bedroom apartment is located in a central area, just a short drive from downtown Norfolk, Portsmouth Rivers Casino, and Virginia Beach, all within 30 kilometres. The property has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The apartment is spacious and welcoming, ideal for families or groups of up to six people. It includes a fully equipped kitchen, a comfortable living space, and a private garden, as well as access to a fitness centre and parking.
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