Holiday Rentals in Chesapeake, VA

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Chesapeake, VA holiday rentals
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677 Holiday Rentals and Airbnb in Chesapeake, VA

Best family friendly Chesapeake, VA holiday rentals

Among the 677 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals

Convenient Location! - Chesapeake, VA
10 52 reviews
Chesapeake, VA
01/07 – 31/07
NZ$383/nighttotal: NZ$11490 (30 )

Convenient Location!

1 2
apartment , Virginia Beach
This three-bedroom house in Virginia Beach is conveniently located 6km from Virginia Beach Town Centre and 21km from the beachfront, offering easy access to Norfolk via the Tide light rail, just 2km away.
Sleeping six guests, the property boasts a fully equipped kitchen with a Keurig coffee maker, a screened-in porch with gas grill, and three bedrooms featuring Zinnus mattresses; a king, a queen, and twin trundle beds, plus a newly renovated master bathroom.
2br Self Check-in, Fast Wi-fi - Chesapeake, VA
9.9 59 reviews
Chesapeake, VA
31/07 – 31/08
NZ$402/nighttotal: NZ$12462 (31 )

2br Self Check-in, Fast Wi-fi

1 2
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.
Sojourn At Colley Manor Unit 3 - Chesapeake, VA
10 1 review
Chesapeake, VA
31/07 – 31/08
NZ$250/nighttotal: NZ$7750 (31 )

Sojourn At Colley Manor Unit 3

2 2
apartment , Norfolk
This Ghent flat in Norfolk is situated near Colley Avenue, offering easy walking access to restaurants and cafes, and is a short drive (a few kilometres) from Virginia Beach and Ocean View.
The 81-square-metre (870 sq ft) self-catering property sleeps four, features two bedrooms, one bathroom, and includes amenities such as a dishwasher, air conditioning, parking, and Wi-Fi; a travel cot and high chair are available on request.
Convenient To All 7 Cities - Chesapeake, VA
9.2 52 reviews
Chesapeake, VA
17/07 – 20/07
NZ$715/nighttotal: NZ$2145 (3 )

Convenient To All 7 Cities

1 2
apartment , Chesapeake
This comfortable home in Chesapeake is conveniently located just a short distance from the Norfolk Waterside District, Rivers Casino, and Sentara/Obici Hospitals, making it a great base for exploring the area. It has received excellent ratings for location, cleanliness, and overall experience.
The house is spacious, with 176 square metres of living space and can accommodate up to six guests in its three bedrooms. It offers a fully equipped kitchen, a relaxing deck, and a private garden, perfect for enjoying a peaceful stay.

Best Chesapeake, VA holiday rentals with parking

Spacious 3 Bedroom Virginia Beach Getaway  30 + Night Stays - Chesapeake, VA
Chesapeake, VA
01/07 – 31/07
NZ$481/nighttotal: NZ$14430 (30 )

Spacious 3 Bedroom Virginia Beach Getaway 30 + Night Stays

3 2
apartment , Virginia Beach
This three-bedroom Virginia Beach apartment is situated in Northwest Virginia Beach, approximately 1.6km from Apex Entertainment, 3.2km from Cinema Cafe, and 4km from Mount Trashmore Park.
The 3-bedroom, 2-bathroom property sleeps six guests, boasting a fully equipped kitchen, high-speed Wi-Fi, Smart TV, in-unit laundry, and a fenced backyard; exterior security cameras and a decibel monitor ensure peace of mind.
Waterfront Portsmouth Apt: 1/2 Mi To Dtwn & Ferry - Chesapeake, VA
8.6 13 reviews
Chesapeake, VA
01/12 – 29/12
NZ$344/nighttotal: NZ$9632 (28 )

Waterfront Portsmouth Apt: 1/2 Mi To Dtwn & Ferry

2 2
apartment , Portsmouth
This Portsmouth apartment is situated near the Waterside District, less than 1.6km from Tidewater Yacht Marina and under 10 minutes’ drive from the Commodore Theatre and the Virginia Sports Hall of Fame.
The 116 square metre self-catering flat sleeps six, boasting three bedrooms, one bathroom, a fully equipped kitchen including a dishwasher, and on-site laundry facilities, plus an arcade for added entertainment.
Sojourn At Colley Manor Unit 2 - Chesapeake, VA
10 2 reviews
Chesapeake, VA
31/07 – 31/08
NZ$250/nighttotal: NZ$7750 (31 )

Sojourn At Colley Manor Unit 2

2 2
apartment , Norfolk
This Ghent flat in Norfolk is centrally located near Colley Avenue's restaurants and shops, within easy reach (by foot, bike, bus, or Tide light rail) of Norfolk city centre and major hospitals such as CHKD and Norfolk General Hospital, and a short drive (approximately 20-30 km) from Virginia Beach and Ocean View Beach.
This 93-square-metre (1000 sq ft) two-bedroom, one-bathroom apartment sleeps four, offering self-check-in, a fully equipped kitchen (including fridge, microwave, and dishwasher), air conditioning, parking, and internet access; pack 'n' play and high chair rentals are available for families.
Sojourn's Spacious Apartment In Colley Manor - Chesapeake, VA
9.6 4 reviews
Chesapeake, VA
12/10 – 18/02
NZ$250/nighttotal: NZ$32250 (129 )

Sojourn's Spacious Apartment In Colley Manor

2 2
apartment , Norfolk
This Ghent flat in Norfolk is situated near Colley Avenue's restaurants and cafes, major hospitals (CHKD, EVMS, and Norfolk General), and offers easy access to public transport, including the Tide light rail to Norfolk city centre.
The 84-square-metre (904-square-foot) two-bedroom, one-bathroom property sleeps four, includes a kitchen with a fridge, microwave, and dishwasher, and provides parking, air conditioning, internet access, and a contactless self check-in; a travel cot and high chair are available for an extra charge.

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.

Destinations nearby

Best Chesapeake, VA holiday rentals with a balcony

Charming 2 Br Vintage Duplex Upstairs Apartment In Historic Portsmouth Ac & Wifi - Chesapeake, VA
9.0 7 reviews
Chesapeake, VA
25/09 – 30/09
NZ$362/nighttotal: NZ$1810 (5 )

Charming 2 Br Vintage Duplex Upstairs Apartment In Historic Portsmouth Ac & Wifi

2 4
apartment , Portsmouth
This Portsmouth apartment is conveniently located near the Children's Museum of Virginia and the Portsmouth Naval Shipyard Museum, approximately 1.8 km away.
The two-bedroom, one-bathroom flat sleeps four guests and features a terrace, garden, fully equipped kitchen including oven, microwave and coffee maker, plus in-unit laundry facilities and free Wi-Fi.
Monthly, Dog-friendly Home At Orange Blossom - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
NZ$343/nighttotal: NZ$44247 (129 )

Monthly, Dog-friendly Home At Orange Blossom

3 2
apartment , Virginia Beach
This three-bedroom, four-bathroom apartment is situated in Virginia Beach's Green Run neighbourhood, approximately 24 kilometres from various beaches and close to Norfolk.
The self-catering property offers a spacious open-plan layout, sleeping up to five guests, and boasts a fully fenced backyard, on-site parking, and a fully equipped kitchen including a dishwasher; nearby attractions include Lynnhaven Mall, Landstown Commons, Town Centre, and Mount Trashmore Park.
Centrally Located Hampton Roads Home With Game Room! - Chesapeake, VA
Chesapeake, VA
25/09 – 30/09
NZ$685/nighttotal: NZ$3425 (5 )

Centrally Located Hampton Roads Home With Game Room!

4 2
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.
Fenced Yard And Patio! 2,400-sq-ft Chesapeake Home - Chesapeake, VA
10 1 review
Chesapeake, VA
25/09 – 30/09
NZ$1104/nighttotal: NZ$5520 (5 )

Fenced Yard And Patio! 2,400-sq-ft Chesapeake Home

4 2
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

Charming Pet‑friendly Retreat For Extended Stays - Chesapeake, VA
Chesapeake, VA
19/07 – 18/10
NZ$145/nighttotal: NZ$13195 (91 )

Charming Pet‑friendly Retreat For Extended Stays

1 1
apartment , Portsmouth
This Portsmouth apartment, near the Portsmouth/Norfolk border, is conveniently located 2.9km from the Children's Museum of Virginia and 6.1km from Rivers Casino Portsmouth.
The self-contained flat offers one bedroom, one bathroom, sleeps two guests, includes free parking, Wi-Fi, and a fully equipped kitchen with fridge, freezer, and microwave; small dogs and declawed cats are welcome.
Spacious Home In Chesapeake - Chesapeake, VA
9.5 2 reviews
Chesapeake, VA
08/07 – 13/07
NZ$1019/nighttotal: NZ$5095 (5 )

Spacious Home In Chesapeake

4 5
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.
Beachy And Chic 3 Bedroom Townhome Near Towncenter - Chesapeake, VA
10 3 reviews
Chesapeake, VA
29/06 – 03/08
NZ$442/nighttotal: NZ$15470 (35 )

Beachy And Chic 3 Bedroom Townhome Near Towncenter

1 2
apartment , Virginia Beach
This three-bedroom, two-bathroom townhouse is situated near Virginia Beach's Towne Centre, offering convenient access to Interstate 264, local military bases, and the Chesapeake Bay.
The property, sleeping up to seven guests, boasts a fully equipped kitchen, a downstairs workspace, and a large fenced backyard; nearby attractions include the Chesapeake Bay for water activities.
The Liberty Flat - Chesapeake, VA
10 24 reviews
Chesapeake, VA
25/09 – 30/09
NZ$254/nighttotal: NZ$1270 (5 )

The Liberty Flat

1 2
apartment , Portsmouth
This Olde Town Portsmouth flat, situated a short ferry journey from Norfolk and within walking distance of local restaurants, offers easy access to Virginia Beach, Norfolk, Williamsburg, and Yorktown.
The two-bedroom, one-bathroom apartment sleeps four, includes a kitchen with amenities for self-catering, and is anticipated to feature a washer/dryer; access is via stairs to the second floor.
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