This three-bedroom, two-bathroom flat in Norfolk's Berkley district is situated just 160 metres from Sentara Hospital and the Norfolk Naval Shipyard, with the Elizabeth River also nearby. This well-appointed apartment accommodates up to six guests and features modern décor, a fully equipped kitchen with high-quality cookware, comfortable sleeping arrangements, high-speed Wi-Fi, smart TVs, and a basement game room with a pool table.
Chesapeake, VA
12/10 – 18/02
NZ$332/nighttotal: NZ$42828 (129 )
Central Chesapeake Stay Near Mall, Trails & Parks
3 2
apartment , Chesapeake
This three-bedroom flat in Chesapeake is situated in the Greenbrier district, offering convenient access to Greenbrier Mall, Waterside District, and the Veterans United Home Loans Amphitheater at Virginia Beach, with major highways readily available for exploring the wider Hampton Roads area. This accommodation accommodates up to eight guests and provides air conditioning and internet, making it a comfortable base for exploring local attractions such as Jillian's Billiards and the Chesapeake Arboretum.
Chesapeake, VA
01/07 – 31/07
NZ$284/nighttotal: NZ$8520 (30 )
Sojourn At Colley Manor Unit 6 Sleeps 4
2 2
apartment , Norfolk
Colley Manor Unit 6, a two-bedroom apartment in Norfolk, is conveniently located approximately 10.6 km from the Norfolk Botanical Garden, 19.3 km from Mount Trashmore Park, and 14.3 km from Topgolf Virginia Beach. This 93 square metre self-catering flat sleeps six guests comfortably and offers free Wi-Fi, a fully equipped kitchen with dishwasher, in-unit laundry facilities, cable TV, and parking.
9.8 34 reviews
Chesapeake, VA
14/08 – 16/08
NZ$411/nighttotal: NZ$822 (2 )
The Harlequin Cottage
1 2
house , Suffolk
This charming cottage is situated in Suffolk, Virginia, just a short distance from the Decoys Seafood Restaurant and Bennett's Creek Marina, offering a peaceful retreat with easy access to local attractions. The cottage features a private entrance, luxurious ensuite bathroom with double sinks and walk-in showers, plush towels, and a king-size bed with soft linens. The cottage is perfect for a couple seeking a romantic getaway, with a small kitchen bar equipped with a mini fridge, microwave, Keurig, and complimentary coffee. Enjoy stunning views of historical Bennett's Creek, with the potential to see dolphins and otters, and take advantage of the resort-style amenities, including a seasonal 14,000 square foot tiki bar with a shared saltwater pool, swim-up bar, outdoor kitchen, and live music.
8.7 43 reviews
Chesapeake, VA
08/07 – 13/07
NZ$371/nighttotal: NZ$1855 (5 )
Cancun Daze
1 5
house , Chesapeake
This centrally located Chesapeake house offers easy access to various attractions and amenities within the city. The three-bedroom, two-bathroom property sleeps eight guests, boasting a king-size master bedroom, two queen bedrooms, a queen pull-out sofa in the loft, and modern amenities including fast Wi-Fi, TVs with streaming capabilities, and a fully equipped kitchen.
10 11 reviews
Chesapeake, VA
12/10 – 18/02
NZ$281/nighttotal: NZ$36249 (129 )
Modern Portsmouth Apartment: Walk To Norfolk Ferry
2 2
apartment , Portsmouth
This Portsmouth apartment, located near the Waterside District, is less than 1.6km from Tidewater Yacht Marina and within a 10-minute drive of the Commodore Theatre and Virginia Sports Hall of Fame. The 116 square metre property offers three bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen with dishwasher, in-unit laundry, free Wi-Fi, parking, and a sofa bed.
Chesapeake, VA
19/07 – 18/10
NZ$122/nighttotal: NZ$11102 (91 )
Riverbend Retreat - 1 Bedroom
1 1
apartment , Chesapeake
This private in-law suite offers direct access to the Elizabeth River, situated on a 1.5-hectare property in a tranquil area of Chesapeake. This one-bedroom flat provides complimentary kayak access for exploring the waterways, free parking, and a fully equipped kitchen, ideal for extended stays of 90 nights or more.
8.6 37 reviews
Chesapeake, VA
01/12 – 29/12
NZ$103/nighttotal: NZ$2884 (28 )
Park View Place - Apt 1 - Historic Olde Towne
1 2
apartment , Portsmouth
This charming apartment is located in Olde Towne Portsmouth, a historic district just next to Red Lion Park, offering a peaceful retreat within walking distance of the city's attractions. The property enjoys excellent ratings for location, cleanliness, and overall user experience. The apartment can accommodate up to 3 guests and features a comfortable living space with modern amenities like a smart TV, high-speed Wi-Fi, and a well-equipped kitchen. Guests can enjoy the convenience of air conditioning, parking, and access to a shared common space, making this a perfect choice for families or groups seeking a comfortable and convenient stay in Portsmouth.
9.7 55 reviews
Chesapeake, VA
16/08 – 27/08
NZ$324/nighttotal: NZ$3564 (11 )
Best Temporary Rental In Chesapeake
1 4
house , Chesapeake
This two-bedroom townhouse is situated in the Greenbrier area of Chesapeake, just a short distance from shops, restaurants and the interstate. The property has consistently received excellent ratings for location, cleanliness and overall user experience. The townhouse comfortably accommodates up to four guests and features a fully equipped kitchen with a fridge, microwave oven and dishwasher. Guests can enjoy a peaceful retreat in the garden, relax in the air-conditioned living space or explore the surrounding area with ease.
Chesapeake, VA
19/07 – 18/10
NZ$311/nighttotal: NZ$28301 (91 )
Walk To River & Downtown: Portsmouth Apartment!
2 1
apartment , Portsmouth
This Portsmouth apartment, near the Children's Museum of Virginia (a 0.9km walk) and the Portsmouth Naval Shipyard Museum (a 1.1km walk), offers convenient access to local attractions. The 111-square-metre property comprises three bedrooms, one bathroom, and on-site parking, plus in-unit amenities including a washer/dryer, full kitchen, and air conditioning; BBQ facilities are also available.
10 1 review
Chesapeake, VA
31/07 – 03/08
NZ$251/nighttotal: NZ$753 (3 )
Central 1 Bedroom Cute Apartment
1 2
apartment , Norfolk
This centrally located Norfolk city centre flat offers easy access to MacArthur Centre shopping mall, Norfolk Scope Arena, and the Norfolk Botanical Garden, all within a few kilometres. The one-bedroom apartment sleeps two guests, features a queen-sized bed, a fully equipped kitchen, air conditioning, parking, and includes complimentary toiletries; nearby attractions include diverse dining and entertainment options.
9.8 30 reviews
Chesapeake, VA
16/08 – 27/08
NZ$387/nighttotal: NZ$4257 (11 )
Cowbell Cottage
1 4
apartment , Chesapeake
Cowbell Cottage, a three-bedroom Chesapeake countryside retreat, is situated a short drive from Chesapeake city centre, offering easy access to local amenities. This self-catering property sleeps eight guests and boasts a kitchen, air conditioning, internet access, and pet-friendly accommodation.
Best family friendly Chesapeake, VA holiday rentals
Among the 677 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals
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.
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.
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.
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
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.
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.
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.
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?
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?
Best Chesapeake, VA holiday rentals with a balcony
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.
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.
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.
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
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.
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.
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.
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.