Best Holiday rentals and Airbnb offers in Chesapeake, VA
9.0 2 reviews
Chesapeake, VA
01/07 – 31/07
SG$212/nighttotal: SG$6360 (30 )
Sojourn At Colley Manor Unit 2 Sleeps 4
2 2
apartment , Norfolk
Colley Manor Unit 2, a two-bedroom apartment in Norfolk, is conveniently located 10.6 km from the Norfolk Botanical Garden and 14.3 km from Topgolf Virginia Beach. This 93 square metre self-catering property sleeps six guests comfortably and offers free Wi-Fi, a fully equipped kitchen with dishwasher, laundry facilities, cable TV, air conditioning, and parking.
9.8 78 reviews
Chesapeake, VA
25/09 – 30/09
SG$396/nighttotal: SG$1980 (5 )
Comfy House! The Perfect Getaway
1 4
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.
9.7 54 reviews
Chesapeake, VA
25/09 – 30/09
SG$313/nighttotal: SG$1565 (5 )
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.
10 5 reviews
Chesapeake, VA
16/08 – 27/08
SG$298/nighttotal: SG$3278 (11 )
Spacious, 2 Master Suites, Sleeps 6-8, 2.5 Baths
1 4
apartment , Chesapeake
This two-bedroom flat in Chesapeake offers a family-friendly stay with internet, air conditioning, and a well-equipped kitchen, featuring a fridge, freezer, microwave, and dishwasher. Sleeping up to eight guests, this accommodation boasts two master suites with en-suite bathrooms, flexible sleeping arrangements including king and queen beds, a queen air mattress, and an extendable dining table.
Chesapeake, VA
01/07 – 31/07
SG$212/nighttotal: SG$6360 (30 )
Sojourn At Colley Manor Unit 4 Sleeps 4
2 2
apartment , Norfolk
Colley Manor Unit 4, situated in Norfolk, is conveniently located 10.6 km from the Norfolk Botanical Garden and 14.3 km from Topgolf Virginia Beach, offering easy access to Virginia Beach attractions. This two-bedroom apartment, sleeping four, boasts a 93 square metre floor area, a fully equipped kitchen including a dishwasher, free Wi-Fi, and parking, making it ideal for families or small groups visiting Norfolk.
Chesapeake, VA
29/06 – 03/08
SG$289/nighttotal: SG$10115 (35 )
Large Home Perfect For Families & Traveling Crews
1 2
apartment , Chesapeake
This spacious flat is located in a residential district of Chesapeake, providing convenient access to local amenities and attractions. This four-bedroom flat accommodates up to eight guests and features a primary suite, a dedicated office, a well-equipped eat-in kitchen, a separate dining room, a garage with a washer and dryer, and a generous living room with a large sectional, all complemented by a large, fenced yard for outdoor enjoyment.
10 11 reviews
Chesapeake, VA
12/10 – 18/02
SG$210/nighttotal: SG$27090 (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
12/10 – 18/02
SG$121/nighttotal: SG$15609 (129 )
Steps To Elizabeth River & Dtwn! Portsmouth Condo
1 2
apartment , Portsmouth
This one-bedroom flat in Portsmouth is situated 8 minutes' walk from the Portsmouth Naval Shipyard Museum and 6 minutes' walk from the Commodore Theatre. This 56 square metre apartment accommodates two guests and features a fully equipped kitchen, air conditioning, on-site parking, and internet access, with a coin-operated laundry facility conveniently located nearby.
9.2 52 reviews
Chesapeake, VA
24/07 – 26/07
SG$589/nighttotal: SG$1178 (2 )
Convenient To All 7 Cities
1 4
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.
10 20 reviews
Chesapeake, VA
25/09 – 30/09
SG$257/nighttotal: SG$1285 (5 )
Condo Near Portsmouth Naval On Webster Avenue
1 4
apartment , Portsmouth
This Portsmouth apartment, ideal for families or groups of up to six, is situated less than 1.6km from Portsmouth Naval Hospital and 8km from the Rivers Casino. The three-bedroom, one-bathroom flat offers free internet, air conditioning, parking, and a fully equipped kitchen; enjoy easy access to local attractions and a peaceful atmosphere.
9.8 51 reviews
Chesapeake, VA
23/06 – 25/06
SG$219/nighttotal: SG$438 (2 )
Virginia Beach, Getaway
1 3
apartment , Virginia Beach
This modern one-bedroom apartment in Virginia Beach is situated on a quiet cul-de-sac, minutes from Lynnhaven Inlet, local shops, restaurants, and beaches, as well as the Virginia Beach Convention Center and sports facilities. The self-catering flat offers two queen-size beds sleeping up to four guests, a fully equipped kitchen, in-unit laundry, and a newly fitted bathroom; enjoy easy access to the area's attractions.
Chesapeake, VA
19/07 – 18/10
SG$232/nighttotal: SG$21112 (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.
Best family friendly Chesapeake, VA holiday rentals
Among the 677 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals
9.8 148 reviews
Chesapeake, VA
14/08 – 16/08
SG$1385/nighttotal: SG$2770 (2 )
Lakefront Oasis Centrally Located. Elegant, Spacious And You're Going To Love It
4 2
apartment , 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.
8.0 3 reviews
Chesapeake, VA
12/10 – 18/02
SG$169/nighttotal: SG$21801 (129 )
11 Mi To Virginia Beach Boardwalk: Studio Retreat!
1 2
studio , Virginia Beach
This Northwest Virginia Beach apartment is ideally situated 1.6km from the Virginia Beach Town Centre, offering easy access to shopping, dining, and the beach. The 33-square-metre self-catering studio sleeps two, features a kitchenette with microwave, mini-fridge and Keurig coffee maker, a shared backyard, and complimentary toiletries, plus driveway parking and a smart TV; nearby attractions include the Virginia Aquarium & Marine Science Center, First Landing State Park, and the Military Aviation Museum.
10 1 review
Chesapeake, VA
31/07 – 31/08
SG$355/nighttotal: SG$11005 (31 )
3br, 6 Beds Prime Stay Near Rivers Casino!
3 2
apartment , Portsmouth
This Portsmouth holiday home is situated within 5km of the Rivers Casino Portsmouth, the Commodore Theatre, and the Virginia Sports Hall of Fame, offering easy access to these attractions. The three-bedroom property sleeps six guests and boasts a fully equipped kitchen with appliances including a dishwasher, a garden, parking, and free Wi-Fi, alongside a washing machine and barbecue facilities.
10 1 review
Chesapeake, VA
31/07 – 31/08
SG$349/nighttotal: SG$10819 (31 )
Comfortable Retreat W/ Backyard & Parking
2 2
apartment , Portsmouth
This two-bedroom, one-bathroom duplex in Brighton, Portsmouth, is situated adjacent to the naval shipyard, offering a five-minute walk to the Portsmouth Naval Shipyard and a ten-minute drive to downtown Portsmouth's restaurants and entertainment. This family-friendly and pet-friendly flat provides accommodation for up to six guests, featuring a fully equipped kitchen with a fridge and microwave, air conditioning, on-site parking for one vehicle, and fast Wi-Fi, with self-check-in available via a smart lock.
Best Chesapeake, VA holiday rentals with parking
10 22 reviews
Chesapeake, VA
25/09 – 30/09
SG$340/nighttotal: SG$1700 (5 )
Escape To The Water!
1 4
apartment , Portsmouth
This Portsmouth holiday home, located near the waterfront, offers easy access to attractions such as Prescott Park and Strawbery Banke Museum, though the precise distance is unspecified. The two-bedroom, two-bathroom property sleeps six, features a fully equipped kitchen, air conditioning, parking, and internet access; guests can also enjoy lake access and two porches.
10 196 reviews
Chesapeake, VA
25/09 – 30/09
SG$344/nighttotal: SG$1720 (5 )
Gorgeous Olde Towne Historic Home - Modern Updates
3 4
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.
10 1 review
Chesapeake, VA
16/08 – 27/08
SG$344/nighttotal: SG$3784 (11 )
Cambridge Knights A 3 Bedroom Home Full Of Charm
3 4
apartment , Portsmouth
This Portsmouth holiday home is located just 3km from attractions like the Emanuel AME Church, Commodore Theatre, and the Virginia Sports Hall of Fame and Museum, making it a great base for exploring the city. The surrounding area is quiet and residential, offering a peaceful escape from the hustle and bustle of the city centre. The property has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It features a fully equipped kitchen, a terrace or balcony, a spa, and free parking, as well as modern amenities like Wi-Fi and air conditioning.
Chesapeake, VA
25/09 – 30/09
SG$323/nighttotal: SG$1615 (5 )
Walk To River & Downtown: Portsmouth Apartment!
2 4
house , Portsmouth
This Portsmouth apartment, located a short walk from the Riverfront and Portsmouth city centre, is approximately 14.5 kilometres from Norfolk Botanical Garden and 14 kilometres from Norfolk International Airport. This two-bedroom holiday home offers 111 square metres of space, sleeping up to seven guests and boasting free Wi-Fi, a fully equipped kitchen, and private parking.
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?
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?
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?
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?
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.
Destinations nearby
Best Chesapeake, VA holiday rentals with a balcony
9.0 7 reviews
Chesapeake, VA
25/09 – 30/09
SG$270/nighttotal: SG$1350 (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.
10 9 reviews
Chesapeake, VA
23/06 – 25/06
SG$588/nighttotal: SG$1176 (2 )
Bright Chesapeake Home Near Shopping & Dining
2 3
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.
9.5 2 reviews
Chesapeake, VA
25/09 – 30/09
SG$549/nighttotal: SG$2745 (5 )
Spacious Home In Chesapeake
4 4
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 1 review
Chesapeake, VA
25/09 – 30/09
SG$825/nighttotal: SG$4125 (5 )
Fenced Yard & Patio! 2,400-sq-ft Chesapeake Home
4 4
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
31/07 – 31/08
SG$172/nighttotal: SG$5332 (31 )
Dream Haven - 2br/2ba - Free Parking On Premises.
2 2
apartment , Chesapeake
This Chesapeake apartment rental, located in Western Branch North, offers easy access to Route 664, six minutes from local hospitals and a fifteen-minute drive from downtown Norfolk and its attractions, including the Waterside District and Norfolk Scope. The 111-square-metre (1194 square feet) property features two bedrooms, two bathrooms, sleeps four guests, and includes amenities such as a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, parking, internet access, and is close to Greenbrier Mall and Frank D Lawrence Stadium.
9.7 29 reviews
Chesapeake, VA
23/06 – 25/06
SG$510/nighttotal: SG$1020 (2 )
Bright Chesapeake Home Near Shopping & Dining
2 3
apartment , Chesapeake
This charming guest house is located in Chesapeake, just 42 kilometres from Virginia Beach, offering easy access to both the city and the nearby coastline. The property has consistently received excellent ratings for location, cleanliness, and overall user experience. The self-contained accommodation sleeps up to four guests and features a well-equipped kitchen, a private outdoor space, and modern amenities such as a Smart TV and free Wi-Fi. Guests can enjoy a covered porch, a private entrance, and the convenience of a washer and dryer.
9.4 78 reviews
Chesapeake, VA
25/09 – 30/09
SG$248/nighttotal: SG$1240 (5 )
Chesapeake. Comfy & Cozy. 4 Beds 2 Bath
1 4
apartment , Chesapeake
This three-bedroom apartment is situated in a peaceful area of Chesapeake, just 3km from Rivers Casino, 7km from Downtown Portsmouth, and 10km from Downtown Norfolk Waterside. The property has received excellent ratings for location, cleanliness, and user satisfaction. The apartment offers plenty of space for families or groups of friends, comfortably accommodating up to six guests. It features a well-equipped kitchen, air conditioning, a garden, parking, and internet access, as well as being pet-friendly.
Chesapeake, VA
29/06 – 03/08
SG$104/nighttotal: SG$3640 (35 )
Serene Retreat - Hot Tub, Private Dock & Fire Pit
1 2
apartment , Portsmouth
This private, fully furnished flat, with its own entrance, is located in a peaceful residential area of Portsmouth, offering waterfront views and direct access to a private dock. This accommodation comfortably sleeps two, features a separate bedroom, a living room with a convertible sofa, a breakfast bar, air conditioning, a hot tub, and parking, making it ideal for a relaxing stay.