A golf course, a large building complex, and a marina by a river.

Holiday Homes in Chesapeake

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Chesapeake holiday homes

A covered porch with a hanging chair, a small table, and a view of a snowy yard.

1. 3-bedroom home away from home in fabulous Chesapeake, Virginia.

3-bedroom home away from home in fabulous Chesapeake, Virginia.
Chesapeake
10.0 out of 10, Exceptional, (54 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is NZ$536
includes taxes & fees
22 Sept - 23 Sept
3-bedroom home away from home in fabulous Chesapeake, Virginia.
A living room with a beige sofa, a white ottoman, a patterned rug, a wooden chair, and a small table.

2. Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Portsmouth
8.6 out of 10, Excellent, (11 reviews)
"It was perfect! Just what we needed for a quick visit with family and could bring the dog!"
United States
Kimberly
The price is NZ$378
includes taxes & fees
16 Sept - 17 Sept
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

3. Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Portsmouth
9.2 out of 10, Wonderful, (30 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
The price is NZ$546
includes taxes & fees
21 Sept - 22 Sept
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

4. Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.2 out of 10, Very good, (46 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
The price is NZ$586
includes taxes & fees
1 Oct - 2 Oct
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
A modern dining area with a glass table, blue upholstered chair, and black chairs.

5. Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (36 reviews)
"Great little house beach was good for small kids first trip to beach"
United States
Layton H.
The price is NZ$699
includes taxes & fees
24 Sept - 25 Sept
Sojourn | Coastal Cottage | 3 BR
A beach at sunset with a building in the background.

6. Cozy Beach Home in Oceanview

Cozy Beach Home in Oceanview
Bayview
9.8 out of 10, Exceptional, (47 reviews)
"Loved staying here. The house had everything that was needed and it was in close proximity to everything. "
United States
Conor L.
The price is NZ$615
includes taxes & fees
17 Sept - 18 Sept
Cozy Beach Home in Oceanview
A modern interior with a staircase, a door with a decorative glass panel, and a hallway with a tiled floor.

7. Bright 3-bedroom beach house with AC in charming Norfolk

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.4 out of 10, Exceptional, (9 reviews)
The price is NZ$664
includes taxes & fees
21 Sept - 22 Sept
Bright 3-bedroom beach house with AC in charming Norfolk
A narrow hallway with a white door, a bench, and a row of wooden stools.

8. Boho beach house w/foosball & patio

Boho beach house w/foosball & patio
Willoughby Spit
9.4 out of 10, Exceptional, (3 reviews)
"Extremely clean and family friendly. Easy access to the beach. Located in a quiet neighborhood"
United States
Mara
The price is NZ$819
includes taxes & fees
14 Sept - 15 Sept
Boho beach house w/foosball & patio
A modern kitchen with white cabinets, a wooden dining table, and a blue accent wall.

9. Beach Bungalow King Bed 1 Floor Living

Beach Bungalow King Bed 1 Floor Living
Bayview
9.6 out of 10, Exceptional, (23 reviews)
"The property was conveniently located at the beach yet close to Regent University. A great parents’ weekend and graduation getaway spot."
United States
Thomas M.
The price is NZ$811
includes taxes & fees
16 Sept - 17 Sept
Beach Bungalow King Bed 1 Floor Living
A compact room with a teal sofa, a white table, and a black chair.

10. Cozy 1-bedroom barn in amazing Hampton with cool AC

Cozy 1-bedroom barn in amazing Hampton with cool AC
Hampton
10.0 out of 10, Exceptional, (3 reviews)
"Great place and great value!"
United States
Jim K.
The price is NZ$270
includes taxes & fees
16 Sept - 17 Sept
Cozy 1-bedroom barn in amazing Hampton with cool AC
A sunlit room with a ceiling fan, two wicker chairs with cushions, a striped rug, and a small table with a plant.

11. Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ

Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
Cottage Park
9.0 out of 10, Wonderful, (6 reviews)
"Very nice place. We enjoyed the fire pit every night and the easy walk to the beach was a plus."
United States
Robin T.
The price is NZ$811
includes taxes & fees
15 Sept - 16 Sept
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
A modern kitchen with white cabinets, stainless steel appliances, and a large island with bar stools.

12. Charming 3bd - Near beaches - Foosball & Backyard

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.6 out of 10, Exceptional, (13 reviews)
"The property was great, 5 min walk to the beach. House was bright and cheery with plenty of space for our stay."
United States
Debbie M.
Charming 3bd - Near beaches - Foosball & Backyard
A kitchen with a wooden island, bar stools, a ceiling fan, and a refrigerator.

13. Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Bayview
8.6 out of 10, Excellent, (4 reviews)
The price is NZ$619
includes taxes & fees
30 Sept - 1 Oct
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
A spacious living room with a white sofa, a teal sectional, and a patterned rug.

14. Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard

Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard
Bayview
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful home that is very close to the ocean with lots of options of things to do. We had a wonderful stay!"
United States
Nate K.
The price is NZ$987
includes taxes & fees
21 Sept - 22 Sept
Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard
A residential driveway with a wooden fence, a concrete path, and a garage door.

15. Cozy 1-bedroom barn in marvelous Hampton with AC

Cozy 1-bedroom barn in marvelous Hampton with AC
Hampton
The price is NZ$342
includes taxes & fees
19 Sept - 20 Sept
Cozy 1-bedroom barn in marvelous Hampton with AC

16. Beautiful, spacious home in welcoming Norfolk.

Beautiful, spacious home in welcoming Norfolk.
Norfolk
7.4 out of 10, Good, (3 reviews)
"Host was great, very responsive. The house was great and very clean. Very quiet neighborhood. Short drive to everything Norfolk and Virginia Beach had to offer."
United States
shereece t.
The price is NZ$1,090
includes taxes & fees
7 Oct - 8 Oct
Beautiful, spacious home in welcoming Norfolk.
A beach with a wooden boardwalk, sand dunes, and the ocean in the background.

17. 3 bedroom home by the Sea, a block from the beach!

3 bedroom home by the Sea, a block from the beach!
Bayview
10.0 out of 10, Exceptional, (1 review)
"Fantastic home and host! Neighboring also came out welcome us and offer info about the area! Comfy bed and sofa too! Beach was super close!"
United States
Becky G.
3 bedroom home by the Sea, a block from the beach!
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

18. Wooded Wonderland

Wooded Wonderland
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"Great property not too far from the beaches! Between the pool, hot tub, mini golf, and theater room, our family had plenty to do at the house when we weren't out exploring Virginia Beach. Owner was quick to respond to any questions or needs as well."
United States
Erin W.
The price is NZ$1,128
includes taxes & fees
14 Sept - 15 Sept
Wooded Wonderland
A waterfront view from a wooden deck with a white railing, a dock extending into the water, and a clear blue sky.

19. Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Willoughby Spit
7.4 out of 10, Good, (3 reviews)
"Great house"
United States
sarah a.
The price is NZ$804
includes taxes & fees
14 Sept - 15 Sept
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!

20. Hot Tub | 9 beds | Fenced Yard

Hot Tub | 9 beds | Fenced Yard
Downtown Hampton
4.8 out of 10, (8 reviews)
"Convenient location and plenty of space, but the house is in clear disrepair. We were in town to see our daughter graduate from Hampton University, and the location was ideal for the ceremony."
United States
Kristin J.
The price is NZ$940
includes taxes & fees
14 Sept - 15 Sept
Hot Tub | 9 beds | Fenced Yard
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Hotel Reviews

Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront

8/10 Good
"Location is amazing. The restaurant staff was not friendly at all."
Amanda 2-night trip
Posted 7 hours ago
Hilton Virginia Beach Oceanfront

Find out more about Chesapeake

Chesapeake Holiday Homes information

Number of reviews
320
Accommodation
1312 Holiday Homes
Lowest Price
NZ$270
Highest Price
NZ$1,128