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

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chesapeake holiday homes

Terrace/patio

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, (49 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is £228
includes taxes & fees
25 Aug - 26 Aug
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Interior

2. Prime Location in Chesapeake + Spacious 4BR + Chef's Kitchen

Prime Location in Chesapeake + Spacious 4BR + Chef's Kitchen
Chesapeake
9.2 out of 10, Wonderful, (7 reviews)
"Large rooms, good location, overall a nice place to stay with a larger group"
United States
Courtney K.
The price is £610
includes taxes & fees
15 Aug - 16 Aug
Prime Location in Chesapeake + Spacious 4BR + Chef's Kitchen
Dining

3. Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (9 reviews)
"Quiet comfortable"
United States
Rebecca K
The price is £209
includes taxes & fees
31 Aug - 1 Sept
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Coffee/tea maker, fridge, microwave, oven

4. 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, (29 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 £225
includes taxes & fees
8 Sept - 9 Sept
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Smart TV, fireplace

5. 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 £175
includes taxes & fees
8 Sept - 9 Sept
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Coffee/tea maker, fridge, microwave, oven

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

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.2 out of 10, Very good, (44 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
The price is £257
includes taxes & fees
1 Sept - 2 Sept
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Beach nearby, sun-loungers, beach towels

7. 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 £248
includes taxes & fees
8 Sept - 9 Sept
Cozy Beach Home in Oceanview
Games room

8. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very nice! And the host was in full contact with us throughout our stay to make sure we had everything we needed. Also, our family LOVED the video games. "
United States
Elaine P.
The price is £460
includes taxes & fees
1 Sept - 2 Sept
Centrally Located Hampton Roads Home w/ Game Room!
Dining

9. 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 £317
includes taxes & fees
8 Sept - 9 Sept
Sojourn | Coastal Cottage | 3 BR
Smart TV

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

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Bayview
9.0 out of 10, Wonderful, (2 reviews)
"Enjoyed walking to the beach."
United States
Donna G.
The price is £265
includes taxes & fees
8 Sept - 9 Sept
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Coffee/tea maker, fridge, microwave, oven

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

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.6 out of 10, Exceptional, (11 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.
The price is £316
includes taxes & fees
24 Aug - 25 Aug
Charming 3bd - Near beaches - Foosball & Backyard
Dining

12. Wooded Wonderland

Wooded Wonderland
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"Little too cold for swimming but the pool was beautiful. House was very clean and comfortable. We had 8 staying and we didn’t feel on top of each other. One of our party left her jewelry behind but the owner was great and arrangements where made to get them back to her. Would definitely stay again!"
United States
Dawn J.
The price is £523
includes taxes & fees
7 Sept - 8 Sept
Wooded Wonderland
Living area

13. Beautiful, spacious home in welcoming Norfolk.

Beautiful, spacious home in welcoming Norfolk.
Norfolk
2.0 out of 10, (1 review)
"We got to the property and it was double booked. This was after I communicated with the property manager. "
United States
Stephanie F.
The price is £459
includes taxes & fees
17 Aug - 18 Aug
Beautiful, spacious home in welcoming Norfolk.
Interior

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

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
8.8 out of 10, Excellent, (5 reviews)
The price is £333
includes taxes & fees
20 Aug - 21 Aug
Bright 3-bedroom beach house with AC in charming Norfolk
Private kitchen

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

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Willoughby Spit
The price is £373
includes taxes & fees
20 Aug - 21 Aug
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Smart TV, video games, ping pong, books

16. 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, (20 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 £472
includes taxes & fees
17 Aug - 18 Aug
Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard
Interior

17. Large 2 bedroom | Queen beds | Safe Area

Large 2 bedroom | Queen beds | Safe Area
Wythe
7.8 out of 10, Good, (10 reviews)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is £258
includes taxes & fees
8 Sept - 9 Sept
Large 2 bedroom | Queen beds | Safe Area
Beach

18. 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.
The price is £376
includes taxes & fees
11 Sept - 12 Sept
3 bedroom home by the Sea, a block from the beach!
Smart TV, fireplace, books, stereo

19. Unique Luxurious Waterfront in Hampton

Unique Luxurious Waterfront in Hampton
Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Great value for the money, great hosts, very renter friendly"
United States
WILLIAM M.
The price is £411
includes taxes & fees
18 Aug - 19 Aug
Unique Luxurious Waterfront in Hampton
Smart TV

20. Beachside Bliss Block from the Shore - Seahorse

Beachside Bliss Block from the Shore - Seahorse
East Ocean View
10.0 out of 10, Exceptional, (1 review)
Beachside Bliss Block from the Shore - Seahorse
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

Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

8/10 Good
"Wasc cleaning, restaurant/bar was very good but slow/understaffed at times, like breakfast. Decent gym, small indoor pool no hot tub. Could hear much more than i wanted in the hall and via the room connecting doors. Overall, id stay there again."
Greg 5-night trip
Posted 2 hours ago
Crowne Plaza Virginia Beach Town Center by IHG

Find out more about Chesapeake

Chesapeake Holiday Homes information

Number of reviews
251
Accommodation
1349 Holiday Homes
Lowest Price
£175
Highest Price
£610