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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

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 AU$479
includes taxes & fees
1 Sept - 2 Sept
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Coffee/tea maker, fridge, microwave, oven

2. 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 AU$459
includes taxes & fees
24 Aug - 25 Aug
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Smart TV, fireplace

3. 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
8.4 out of 10, Very good, (9 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 AU$332
includes taxes & fees
1 Sept - 2 Sept
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Games room

4. 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 AU$871
includes taxes & fees
1 Sept - 2 Sept
Centrally Located Hampton Roads Home w/ Game Room!
Beach nearby, sun-loungers, beach towels

5. 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 AU$555
includes taxes & fees
4 Aug - 5 Aug
Cozy Beach Home in Oceanview
Smart TV

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

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Bayview
10.0 out of 10, Exceptional, (1 review)
"Very Clean, beautiful property situated just blocks from the beach. Neighborhood was very friendly. The entire stay in this charming cottage was delightful!"
United States
Todd C.
The price is AU$520
includes taxes & fees
1 Sept - 2 Sept
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Coffee/tea maker, fridge, microwave, oven

7. Three blocks from the beach 2

Three blocks from the beach 2
Buckroe Beach
9.8 out of 10, Exceptional, (38 reviews)
"Nice clean place in a good location."
United States
Everett P.
The price is AU$477
includes taxes & fees
9 Aug - 10 Aug
Three blocks from the beach 2
Dining

8. Cozy Ranch Home, Centrally Located near Chicks Beach!

Cozy Ranch Home, Centrally Located near Chicks Beach!
Northwest
8.6 out of 10, Excellent, (9 reviews)
"Excellent host and a wonderful property. Great amenities and a very nice neighborhood."
United States
Peter R.
The price is AU$731
includes taxes & fees
4 Aug - 5 Aug
Cozy Ranch Home, Centrally Located near Chicks Beach!
Private kitchen

9. 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 AU$735
includes taxes & fees
5 Aug - 6 Aug
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Living area

10. 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 AU$885
includes taxes & fees
9 Aug - 10 Aug
Beautiful, spacious home in welcoming Norfolk.
Dining

11. 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 AU$1,039
includes taxes & fees
1 Sept - 2 Sept
Wooded Wonderland
Interior

12. Luxury 2-bedroom house in superb Norfolk with cool AC and charm

Luxury 2-bedroom house in superb Norfolk with cool AC and charm
Ocean View
10.0 out of 10, Exceptional, (7 reviews)
Luxury 2-bedroom house in superb Norfolk with cool AC and charm
Dining

13. Beach Bungalow King Bed 1 Floor Living

Beach Bungalow King Bed 1 Floor Living
Bayview
9.8 out of 10, Exceptional, (20 reviews)
"This was a beautiful property. Plenty of room for Family Fun and very close to the beach. The host was very helpful and communicated with us about the property. I would definitely stay here again. "
United States
Tamika H.
The price is AU$852
includes taxes & fees
3 Aug - 4 Aug
Beach Bungalow King Bed 1 Floor Living
Smart TV, fireplace, books, stereo

14. 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 AU$742
includes taxes & fees
10 Aug - 11 Aug
Unique Luxurious Waterfront in Hampton
Interior

15. 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 AU$551
includes taxes & fees
1 Sept - 2 Sept
Large 2 bedroom | Queen beds | Safe Area
TV, fireplace, video games

16. Hot Tub | 9 beds | Fenced Yard

Hot Tub | 9 beds | Fenced Yard
Downtown Hampton
5.2 out of 10, (7 reviews)
"The house served its purpose for a weekend stay. Quite a few quirks to the property. Close to downtown Hampton. "
United States
Regina P.
The price is AU$914
includes taxes & fees
4 Aug - 5 Aug
Hot Tub | 9 beds | Fenced Yard
Exterior

17. Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Coliseum Central
9.6 out of 10, Exceptional, (42 reviews)
"Another amazing stay at Jackie's place!"
United States
Sherri J.
The price is AU$791
includes taxes & fees
3 Aug - 4 Aug
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Interior

18. Sojourn Aviators Dream on Back River

Sojourn Aviators Dream on Back River
Fox Hill
9.6 out of 10, Exceptional, (30 reviews)
"We loved our stay here! The property is gorgeous, the rooms are bright and spacious, and the kitchen had everything we needed for a week long stay. The kids really loved being able to spend time in the back yard looking at the water and watching the jets fly overhead. Would definitely recommend and will rebook whenever we’re back in town! "
United States
Clare G.
The price is AU$747
includes taxes & fees
25 Aug - 26 Aug
Sojourn Aviators Dream on Back River
Beach

19. 3 bedroom home by the Sea, a block from the beach!

3 bedroom home by the Sea, a block from the beach!
Bayview
The price is AU$638
includes taxes & fees
1 Sept - 2 Sept
3 bedroom home by the Sea, a block from the beach!
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

Hampton Inn Virginia Beach-Oceanfront South

Hampton Inn Virginia Beach-Oceanfront South

10/10 Excellent
"The staff was pleasant, professional and very helpful. I love the amenities, especially the dark roast coffee. My room was great. I enjoyed the view of the beach from my room window."
Amos 2-night trip
Posted 2 hours ago
Hampton Inn Virginia Beach-Oceanfront South

Find out more about Chesapeake

Chesapeake Holiday Homes information

Number of reviews
317
Accommodation
1348 Holiday Homes
Lowest Price
AU$332
Highest Price
AU$1,039