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

Holiday Homes in Chesapeake

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Our top choices for Chesapeake holiday homes

1. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
Chesapeake
The price is €540
includes taxes & fees
23 Nov - 24 Nov
Entire Home in Chesapeake, Virginia

2. 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, (56 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is €254
includes taxes & fees
16 Nov - 17 Nov
3-bedroom home away from home in fabulous Chesapeake, Virginia.

3. Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8

Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8
Portsmouth
9.4 out of 10, Exceptional, (8 reviews)
"There for a softball Tournament. Close to the highway easy to find"
United States
Ryan H.
The price is €280
includes taxes & fees
15 Nov - 16 Nov
Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8

4. 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
9.4 out of 10, Exceptional, (10 reviews)
"This was the perfect experience for our vacation and we highly recommend this property and the host was so easy to get in contact with!"
United States
Coachmeech Gaming O.
The price is €227
includes taxes & fees
20 Nov - 21 Nov
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

5. 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, (33 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 €249
includes taxes & fees
1 Dec - 2 Dec
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

6. 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
8.8 out of 10, Excellent, (13 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 €209
includes taxes & fees
15 Nov - 16 Nov
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

7. 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 €524
includes taxes & fees
16 Nov - 17 Nov
Wooded Wonderland

8. 3D Theater plus Dock on Small Lake

3D Theater plus Dock on Small Lake
Portsmouth
8.6 out of 10, Excellent, (4 reviews)
"Very nice property. Quiet neighborhood with a beautiful lake view."
United States
Muun Queen M.
The price is €341
includes taxes & fees
15 Nov - 16 Nov
3D Theater plus Dock on Small Lake

9. Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Norfolk
8.6 out of 10, Excellent, (93 reviews)
"Nice small rustic cottage right on the beach. Enjoyed my time there."
United States
Mary W.
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

10. Beachfront Bungalow w/ BEST Location in Ocean View!

Beachfront Bungalow w/ BEST Location in Ocean View!
Norfolk
8.4 out of 10, Very good, (28 reviews)
"Perfect place for a quiet getaway for two."
United States
Anonymous traveller
Beachfront Bungalow w/ BEST Location in Ocean View!

11. 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, (10 reviews)
"Enjoyed walking to the beach."
United States
Donna G.
The price is €321
includes taxes & fees
18 Nov - 19 Nov
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly

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

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.6 out of 10, Exceptional, (15 reviews)
"Jason made us feel welcome and the check-in process was very easy. Communication was made throughout our stay and Jason was available for anything we needed."
United States
Timothy R.
The price is €316
includes taxes & fees
16 Nov - 17 Nov
Bright 3-bedroom beach house with AC in charming Norfolk

13. Downtown Newport News | Great Area!

Downtown Newport News | Great Area!
Hudson Terrace
6.8 out of 10, (11 reviews)
"Nice check in "
United States
Brian S.
The price is €350
includes taxes & fees
12 Nov - 13 Nov
Downtown Newport News | Great Area!

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

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.8 out of 10, Exceptional, (16 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 €344
includes taxes & fees
22 Nov - 23 Nov
Charming 3bd - Near beaches - Foosball & Backyard

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

Cozy 1-bedroom barn in marvelous Hampton with AC
Hampton
10.0 out of 10, Exceptional, (2 reviews)
"It was a nice place. It was like a nice studio sized ap with a lower level living room. Very close to the university where I was at the entire weekend. The owner is nice and easy to talk to."
United States
Nicole C.
The price is €326
includes taxes & fees
12 Nov - 13 Nov
Cozy 1-bedroom barn in marvelous Hampton with AC

16. bedroom house in charming E City perfect for relaxing

bedroom house in charming E City perfect for relaxing
Elizabeth City
2.0 out of 10, (2 reviews)
"They didn't tell me they had somebody living on site until I was on my way there, between midnight and 2:30 a.m., because I told them I would be late, getting there.There was somebody else there when I got there in the room that I was supposed to be in, plus the person that lives on site.The key was where it was supposed to be, but the outside door was locked, and I rang the doorbell several times, and contacted the host, by calling and sending messages, and I still had to wait about 20 minutes...
United States
Thomas M.
The price is €137
includes taxes & fees
12 Nov - 13 Nov
bedroom house in charming E City perfect for relaxing

17. Small Cozy 2-bedroom house in tranquil Elizabeth City with AC. and wifi. cable

Small Cozy 2-bedroom house in tranquil Elizabeth City with AC. and wifi. cable
Elizabeth City
The price is €133
includes taxes & fees
8 Dec - 9 Dec
Small Cozy 2-bedroom house in tranquil Elizabeth City with AC. and wifi. cable

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

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Willoughby Spit
8.6 out of 10, Excellent, (10 reviews)
"Great house"
United States
sarah a.
The price is €386
includes taxes & fees
12 Nov - 13 Nov
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to 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

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Chesapeake Holiday Homes information

Number of reviews
205
Accommodation
1258 Holiday Homes
Lowest Price
€133
Highest Price
€540