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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chesapeake vacation 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, (56 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is ￥24,601
￥46,598 total
includes taxes & fees
Oct 13 - Oct 14
3-bedroom home away from home in fabulous Chesapeake, Virginia.
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

2. 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)
"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 ￥12,648
￥41,529 total
includes taxes & fees
Oct 20 - Oct 21
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in 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 ￥15,790
￥45,507 total
includes taxes & fees
Nov 9 - Nov 10
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A living room with a beige sofa, a white ottoman, a patterned rug, a wooden chair, and a small table.

4. 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, (12 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 ￥22,501
￥37,974 total
includes taxes & fees
Oct 12 - Oct 13
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A spacious living room with a stone fireplace, a flat-screen TV, a ceiling fan, and a dining area with a table and chairs.

5. 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 ￥49,028
￥105,703 total
includes taxes & fees
Oct 11 - Oct 12
Wooded Wonderland
A backyard with a wooden fence, a table with chairs, and a barbecue grill.

6. 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, (5 reviews)
The price is ￥10,232
￥30,697 total
includes taxes & fees
Oct 20 - Oct 21
Cozy 1-bedroom barn in amazing Hampton with cool AC
A garage with a green sofa, a white table, and a patterned chair.

7. 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, (1 review)
The price is ￥15,926
￥31,713 total
includes taxes & fees
Nov 3 - Nov 4
Cozy 1-bedroom barn in marvelous Hampton with AC
A modern kitchen with white cabinets, stainless steel appliances, and a large island with bar stools.

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

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.6 out of 10, Exceptional, (14 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 ￥23,022
￥67,624 total
includes taxes & fees
Oct 21 - Oct 22
Charming 3bd - Near beaches - Foosball & Backyard
A kitchen with a wooden island, bar stools, a ceiling fan, and a refrigerator.

9. 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)
"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 ￥21,330
￥58,800 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
A modern kitchen with white cabinets, a wooden dining table, and a blue accent wall.

10. 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 ￥25,280
￥73,650 total
includes taxes & fees
Oct 12 - Oct 13
Beach Bungalow King Bed 1 Floor Living
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 ￥25,937
￥74,089 total
includes taxes & fees
Oct 14 - Oct 15
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
A spacious living room with a white sofa, a teal sectional, and a patterned rug.

12. 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, (25 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 ￥32,529
￥88,546 total
includes taxes & fees
Oct 25 - Oct 26
Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard
A modern interior with a staircase leading to a second floor, a living area with a grey sofa, and a kitchen with wooden cabinets.

13. Unique Luxurious Waterfront in Hampton

Unique Luxurious Waterfront in Hampton
Hampton
10.0 out of 10, Exceptional, (3 reviews)
"Great value for the money, great hosts, very renter friendly"
United States
WILLIAM M.
The price is ￥23,590
￥82,645 total
includes taxes & fees
Oct 19 - Oct 20
Unique Luxurious Waterfront in Hampton
A waterfront view from a wooden deck with a white railing, a dock extending into the water, and a clear blue sky.

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

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Willoughby Spit
9.0 out of 10, Wonderful, (7 reviews)
The price is ￥35,385
￥73,306 total
includes taxes & fees
Oct 13 - Oct 14
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
A two-story building with a balcony, a satellite dish, and a small garden area.

15. 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 ￥14,495
￥25,302 total
includes taxes & fees
Oct 14 - Oct 15
bedroom house in charming E City perfect for relaxing
A two-story building with a balcony, a satellite dish, and a small garden area.

16. 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 ￥15,064
￥24,159 total
includes taxes & fees
Oct 26 - Oct 27
Small Cozy 2-bedroom house in tranquil Elizabeth City with AC. and wifi. cable
A balcony with a table and two chairs, overlooking a body of water with boats and buildings in the background.

17. Knot Three- Balcony View of ICW- Dog Friendly!

Knot Three- Balcony View of ICW- Dog Friendly!
Coinjock
8.4 out of 10, Very good, (6 reviews)
"Nice! "
United States
Sawyer P.
Knot Three- Balcony View of ICW- Dog Friendly!
A view through a window with a grid pattern, overlooking a calm sea and a sandy beach with a small structure and a lifebuoy.

18. Sojourn Aviators Dream on Back River

Sojourn Aviators Dream on Back River
Fox Hill
9.8 out of 10, Exceptional, (32 reviews)
"Great location. Excellent view. The F22 Raptors were cool to see. Not so loud. Host was great. The place does not have a full size oven, so plan accordingly. Beds were comfy."
United States
Jim G.
The price is ￥20,737
￥73,506 total
includes taxes & fees
Nov 2 - Nov 3
Sojourn Aviators Dream on Back River
A room with a large window offering a view of trees and a body of water.

19. Waterview Cottage on the Currituck Sound with Private Dock & Kayaks

Waterview Cottage on the Currituck Sound with Private Dock & Kayaks
Coinjock
10.0 out of 10, Exceptional, (43 reviews)
"Lovely, comfortable waterside home. Thank you for your hospitality!"
United States
Mary P.
The price is ￥17,917
￥43,004 total
includes taxes & fees
Oct 13 - Oct 14
Waterview Cottage on the Currituck Sound with Private Dock & Kayaks
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

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

8/10 Good
"We loved the oceanfront balcony but would have liked to have a small table between the 2 chairs. The walk-in shower is great, but as seniors would like a safety bar on the shower wall for additional security. These are only suggestions for seniors accessibility rooms. Would return for another vacation. Thanke"
Mary G. 3-night trip
Posted 6 hours ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Find out more about Chesapeake

Chesapeake Vacation Homes information

Number of reviews
298
Accommodation
1296 Vacation Homes
Lowest Price
￥24,159
Highest Price
￥105,703