Chesapeake Vacation Homes

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

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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.

Chesapeake

James W.

HK$2,297 total

includes taxes & fees

4 Nov - 5 Nov

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

Portsmouth

Coachmeech Gaming O.

HK$2,063 total

includes taxes & fees

1 Nov - 2 Nov

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!!

Portsmouth

Niya w.

HK$2,341 total

includes taxes & fees

16 Nov - 17 Nov

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

Portsmouth

Kimberly

HK$1,886 total

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

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

Portsmouth

Jebediah

HK$2,729 total

includes taxes & fees

26 Oct - 27 Oct

A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

6. Wooded Wonderland

Portsmouth

Erin W.

HK$4,804 total

includes taxes & fees

25 Oct - 26 Oct

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

Willoughby Spit

Sheryll

HK$2,642 total

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with white cabinets, stainless steel appliances, and a large island with bar stools.

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

Bayview

Debbie M.

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

Bayview

Todd C.

HK$2,937 total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with white cabinets, a wooden dining table, and a blue accent wall.

10. Beach Bungalow King Bed 1 Floor Living

Bayview

Thomas M.

HK$3,657 total

includes taxes & fees

25 Oct - 26 Oct

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

Cottage Park

Robin T.

HK$3,705 total

includes taxes & fees

27 Oct - 28 Oct

A single-story house with a front porch, a door with a number '605' above it, and a small garden area with potted plants and flowers.

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

Elizabeth City

HK$1,280 total

includes taxes & fees

26 Oct - 27 Oct

A two-story building with a balcony, a satellite dish, and a small garden area.

13. bedroom house in charming E City perfect for relaxing

Elizabeth City

"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...

Thomas M.

HK$1,256 total

includes taxes & fees

25 Oct - 26 Oct

A bedroom with a bed, dresser, and a desk with a computer.

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

Hampton

HK$3,073 total

includes taxes & fees

31 Oct - 1 Nov

A modern interior with a staircase leading to a second floor, a living area with a grey sofa, and a kitchen with wooden cabinets.

15. Unique Luxurious Waterfront in Hampton

Hampton

WILLIAM M.

HK$4,146 total

includes taxes & fees

3 Nov - 4 Nov

A view through a window with a grid pattern, overlooking a calm sea and a sandy beach with a small structure and a lifebuoy.

16. Sojourn Aviators Dream on Back River

Fox Hill

Jim G.

HK$3,579 total

includes taxes & fees

26 Oct - 27 Oct

A waterfront view from a wooden deck with a white railing, a dock extending into the water, and a clear blue sky.

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

Willoughby Spit

HK$3,614 total

includes taxes & fees

25 Oct - 26 Oct

A balcony with a table and two chairs, overlooking a body of water with boats and buildings in the background.

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

Coinjock

Sawyer P.

HK$1,878 total

includes taxes & fees

25 Oct - 26 Oct

A single-story house with a front porch, a small staircase, and a visible garage door.

19. Downtown Newport News | Great Area!

Hudson Terrace

Brian S.

HK$3,796 total

includes taxes & fees

26 Oct - 27 Oct

A room with a large window offering a view of trees and a body of water.

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

Coinjock

Mary P.

HK$2,665 total

includes taxes & fees

28 Oct - 29 Oct

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Top Chesapeake Hotel Reviews

Hilton Vacation Club Ocean Beach Club Virginia Beach

8/10 Good

"The property was fairly clean and well-kept. There is a convenient parking garage nearby, and they give you a free code to access it. They do try to sell you on vacation packages, but they accept it when you decline politely."

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