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$2,357 total

includes taxes & fees

5 Oct - 6 Oct

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

Paige M.

HK$2,153 total

includes taxes & fees

25 Oct - 26 Oct

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$2,261 total

includes taxes & fees

13 Oct - 14 Oct

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$1,887 total

includes taxes & fees

5 Oct - 6 Oct

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

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

Portsmouth

John B.

HK$2,748 total

includes taxes & fees

5 Oct - 6 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$5,253 total

includes taxes & fees

6 Oct - 7 Oct

A compact room with a teal sofa, a white table, and a black chair.

7. Cozy 1-bedroom barn in amazing Hampton with cool AC

Hampton

HK$1,525 total

includes taxes & fees

16 Oct - 17 Oct

A garage with a green sofa, a white table, and a patterned chair.

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

Hampton

HK$1,566 total

includes taxes & fees

26 Oct - 27 Oct

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

9. Beach Bungalow King Bed 1 Floor Living

Bayview

Thomas M.

A kitchen with a wooden island, bar stools, a ceiling fan, and a refrigerator.

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

Bayview

Todd C.

HK$3,002 total

includes taxes & fees

26 Oct - 27 Oct

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

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

Bayview

Debbie M.

HK$3,474 total

includes taxes & fees

6 Oct - 7 Oct

A sunlit room with a ceiling fan, two wicker chairs with cushions, a striped rug, and a small table with a plant.

12. Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ

Cottage Park

Robin T.

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

Hampton

WILLIAM M.

HK$4,047 total

includes taxes & fees

6 Oct - 7 Oct

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

14. 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$1,257 total

includes taxes & fees

4 Oct - 5 Oct

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

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

Willoughby Spit

HK$3,661 total

includes taxes & fees

5 Oct - 6 Oct

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

Elizabeth City

HK$1,272 total

includes taxes & fees

13 Oct - 14 Oct

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

17. Sojourn Aviators Dream on Back River

Fox Hill

Jim G.

HK$3,728 total

includes taxes & fees

27 Oct - 28 Oct

A two-story house with a porch, a covered front entry, and a small front yard with landscaping.

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

Coliseum Central

Sherri J.

HK$5,005 total

includes taxes & fees

1 Nov - 2 Nov

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

Coinjock

Mary P.

HK$2,159 total

includes taxes & fees

13 Oct - 14 Oct

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Top Chesapeake Hotel Reviews

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

10/10 Excellent

"Staff was incredibly helpful. Location was perfect. Pool was wonderful. Coffee and light bite was very much appreciated."

Schooner Inn

8/10 Good

"We had a wonderful time at this property! Waking up to the sunrise was absolutely breath-taking. The staff was great!! Very attentive and helpful throughout our stay. I will definitely stay here again! I would have given 5 stars, but the property is a bit dated. I believe that they are replacing mattresses, but ours was still very lumpy and somewhat uncomfortable. Overall, this is a great place to stay with direct access to the beach. We will definitely stay here again!"

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