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$2,341 total

includes taxes & fees

21 Oct - 22 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

Coachmeech Gaming O.

HK$2,064 total

includes taxes & fees

20 Oct - 21 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$2,262 total

includes taxes & fees

14 Oct - 15 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

14 Oct - 15 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$2,740 total

includes taxes & fees

21 Oct - 22 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$5,217 total

includes taxes & fees

14 Oct - 15 Oct

A compact laundry room with a washing machine and dryer, a small shelf with a bottle, and a window with a view.

7. ODU Cozy Cottage with river views near bars, grills, brewery! 2 br/1 bath house!

Norfolk

Anonymous traveller

A pool table in a room with wooden floors, a fireplace, and a window with purple curtains.

8. Centrally Located Hampton Roads Home w/ Game Room!

Portsmouth

Elaine P.

HK$4,906 total

includes taxes & fees

5 Nov - 6 Nov

A backyard with a wooden fence, a table with chairs, and a barbecue grill.

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

Hampton

HK$1,656 total

includes taxes & fees

19 Oct - 20 Oct

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

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

Hampton

HK$1,575 total

includes taxes & fees

19 Oct - 20 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$3,370 total

includes taxes & fees

19 Oct - 20 Oct

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

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

Bayview

Todd C.

HK$2,939 total

includes taxes & fees

2 Nov - 3 Nov

A beach with a wooden picnic table and a barbecue grill, surrounded by greenery and leading to the ocean.

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

Norfolk

Benjamin C.

HK$2,443 total

includes taxes & fees

14 Oct - 15 Oct

A modern interior with a staircase, a door with a decorative glass panel, and a hallway with a tiled floor.

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

Willoughby Spit

Sheryll

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

15. Beach Bungalow King Bed 1 Floor Living

Bayview

Thomas M.

HK$3,622 total

includes taxes & fees

14 Oct - 15 Oct

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

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

Cottage Park

Robin T.

HK$3,680 total

includes taxes & fees

14 Oct - 15 Oct

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

17. Unique Luxurious Waterfront in Hampton

Hampton

WILLIAM M.

HK$4,091 total

includes taxes & fees

19 Oct - 20 Oct

A spacious living room with a white sofa, a teal sectional, and a patterned rug.

18. Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard

Bayview

Nate K.

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

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

Willoughby Spit

HK$3,616 total

includes taxes & fees

14 Oct - 15 Oct

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

20. 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$1,258 total

includes taxes & fees

14 Oct - 15 Oct

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Top Chesapeake Hotel Reviews

Hilton Vacation Club Oceanaire Virginia Beach

10/10 Excellent

"Great view of the ocean. Sunrise and sunset. Very clean we’ll stay again."

Crowne Plaza Virginia Beach Town Center by IHG

10/10 Excellent

"My husband and I stayed for 2 nights and had a great visit. The hotel is close to the highway, Mount Trashmore and Town Center making very convenient for visitors. The staff was very pleasant and helpful. They have a restaurant in the hotel where we both enjoyed dinner one evening. The room was clean and the bed was more comfortable than we expected, which was a pleasant surprise. There were only two things I would alert others to before booking. We didn’t pay attention that there was not a microwave in the room while booking. This wasn’t a big deal for us but might be for others. And our room faced the highway so if you’re a light sleeper you might want to ask for a room on the opposite side. Neither were deal breakers for us. I would definitely recommend this hotel."

Comfort Inn & Suites Hampton near Coliseum

10/10 Excellent

"Liked that room was clean & had fridge & microwave, large bathroom with middle area that did not steam over so could see visibly, comfortable chair with slide table as well as desk & chair separate. Had plenty of room & hangers for hanging clothes. Loved had 2 spots for our luggage to keep off floor, usually that’s where my husband has to keep his. Only negative was out of ice on first 2 floors."

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