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

Search Vacation Homes in Chesapeake

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 AED 582
AED 1,103 total
includes taxes & fees
21 Oct - 22 Oct
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 AED 294
AED 966 total
includes taxes & fees
20 Oct - 21 Oct
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, (31 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 AED 367
AED 1,059 total
includes taxes & fees
14 Oct - 15 Oct
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, (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 AED 523
AED 883 total
includes taxes & fees
14 Oct - 15 Oct
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

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

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.0 out of 10, Very good, (48 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
The price is AED 474
AED 1,270 total
includes taxes & fees
11 Nov - 12 Nov
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

6. 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 AED 1,140
AED 2,442 total
includes taxes & fees
14 Oct - 15 Oct
Wooded Wonderland
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!

ODU Cozy Cottage with river views near bars, grills, brewery! 2 br/1 bath house!
Norfolk
10.0 out of 10, Exceptional, (1 review)
"Great stay"
United States
Anonymous traveler
ODU Cozy Cottage with river views near bars, grills, brewery! 2 br/1 bath house!
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!

Centrally Located Hampton Roads Home w/ Game Room!
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very nice! And the host was in full contact with us throughout our stay to make sure we had everything we needed. Also, our family LOVED the video games. "
United States
Elaine P.
The price is AED 867
AED 2,296 total
includes taxes & fees
5 Nov - 6 Nov
Centrally Located Hampton Roads Home w/ Game Room!
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

Cozy 1-bedroom barn in amazing Hampton with cool AC
Hampton
10.0 out of 10, Exceptional, (5 reviews)
Cozy 1-bedroom barn in amazing Hampton with cool AC
A garage with a green sofa, a white table, and a patterned chair.

10. 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)
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.

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

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.6 out of 10, Exceptional, (15 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 AED 536
AED 1,577 total
includes taxes & fees
19 Oct - 20 Oct
Charming 3bd - Near beaches - Foosball & Backyard
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

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 AED 496
AED 1,375 total
includes taxes & fees
2 Nov - 3 Nov
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
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!

Beachfront Bungalow w/ BEST Location in Ocean View!
Norfolk
8.4 out of 10, Very good, (28 reviews)
"Great host and great property! Will be coming back in the future! Loved the fire pit feet from the beach!!"
United States
Benjamin C.
Beachfront Bungalow w/ BEST Location in Ocean View!
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

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.6 out of 10, Exceptional, (13 reviews)
"The property is spacious and conveniently located near the beach and restaurants. It is family-friendly and the host is exceptionally communicative. I plan to return in the future."
United States
Sheryll
The price is AED 430
AED 1,314 total
includes taxes & fees
18 Oct - 19 Oct
Bright 3-bedroom beach house with AC in charming Norfolk
A modern kitchen with white cabinets, a wooden dining table, and a blue accent wall.

15. 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 AED 588
AED 1,721 total
includes taxes & fees
14 Oct - 15 Oct
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.

16. 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 AED 603
AED 1,743 total
includes taxes & fees
14 Oct - 15 Oct
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
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

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 AED 542
AED 1,915 total
includes taxes & fees
19 Oct - 20 Oct
Unique Luxurious Waterfront in Hampton
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

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 AED 685
AED 1,981 total
includes taxes & fees
25 Oct - 26 Oct
Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard
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!

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Willoughby Spit
9.0 out of 10, Wonderful, (7 reviews)
The price is AED 823
AED 1,718 total
includes taxes & fees
14 Oct - 15 Oct
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.

20. 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 AED 337
AED 589 total
includes taxes & fees
14 Oct - 15 Oct
bedroom house in charming E City perfect for relaxing
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesapeake Hotel Reviews

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

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

10/10 Excellent
"Great place"
Sam 1-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)