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

Chesapeake Vacation Rentals

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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 CA $226
CA $431 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $127
CA $394 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 CA $143
CA $414 total
includes taxes & fees
Oct 7 - Oct 8
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 CA $203
CA $343 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $184
CA $498 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $442
CA $949 total
includes taxes & fees
Oct 6 - Oct 7
Wooded Wonderland
A backyard with a wooden fence, a table with chairs, and a barbecue grill.

7. 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 CA $92
CA $275 total
includes taxes & fees
Oct 16 - Oct 17
Cozy 1-bedroom barn in amazing Hampton with cool AC
A garage with a green sofa, a white table, and a patterned chair.

8. 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 CA $144
CA $284 total
includes taxes & fees
Oct 27 - Oct 28
Cozy 1-bedroom barn in marvelous Hampton with AC
A modern kitchen with white cabinets, a wooden dining table, and a blue accent wall.

9. 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 CA $228
CA $664 total
includes taxes & fees
Oct 6 - Oct 7
Beach Bungalow King Bed 1 Floor Living
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

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Bayview
8.8 out of 10, Excellent, (8 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 CA $194
CA $527 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
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, (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 CA $208
CA $612 total
includes taxes & fees
Oct 6 - Oct 7
Charming 3bd - Near beaches - Foosball & Backyard
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

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 CA $234
CA $675 total
includes taxes & fees
Oct 6 - Oct 7
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.

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 CA $205
CA $737 total
includes taxes & fees
Oct 6 - Oct 7
Unique Luxurious Waterfront in Hampton
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

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 CA $131
CA $228 total
includes taxes & fees
Oct 6 - Oct 7
bedroom house in charming E City perfect for relaxing
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!

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Willoughby Spit
9.0 out of 10, Wonderful, (7 reviews)
The price is CA $319
CA $663 total
includes taxes & fees
Oct 6 - Oct 7
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.

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 CA $139
CA $221 total
includes taxes & fees
Oct 27 - Oct 28
Small Cozy 2-bedroom house in tranquil Elizabeth City with AC. and wifi. cable
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

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 CA $210
CA $684 total
includes taxes & fees
Nov 4 - Nov 5
Sojourn Aviators Dream on Back River
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!

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Coliseum Central
9.6 out of 10, Exceptional, (44 reviews)
"Another amazing stay at Jackie's place!"
United States
Sherri J.
The price is CA $410
CA $819 total
includes taxes & fees
Oct 7 - Oct 8
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
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 CA $162
CA $393 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

Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

8/10 Good
"Great stay!"
Yitzchok 2-night trip
Posted less than an hour ago
Hyatt Place Virginia Beach / Oceanfront

Find out more about Chesapeake

Chesapeake Vacation Homes information

Number of reviews
309
Accommodation
1313 Vacation Homes
Lowest Price
CA $221
Highest Price
CA $949

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