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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 $216
CA $415 total
includes taxes & fees
Nov 4 - Nov 5
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 $112
CA $373 total
includes taxes & fees
Nov 1 - Nov 2
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, (32 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 $151
CA $425 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $200
CA $340 total
includes taxes & fees
Nov 4 - Nov 5
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, (49 reviews)
"The location suited our business travel needs. Never received checkin details so had to call. WiFi did not work and no response to multiple inquiries about the issue. Areas of damage throughout the house."
United States
Jebediah
The price is CA $181
CA $491 total
includes taxes & fees
Oct 26 - Oct 27
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 $364
CA $869 total
includes taxes & fees
Oct 26 - Oct 27
Wooded Wonderland
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

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.6 out of 10, Exceptional, (14 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 CA $141
CA $472 total
includes taxes & fees
Oct 26 - Oct 27
Bright 3-bedroom beach house with AC in charming Norfolk
A modern kitchen with white cabinets, stainless steel appliances, and a large island with bar stools.

8. 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 CA $204
CA $601 total
includes taxes & fees
Oct 26 - Oct 27
Charming 3bd - Near beaches - Foosball & Backyard
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

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 CA $189
CA $524 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
A modern kitchen with white cabinets, a wooden dining table, and a blue accent wall.

10. 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 $224
CA $658 total
includes taxes & fees
Oct 26 - Oct 27
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.

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

Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
Cottage Park
9.2 out of 10, Wonderful, (7 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 $230
CA $663 total
includes taxes & fees
Oct 26 - Oct 27
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
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

Small Cozy 2-bedroom house in tranquil Elizabeth City with AC. and wifi. cable
Elizabeth City
The price is CA $146
CA $228 total
includes taxes & fees
Oct 26 - Oct 27
Small Cozy 2-bedroom house in tranquil Elizabeth City with AC. and wifi. cable
A single-story house with a front porch, a number '605' on the door, and a small front yard with a pathway leading to the entrance.

13. 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 $129
CA $224 total
includes taxes & fees
Oct 29 - Oct 30
bedroom house in charming E City perfect for relaxing
A bathroom with a shower curtain, a towel rack with towels, and a toilet paper holder.

14. 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 $141
CA $536 total
includes taxes & fees
Oct 26 - Oct 27
Cozy 1-bedroom barn in marvelous Hampton with AC
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

Unique Luxurious Waterfront in Hampton
Hampton
9.6 out of 10, Exceptional, (4 reviews)
"Great value for the money, great hosts, very renter friendly"
United States
WILLIAM M.
The price is CA $214
CA $745 total
includes taxes & fees
Nov 3 - Nov 4
Unique Luxurious Waterfront in Hampton
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

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 $174
CA $644 total
includes taxes & fees
Oct 26 - Oct 27
Sojourn Aviators Dream on Back River
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!

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 $314
CA $652 total
includes taxes & fees
Nov 1 - Nov 2
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
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!

Knot Three- Balcony View of ICW- Dog Friendly!
Coinjock
8.4 out of 10, Very good, (6 reviews)
"Nice! "
United States
Sawyer P.
The price is CA $148
CA $339 total
includes taxes & fees
Oct 26 - Oct 27
Knot Three- Balcony View of ICW- Dog Friendly!
A single-story house with a front porch, a small staircase, and a visible garage door.

19. Downtown Newport News | Great Area!

Downtown Newport News | Great Area!
Hudson Terrace
6.8 out of 10, (11 reviews)
"Nice check in "
United States
Brian S.
The price is CA $221
CA $667 total
includes taxes & fees
Oct 27 - Oct 28
Downtown Newport News | Great Area!
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

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 $159
CA $476 total
includes taxes & fees
Oct 28 - Oct 29
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

Boardwalk Resort and Villas

Boardwalk Resort and Villas

10/10 Excellent
"It was great, only thing I don't like is the garage in the parking is awful. And having breakfast available at the hotel would be fantastic!"
Becky 1-night trip
Posted 2 hours ago
Boardwalk Resort and Villas

Find out more about Chesapeake

Chesapeake Vacation Homes information

Number of reviews
344
Accommodation
1258 Vacation Homes
Lowest Price
CA $224
Highest Price
CA $869

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