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

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Our top choices for Chesapeake vacation homes

1. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
Chesapeake
The price is ¥23,797
¥96,928 total
includes taxes & fees
Nov 29 - Nov 30
Entire Home in Chesapeake, Virginia

2. 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 ¥24,004
¥43,901 total
includes taxes & fees
Nov 16 - Nov 17
3-bedroom home away from home in fabulous Chesapeake, Virginia.

3. 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
9.4 out of 10, Exceptional, (10 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 ¥12,793
¥40,353 total
includes taxes & fees
Nov 20 - Nov 21
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

4. 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, (33 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 ¥16,929
¥43,457 total
includes taxes & fees
Nov 30 - Dec 1
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

5. 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 ¥22,784
¥36,613 total
includes taxes & fees
Nov 20 - Nov 21
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

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 ¥41,541
¥93,983 total
includes taxes & fees
Nov 17 - Nov 18
Wooded Wonderland

7. 3D Theater plus Dock on Small Lake

3D Theater plus Dock on Small Lake
Portsmouth
8.6 out of 10, Excellent, (4 reviews)
"Very nice property. Quiet neighborhood with a beautiful lake view."
United States
Muun Queen M.
The price is ¥23,717
¥62,467 total
includes taxes & fees
Nov 15 - Nov 16
3D Theater plus Dock on Small Lake

8. 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 ¥14,230
¥20,411 total
includes taxes & fees
Dec 2 - Dec 3
Small Cozy 2-bedroom house in tranquil Elizabeth City with AC. and wifi. cable

9. 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 ¥15,971
¥58,925 total
includes taxes & fees
Nov 15 - Nov 16
Downtown Newport News | Great Area!

10. 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 ¥14,661
¥22,884 total
includes taxes & fees
Nov 15 - Nov 16
bedroom house in charming E City perfect for relaxing

11. Beach house w/BBQ, Jacuzzi & fire pit

Beach house w/BBQ, Jacuzzi & fire pit
Willoughby Spit
10.0 out of 10, Exceptional, (1 review)
"It was a nice house and not far from the beach. The house was very clean. Plenty of room for us all to be comfortable "
United States
Travis D.
The price is ¥18,675
¥64,982 total
includes taxes & fees
Nov 24 - Nov 25
Beach house w/BBQ, Jacuzzi & fire pit

12. 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, (15 reviews)
"Jason made us feel welcome and the check-in process was very easy. Communication was made throughout our stay and Jason was available for anything we needed."
United States
Timothy R.
The price is ¥19,427
¥55,455 total
includes taxes & fees
Nov 15 - Nov 16
Bright 3-bedroom beach house with AC in charming Norfolk

13. 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)
"Walking distance to a very calm and not crowded beach. Clean and well furnished cottage with new bathroom fixtures and kitchen appliances. Plenty of towels, linens, soap and shampoo, and paper goods. Would appreciate a bit more drawer space for clothes. Nice to have the covered outdoor space for all our wet and sandy beach stuff but not the most welcoming spot for outdoor dining. Owner communication was responsive and check in process was a breeze. I highly recommend this cozy cottage!"
United States
Virginia L.
The price is ¥21,585
¥57,113 total
includes taxes & fees
Nov 18 - Nov 19
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly

14. Beach Bungalow • Navy Base • Quiet St • Dogs OK

Beach Bungalow • Navy Base • Quiet St • Dogs OK
Bayview
The price is ¥22,541
¥28,605 total
includes taxes & fees
Dec 15 - Dec 16
Beach Bungalow • Navy Base • Quiet St • Dogs OK

15. Charming 1BR ViBe District bungalow with deck, WiFi, parking

Charming 1BR ViBe District bungalow with deck, WiFi, parking
Northeast Virginia Beach
9.2 out of 10, Wonderful, (39 reviews)
"This is such a cute spot to stay. It is very convenient and close enough to the oceanfront "
United States
Megan P.
Charming 1BR ViBe District bungalow with deck, WiFi, parking

16. 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 ¥27,440
¥73,041 total
includes taxes & fees
Nov 15 - Nov 16
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ

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

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.8 out of 10, Exceptional, (17 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 ¥27,885
¥67,996 total
includes taxes & fees
Nov 22 - Nov 23
Charming 3bd - Near beaches - Foosball & Backyard

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 ¥19,882
¥40,245 total
includes taxes & fees
Nov 15 - Nov 16
Knot Three- Balcony View of ICW- Dog Friendly!

19. 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, (2 reviews)
"It was a nice place. It was like a nice studio sized ap with a lower level living room. Very close to the university where I was at the entire weekend. The owner is nice and easy to talk to."
United States
Nicole C.
The price is ¥16,099
¥57,956 total
includes taxes & fees
Nov 17 - Nov 18
Cozy 1-bedroom barn in marvelous Hampton with AC

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, (44 reviews)
"Lovely, comfortable waterside home. Thank you for your hospitality!"
United States
Mary P.
The price is ¥18,111
¥51,032 total
includes taxes & fees
Nov 22 - Nov 23
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

Find out more about Chesapeake

Chesapeake Vacation Homes information

Number of reviews
268
Accommodation
1258 Vacation Homes
Lowest Price
¥20,411
Highest Price
¥96,928