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

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Our top choices for Chesapeake holiday homes

1. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
Chesapeake
The price is HK$1,106
HK$4,716 total
includes taxes & fees
9 Nov - 10 Nov
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 HK$1,179
HK$2,156 total
includes taxes & fees
4 Nov - 5 Nov
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
9.8 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 HK$698
HK$2,062 total
includes taxes & fees
20 Nov - 21 Nov
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, (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 HK$824
HK$2,216 total
includes taxes & fees
4 Nov - 5 Nov
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 HK$1,118
HK$1,796 total
includes taxes & fees
4 Nov - 5 Nov
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 HK$2,040
HK$4,589 total
includes taxes & fees
8 Nov - 9 Nov
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 HK$1,165
HK$3,068 total
includes taxes & fees
4 Nov - 5 Nov
3D Theater plus Dock on Small Lake

8. 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)
"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 HK$791
HK$2,516 total
includes taxes & fees
4 Nov - 5 Nov
Bright 3-bedroom beach house with AC in charming Norfolk

9. 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 HK$720
HK$1,186 total
includes taxes & fees
4 Nov - 5 Nov
bedroom house in charming E City perfect for relaxing

10. 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 HK$893
HK$1,874 total
includes taxes & fees
4 Nov - 5 Nov
Knot Three- Balcony View of ICW- Dog Friendly!

11. 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)
"Enjoyed walking to the beach."
United States
Donna G.
The price is HK$1,059
HK$2,811 total
includes taxes & fees
9 Nov - 10 Nov
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly

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 HK$805
HK$1,193 total
includes taxes & fees
2 Dec - 3 Dec
Small Cozy 2-bedroom house in tranquil Elizabeth City with AC. and wifi. cable

13. 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 HK$819
HK$2,879 total
includes taxes & fees
9 Nov - 10 Nov
Cozy 1-bedroom barn in marvelous Hampton with AC

14. Sojourn Aviators Dream on Back River

Sojourn Aviators Dream on Back River
Fox Hill
9.6 out of 10, Exceptional, (33 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 HK$975
HK$3,382 total
includes taxes & fees
4 Nov - 5 Nov
Sojourn Aviators Dream on Back River

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

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.8 out of 10, Exceptional, (16 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 HK$1,329
HK$3,437 total
includes taxes & fees
22 Nov - 23 Nov
Charming 3bd - Near beaches - Foosball & Backyard

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 HK$1,346
HK$3,611 total
includes taxes & fees
22 Nov - 23 Nov
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ

17. 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.
The price is HK$994
HK$3,974 total
includes taxes & fees
30 Nov - 1 Dec
Charming 1BR ViBe District bungalow with deck, WiFi, parking
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
259
Accommodation
1274 Vacation Homes
Lowest Price
HK$1,186
Highest Price
HK$4,716

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