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Our top choices for Chesapeake vacation homes
Vacation Home in Coinjock
Knot Three- Balcony View of ICW- Dog Friendly!9.6 out of 10, Exceptional, (4)
"The whole process was very easy and smooth. The property was clean and comfortable. I would definitely stay here again in the future!"
Pam P.
$198 nightly
The price is $223
Dec 20 - Dec 21
Total with taxes and fees
Vacation Home in Northeast Virginia Beach
The Art Door Duplex only minutes from beach9.6 out of 10, Exceptional, (104)
"Great get away stay! Close drive to the shops and the beach. Very cozy. Would definitely stay there again!"
Lizy G.
$189 nightly
The price is $219
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vacation Home in Portsmouth
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!9.0 out of 10, Wonderful, (22)
"Great property "
Brian C.
$248 nightly
The price is $288
Dec 21 - Dec 22
Total with taxes and fees
Vacation Home in Norfolk
10min to Ocean View: BBQ - Volleyball - Fire pit10.0 out of 10, Exceptional, (1)
"Very nice property to stay at plenty to do staying there. Good location plenty of places around for anything you may need. Host was nice and available to answer any questions I had. Would love staying there again sometime!"
Zachary C.
$283 nightly
The price is $328
Dec 22 - Dec 23
Total with taxes and fees
Vacation Home in Portsmouth
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth9.6 out of 10, Exceptional, (4)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
Paige M.
$226 nightly
The price is $263
Dec 21 - Dec 22
Total with taxes and fees
Vacation Home in Hampton
4 Bedroom Cottage - 5 Minutes from both beaches9.2 out of 10, Wonderful, (27)
"My overall stay was great! We loved the house and the host is super sweet! We had a minor issue with getting in touch with the host, but that was resolved. Definitely would book it again!"
Anonymous traveler
$430 nightly
The price is $496
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Home in Elizabeth city
Comfort near the water and University7.0 out of 10, Good, (4)
"We had a nice stay. Thank you. "
Rebecca S.
$265 nightly
The price is $299
Jan 5 - Jan 6, 2026
Total with taxes and fees
Vacation Home in Hampton
Sweet home to share with the family8.8 out of 10, Excellent, (33)
"Great place to stay"
Victor V.
$337 nightly
The price is $390
Dec 20 - Dec 21
Total with taxes and fees
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
10/10 Excellent
Find out more about Chesapeake
Chesapeake Vacation Homes information
Number of reviews | 436 |
|---|---|
Accommodation | 1390 Vacation Homes |
Lowest Price | $154 |
Highest Price | $877 |
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