Search Vacation Homes in Chesapeake
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chesapeake vacation homes
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, (47 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
James W.
The price is AED 786
AED 1,346 total
includes taxes & fees
29 Jun - 30 Jun
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)
"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.
The price is AED 524
AED 1,055 total
includes taxes & fees
16 Jun - 17 Jun
Cozy Beach Home in Oceanview
Cozy Beach Home in OceanviewBayview
9.8 out of 10, Exceptional, (47 reviews)
"Loved staying here. The house had everything that was needed and it was in close proximity to everything. "
Conor L.
The price is AED 643
AED 1,443 total
includes taxes & fees
11 Jun - 12 Jun
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in PortsmouthPortsmouth
9.6 out of 10, Exceptional, (4 reviews)
"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.
The price is AED 294
AED 974 total
includes taxes & fees
16 Jun - 17 Jun
Carrick Bend -Balcony View of ICW- Dog Friendly!
Carrick Bend -Balcony View of ICW- Dog Friendly!Coinjock
8.0 out of 10, Very Good, (1 review)
The price is AED 1,004
AED 1,993 total
includes taxes & fees
9 Jul - 10 Jul
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, (28 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."
Niya w.
The price is AED 371
AED 1,067 total
includes taxes & fees
15 Jun - 16 Jun
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Charming 1-bedroom in-law suite with functional kitchen in pleasant PortsmouthPortsmouth
9.4 out of 10, Exceptional, (6 reviews)
"It’s was great staying "
Shalena K.
The price is AED 551
AED 911 total
includes taxes & fees
11 Jun - 12 Jun
Beach Bungalow King Bed 1 Floor Living
Beach Bungalow King Bed 1 Floor LivingBayview
9.8 out of 10, Exceptional, (17 reviews)
"This was a beautiful property. Plenty of room for Family Fun and very close to the beach. The host was very helpful and communicated with us about the property. I would definitely stay here again. "
Tamika H.
The price is AED 774
AED 1,928 total
includes taxes & fees
15 Jun - 16 Jun
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.
Find vacation rentals that suit your style
Private vacation homes
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Chesapeake Hotel Reviews
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
8/10 Good
