Chesapeake Vacation Homes

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search 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 holiday homes

3-bedroom home away from home in fabulous Chesapeake, Virginia.

Chesapeake

James W.

HK$2,497 total

includes taxes & fees

8 Jun - 9 Jun

Knot Three- Balcony View of ICW- Dog Friendly!

Coinjock

Pam P.

HK$2,155 total

includes taxes & fees

1 Jun - 2 Jun

Welcoming 2-bedroom house in charming Elizabeth City perfect for relaxing

Elizabeth City

HK$1,256 total

includes taxes & fees

31 May - 1 Jun

Cozy 2-bedroom house in tranquil Elizabeth City with AC. Kick back with us.

Elizabeth City

HK$1,342 total

includes taxes & fees

31 May - 1 Jun

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Portsmouth

Niya w.

HK$2,375 total

includes taxes & fees

3 Jun - 4 Jun

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

Willoughby Spit

Sheila H.

HK$2,304 total

includes taxes & fees

31 May - 1 Jun

Beach Bungalow King Bed 1 Floor Living

Bayview

Tamika H.

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Portsmouth

Shalena K.

HK$1,943 total

includes taxes & fees

31 May - 1 Jun

View all properties

Find holiday rentals that suit your style

Aparthotels

Condos

Save an average of 15% on thousands of hotels when you're signed in

Top Chesapeake Hotel Reviews

Ocean Resort

6/10 Okay

"Our initial impression wasn’t the best. The lobby and elevators were dirty. The stay was nice."

Wingate by Wyndham Chesapeake

2/10 Terrible

"The only good thing about this trip was the young lady who worked at the front desk. The room was old and dated and had a smell, we were supposed to have a dining room table and it was a folding table. Half of the outlets didn’t work, the bathroom was kept up well but everything was either peeling or covered in plaster. The front desk area is the only thing that looks maintained. The pool was closed. I’ve stayed at the Wingate in Short Pump and it’s very nice and the folks are hospitable, the gentleman who works Saturday nights was very rude and could not even help us with the Wi-Fi that didn’t work also. Just a truly awful experience that has turned me off from Wingate altogether."

Coastal Hotel and Suites Virginia Beach Oceanfront

10/10 Excellent

"A one hour early check-in is usually doable by the staff in most instances, mainly during the week. Weekends gets harder as the hotel really fills up. All rooms are oceanfront with a great view right on the boardwalk. Room size is much better than most hotels. Rooms are comfortable and clean. Staff is friendly and most helpful. A great place to stay when visiting Virginia Beach by yourself, with a loved one, or with your whole family."

Find out more about Chesapeake