Top Cottages in Isle of Wight County in 2026

A wooden boardwalk leading through a marshy landscape with a sunset in the background.

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

Top Cities in Isle of Wight County

A river curving through a landscape with dry grass fields, a dock with boats, and houses along the riverbank.

A rural road with a sign for Carrollton, a brick building, and lush greenery.

Our top choices for Isle of Wight County cottages

1. Restored 1930s Cottage on 1 Acre w/ Fire Pit

Hayes

Alena S.

AED 1,300 total

includes taxes & fees

18 Aug - 19 Aug

2. Cottage on a Private Island in the York River

Gloucester Point

Alexis P.

3. Private 1300 sq ft Cottage in Historic Yorktown-w/ trolley access

Yorktown

Lori T.

4. Historic Beach Side Getaway - Pet Friendly, Wi-Fi, Just Steps to the Beach

Willoughby Spit

Penny E N.

5. Comfortable & Private 2 Bedrm Cottage w/ King bed.

Portsmouth

Debbie M.

AED 1,304 total

includes taxes & fees

6 Sep - 7 Sep

6. Private 2,000 Sq Ft Cottage in Historic Yorktown- w/ trolley access

Yorktown

Claudia A.

7. Cozy Suite at the Beach

Willoughby Spit

Jeremy D.

8. Sandy Dunes BeachFront Cottage - Beach Front

Norfolk

Camden H.

View all properties

Find vacation rentals that suit your style

Aparthotels

Apartments

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

Top Isle of Wight County Hotel Reviews

King’s Creek Resort by Spinnaker

10/10 Excellent

"Everything in the rental was nice and clean. The check-in process was smooth. The location is ideal for folks who want to go to Water Country USA and Busch Gardens. There is lots to do on the Kings Creek property but we didn’t get a chance to take advantage of them because of our busy schedule. Maybe next time!"

Hilton Vacation Club The Historic Powhatan Williamsburg

8/10 Good

"The property overall was a good place to stay. We rented a two story, 4 bedroom townhouse with 4 bathrooms. The downstairs master bathroom was missing a shower curtain. After calling the front desk I was told that someone would be over to install a new one. After a while, I finally received a knock on the door and before I could answer it a gentleman starts to walk in carrying a bag with a curtain in it. I asked him if rings were included and he said that I just snap it on. I said "To what? There is just a rod in the bathroom.". He asked if he could see it so I showed him to which he mumbled something and said he would be back. He never returned and 4 adults had to take turns using the small bathroom in the hall that night. The next morning I went to the front desk to get a curtain and was told that they would bring one by in which I had to install. I wasn't expecting to have to install shower curtains on a place a reserved months in advance."