Search Jamestown Island Cottage Rentals from CA $186

  • 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

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
apart-hotel image
Aparthotels
Aparthotels

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Jamestown Island cottages

A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

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

Restored 1930s Cottage on 1 Acre w/ Fire Pit
Hayes
9.6 out of 10, Exceptional, (97 reviews)
"Our family of 6 (age range 20’s to 80’s) enjoyed all of the rooms and porches. The air conditioners kept the home comfortable and the porches were cozy for those who like it warmer. We liked the convenience of being able to make our own breakfasts and dinners here. Having a grill was a bonus."
United States
Susan C.
The price is CA $186
CA $494 total
includes taxes & fees
Nov 10 - Nov 11
Restored 1930s Cottage on 1 Acre w/ Fire Pit
A single-story house with a front porch, a small deck, and a driveway leading to the entrance.

2. Williamsburg Home for Colonial & Theme Park Trips

Williamsburg Home for Colonial & Theme Park Trips
3.0 star property
Williamsburg
The price is CA $558
CA $1,015 total
includes taxes & fees
Nov 21 - Nov 22
Williamsburg Home for Colonial & Theme Park Trips
A house with a large lawn, surrounded by tall trees.

3. Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown

Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
Hayes
8.4 out of 10, Very good, (5 reviews)
"Great property. Waterfront with pier, huge yard, beautiful home with pool table, hot tub and projector set up. 100% would stay here again and recommend as would all of the family we had stay or visit us there. "
United States
Steve F.
The price is CA $346
CA $1,698 total
includes taxes & fees
Nov 10 - Nov 11
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
A single-story house with a brick exterior, a covered porch with blue chairs, and a brick pathway leading to the entrance.

4. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
3.0 star property
Gloucester
The price is CA $239
CA $506 total
includes taxes & fees
Nov 10 - Nov 11
Radiant Gloucester House w/ Private Porch!
A large house with a front porch, surrounded by trees and a gravel driveway.

5. Located in the Heart of Gloucester Courthouse!

Located in the Heart of Gloucester Courthouse!
3.0 star property
Gloucester
The price is CA $247
CA $516 total
includes taxes & fees
Nov 12 - Nov 13
Located in the Heart of Gloucester Courthouse!
A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

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

Restored 1930s Cottage on 1 Acre w/ Fire Pit
3.0 star property
Hayes
The price is CA $247
CA $506 total
includes taxes & fees
Nov 10 - Nov 11
Restored 1930s Cottage on 1 Acre w/ Fire Pit
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.
View all properties

Learn more about Jamestown Island

Explore attractions like Historic Jamestowne and Colonial National Historical Park as you discover things to see and do in Jamestown Island.

See all hotels in Jamestown Island
A historic brick church with arched windows and a steeply pitched roof, surrounded by a grassy area and trees.

Top reviews in Jamestown Island

A Hampton Inn & Suites hotel with a symmetrical facade, multiple windows, and a flagpole with flags.
Hampton Inn & Suites Williamsburg-Richmond Rd.

Hampton Inn & Suites Williamsburg-Richmond Rd.

Hampton Inn & Suites Williamsburg-Richmond Rd.
Williamsburg

10/10 Excellent

Very well located to great restaurants and easy area to get around.
Canada
John
Reviewed April 2, 2026
Hampton Inn & Suites Williamsburg-Richmond Rd.

Explore a world of travel with Expedia