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Find vacation rentals that suit your style

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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 Gloucester cottages

A single-story house with a brick exterior, a covered porch with blue chairs, and a brick pathway leading to the entrance.

1. Radiant Gloucester House w/ Private Porch!

Radiant Gloucester House w/ Private Porch!
3.0 star property
Gloucester
$322 nightly
The price is $358
Nov 12 - Nov 13
Total with taxes and fees
Radiant Gloucester House w/ Private Porch!
A large house with a front porch, surrounded by trees and a gravel driveway.

2. Located in the Heart of Gloucester Courthouse!

Located in the Heart of Gloucester Courthouse!
3.0 star property
Gloucester
$328 nightly
The price is $365
Nov 12 - Nov 13
Total with taxes and fees
Located in the Heart of Gloucester Courthouse!
A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

3. 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.
$314 nightly
The price is $349
Nov 22 - Nov 23
Total with taxes and fees
Restored 1930s Cottage on 1 Acre w/ Fire Pit
A covered porch with wooden benches and chairs, large windows, and a view of a grassy area.

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

Restored 1930s Cottage on 1 Acre w/ Fire Pit
3.0 star property
Hayes
$322 nightly
The price is $358
Nov 22 - Nov 23
Total with taxes and fees
Restored 1930s Cottage on 1 Acre w/ Fire Pit
A white house with a black front door, a small porch, and a gravel driveway.

5. Bay Dream Believer Cottage on Beautiful East River Waterfront

Bay Dream Believer Cottage on Beautiful East River Waterfront
Mathews
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful location, host communicated well"
United States
Nicole K.
$412 nightly
The price is $454
Nov 12 - Nov 13
Total with taxes and fees
Bay Dream Believer Cottage on Beautiful East River Waterfront
A covered outdoor seating area with wicker furniture and red cushions, overlooking a lake and dock.

6. Riverfront Cottage: Fire Pit & Kayaks

Riverfront Cottage: Fire Pit & Kayaks
Deltaville
9.8 out of 10, Exceptional, (52 reviews)
"This place was a perfect getaway. Quiet and a beautiful view!"
United States
David P.
$358 nightly
The price is $395
Nov 23 - Nov 24
Total with taxes and fees
Riverfront Cottage: Fire Pit & Kayaks
A house with a large lawn, surrounded by tall trees.

7. 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.
$1,080 nightly
The price is $1,202
Nov 12 - Nov 13
Total with taxes and fees
Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown
A single-story house with a front porch, a small deck, and a driveway leading to the entrance.

8. Williamsburg Home for Colonial & Theme Park Trips

Williamsburg Home for Colonial & Theme Park Trips
3.0 star property
Williamsburg
$640 nightly
The price is $718
Nov 21 - Nov 22
Total with taxes and fees
Williamsburg Home for Colonial & Theme Park Trips
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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Learn more about Gloucester

Dive into history at the Gloucester Museum before exploring the haunting Rosewell Ruins. Paddle through Beaverdam Park's tranquil waters or ask locals about hidden swimming spots in Middle Peninsula State Park.

See all hotels in Gloucester
A steel bridge over a calm river with a sandy beach and rocky outcrops on the right.

Top reviews in Gloucester

A large white house with a dark roof, multiple chimneys, and a white fence in the foreground.
Warner Hall

Warner Hall

Warner Hall
Gloucester

10/10 Excellent

The “resting place” to go to! Need a small Keurig coffee machine and refrigerator in the rooms would be greatly appreciated! The new restaurant and bar added to the place was a very big plus!
United States
Joseph
Reviewed November 10, 2026
Warner Hall

Frequently Asked Questions

Why book your cottage in Gloucester with Expedia?

Booking a cottage in Gloucester is as easy as working out your travel dates and choosing an ideal place for outdoor relaxation and recreation. From high-end retreats to inexpensive properties and cottages that offer amenities like laundry facilities, Expedia has something for all traveler styles. As for the best offers around? We've have them as well!

How can I find cheap cottages in Gloucester?

With Expedia's filter tool, comparing cheap cottages in Gloucester has never been simpler. To discover stays that'll make your wallet smile, refine your search results by amenities, star rating and budget.

What is there to do in Gloucester near my cottage?

The ultimate travel accessory is a well-thought-out travel plan. Gloucester Museum of History is a great place to start your adventures in Gloucester.

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