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Search Windsor Cottage Rentals from CA $783

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Windsor cottages

A wooden deck with a table, benches, and outdoor furniture.

1. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

The Cottage on Mill Brook is walking distance to Berkshire East and the River.
Charlemont
The price is CA $505
CA $783 total
includes taxes & fees
Nov 17 - Nov 18
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
A cabin with a wooden deck, a covered porch, and a gravel driveway.

2. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is CA $355
CA $822 total
includes taxes & fees
Nov 3 - Nov 4
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A two-story house with a balcony, a chimney, and a window with a view.

3. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is CA $1,256
CA $2,711 total
includes taxes & fees
Nov 18 - Nov 19
Berkshires farm, 30+ guests, 50 acres
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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Top Windsor Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Very charming, particularly the main house. We were at another structure off the main place which was perfectly nice but perhaps less charming."
Diane 1-night trip
Posted 11 hours ago
The Red Lion Inn

Find out more about Windsor

Windsor Cottages information

Number of reviews
Accommodation
67 Cottages
Lowest Price
CA $783
Highest Price
CA $2,711

Frequently asked questions

How much do cottages in Windsor cost?
Cottages in Windsor range between CA $783 and CA $2,711 per night. These properties offer a chance to soak up nature's beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Windsor with Expedia?
Expedia has some wonderful cottages in Windsor, so start packing your bags for a memorable vacation on nature's doorstep. If you have a budget in mind, select how much you'd like to spend and the star rating of your property. Or take advantage of our filters to search for cottages with free WiFi or a pool. We'll help you find the right digs whatever your plans or bank balance.
How can I find cheap cottages in Windsor?
Expedia is here to help you easily locate cheap cottages in Windsor. To reserve a fantastic stay in a few quick keystrokes, try out the filter tool to refine your search results by amenities, star rating and budget.

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