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Search Windsor Cottage Rentals from CA $778

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Windsor cottages

House (3 Bedrooms) | Interior

1. 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 $315
CA $778 total
includes taxes & fees
Aug 4 - Aug 5
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

2. Beachwood Cottage

Beachwood Cottage
Stockbridge
9.8 out of 10, Exceptional, (6 reviews)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
United States
Christine P.
The price is CA $444
CA $838 total
includes taxes & fees
Aug 6 - Aug 7
Beachwood Cottage
Exterior

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 $2,041
CA $3,619 total
includes taxes & fees
Aug 30 - Aug 31
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 Whitlock

The Whitlock

10/10 Excellent
"a great choice if you want to stay in the heart of Lenox. It's a quiet place and had everything you needed. The people who worked there are kind. It's no frills, comfortable and affordable."
Andrew 1-night trip
Posted 9 hours ago
The Whitlock

Find out more about Windsor

Windsor Cottages information

Number of reviews
Accommodation
83 Cottages
Lowest Price
CA $778
Highest Price
CA $3,619

Frequently asked questions

How much do cottages in Windsor cost?
Cottages in Windsor range between CA $778 and CA $3,619 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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