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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Windsor cottages

Exterior

1. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
$2,369 nightly
The price is $2,404
Sep 2 - Sep 3
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres
House (3 Bedrooms) | Interior

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
$499 nightly
The price is $554
Aug 4 - Aug 5
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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
"The inn, located in the center of Lenox, has a lot of historical character. It feels like a classic new England inn."
James 1-night trip
Posted less than an hour ago
The Whitlock

Find out more about Windsor

Windsor Cottages information

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Frequently asked questions

How much do cottages in Windsor cost?
Cottages in Windsor range between and 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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