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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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
$497 nightly
The price is $555
Nov 8 - Nov 9
Total with taxes and fees
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
$499 nightly
The price is $554
Oct 18 - Oct 19
Total with taxes and fees
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)
$1,809 nightly
The price is $1,836
Oct 18 - Oct 19
Total with taxes and fees
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

10/10 Excellent
"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"
Hope 1-night trip
Posted 6 hours ago
The Red Lion Inn

Find out more about Windsor

Windsor Cottages information

Number of reviews
Accommodation
67 Cottages
Lowest Price
$554
Highest Price
$1,836

Frequently asked questions

How much do cottages in Windsor cost?
Cottages in Windsor range between $554 and $1,836 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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