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In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Our top choices for Windsor cottages

House (3 Bedrooms) | Interior

Cottage in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
$499 nightly
The price is $554
Mar 21 - Mar 22
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Cottage in New Lebanon

Berkshires farm, 30+ guests, 50 acres
10.0 out of 10, Exceptional, (1 review)
$1,742 nightly
The price is $1,766
Mar 23 - Mar 24
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres
Interior

Cottage in Charlemont

12-acre Vacation Rental in the Berkshires!
3.0 star property
$515 nightly
The price is $545
Mar 21 - Mar 22
Total with taxes and fees
12-acre Vacation Rental in the Berkshires!
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 Williams Inn

The Williams Inn

10/10 Excellent
"one of my favorite places to stay..."
Augusta 1-night trip
Posted 21 hours ago
The Williams Inn

Find out more about Windsor

Windsor Cottages information

Number of reviews
Accommodation
74 Cottages
Lowest Price
$554
Highest Price
$1,766

Frequently asked questions

How much do cottages in Windsor cost?
Cottages in Windsor range between $554 and $1,766 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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