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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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
$499 nightly
The price is $554
Sep 6 - Sep 7
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

2. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
$2,274 nightly
The price is $2,305
Sep 14 - Sep 15
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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Hotel was clean and stag was helpful and friendly."
Basil 2-night trip
Posted 17 hours ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Windsor

Windsor Cottages information

Number of reviews
Accommodation
70 Cottages
Lowest Price
$554
Highest Price
$554

Frequently asked questions

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