Search Windsor Cottages

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In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Windsor cottages

House (3 Bedrooms) | Interior

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
Apr 5 - Apr 6
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (1 review)
"This place is simply fantastic. If you are looking for quiet...and I mean ABSOLUTE quiet...this is your place! Nestled just five minutes south of Readsboro, VT, Brookside Cottage is the place to get disconnected and just breathe a bit. Our family needed this place...I needed to be here...with our kids growing up so fast, now at 14 and 11, my wife and I just wanted to have a few days to be together, play some games, watch some movies, and enjoy each other's company. I'm convinced we found the...
United States
Jason H.
$263 nightly
The price is $295
Apr 7 - Apr 8
Total with taxes and fees
Brookside cottage near the mountains and outdoor recreation
Interior

12-acre Vacation Rental in the Berkshires!

12-acre Vacation Rental in the Berkshires!
3.0 star property
Charlemont
$515 nightly
The price is $545
Apr 5 - Apr 6
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Beds could be more updated"
seth 2-night trip
Posted 11 hours ago
Vacation Village in the Berkshires

Find out more about Windsor

Windsor Cottages information

Number of reviews
1
Accommodation
74 Cottages
Lowest Price
$295
Highest Price
$554

Frequently asked questions

How much do cottages in Windsor cost?
Cottages in Windsor range between $295 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?
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