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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Windsor cottages

Interior

12-acre Vacation Rental in the Berkshires!

12-acre Vacation Rental in the Berkshires!
3.0 star property
Charlemont
The price is P14,594
P32,704 total
includes taxes & fees
Apr 19 - Apr 20
12-acre Vacation Rental in the Berkshires!
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
The price is P11,759
P33,215 total
includes taxes & fees
Apr 22 - Apr 23
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

6/10 Okay
"While this is a good value for the money for a one bedroom with separate kitchenette and living area, this is basically 2nd or 3rd rate for a timeshare unit. Couch is uncomfortable to sit on and bed isn't the best. Didn't provide some very basics, such as dish soap to wash dishes and pans which are provided (luckily, we brought our own)."
Nathaniel 3-night trip
Posted 1 hour ago
Vacation Village in the Berkshires

Find out more about Windsor

Windsor Cottages information

Number of reviews
Accommodation
51 Cottages
Lowest Price
P32,704
Highest Price
P33,215

Frequently asked questions

How much do cottages in Windsor cost?
Cottages in Windsor range between P32,704 and P33,215 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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