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Featured Cottages in Windsor

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Interior
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Spacious Historic Home in the Berkshires!
Interior
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
2 bedrooms, iron/ironing board, bed sheets
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Charlemont Retreat on Chickley River w/ EV Charger
Interior
Charlemont Retreat on Chickley River w/ EV Charger
3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Stockbridge Home: Walk to Town Beach!
Private kitchen
Stockbridge Home: Walk to Town Beach!
3.0 star property
Stockbridge Home: Walk to Town Beach!
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Interior
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Peaceful Family Home w/ Fire Pit & Large Yard
Interior
Peaceful Family Home w/ Fire Pit & Large Yard
3.0 star property
Peaceful Family Home w/ Fire Pit & Large Yard
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Interior
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Berkshire Hideaway w/ Fire Pit & Playground!
Interior
Berkshire Hideaway w/ Fire Pit & Playground!
3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
3.0 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Berkshires Cabin 2 Mi to Appalachian Trail!
Interior
Berkshires Cabin 2 Mi to Appalachian Trail!
3.0 star property
Berkshires Cabin 2 Mi to Appalachian Trail!
Historic Huntington Home - Walk to Westfield River
Private kitchen
Historic Huntington Home - Walk to Westfield River
3.0 star property
Historic Huntington Home - Walk to Westfield River
Lakeside Berkshires Home Near Hiking & Skiing!
Interior
Lakeside Berkshires Home Near Hiking & Skiing!
3.0 star property
Lakeside Berkshires Home Near Hiking & Skiing!
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
Interior
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
3.0 star property
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
Cozy Southern Vermont Home w/ On-site Trails
Private kitchen
Cozy Southern Vermont Home w/ On-site Trails
3.0 star property
Cozy Southern Vermont Home w/ On-site Trails
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Interior
Cozy Stockbridge Cabin - Walk to Beach & Lake!
3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Historic New Lebanon Hideaway on 33 Private Acres!
Interior
Historic New Lebanon Hideaway on 33 Private Acres!
3.0 star property
Historic New Lebanon Hideaway on 33 Private Acres!
Elegant Pittsfield Home Near Downtown & Skiing!
Property grounds
Elegant Pittsfield Home Near Downtown & Skiing!
3.0 star property
Elegant Pittsfield Home Near Downtown & Skiing!
Picturesque Cottage With Sunroom on Ashmere Lake!
Interior
Picturesque Cottage With Sunroom on Ashmere Lake!
3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
Luxury Vacation Rental in the Berkshires!
TV, books
Luxury Vacation Rental in the Berkshires!
3.0 star property
Luxury Vacation Rental in the Berkshires!
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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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Other property types in Windsor

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1715)
"Always love this place. "
The price is S$250
includes taxes & fees
29 Sept - 30 Sept
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (898)
"Was good everything "
The price is S$209
includes taxes & fees
14 Oct - 15 Oct
Jiminy Peak Mountain Resort
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.

Frequently asked questions

How much do cottages in Windsor cost?
Cottages in Windsor range between and per night. These properties offer a chance to touch base with nature — 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?
We think that vacays should be a piece of cake, so if you’re on the lookout for cottages in Windsor at a great price, Expedia has your back. Keep the budget in check and pick an economical option far away from the city rush, or book an upscale cottage to treat your loved ones.
How can I find cheap cottages in Windsor?
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