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Compare 33 Cottages in Windsor with updated reviews, rates, and availability.

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

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

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

Berkshire Hideaway w/ Fire Pit & Playground!

3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!

Historic Huntington Home - Walk to Westfield River

3.0 star property
Historic Huntington Home - Walk to Westfield River

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

Becket Home w/ 3-season Porch: Walk to Lake Access

3.0 star property
Becket Home w/ 3-season Porch: Walk to Lake Access

Cozy Southern Vermont Home w/ On-site Trails

3.0 star property
Cozy Southern Vermont Home w/ On-site Trails

Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!

3.0 star property
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3.0 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!

Walk to Dining: Downtown Lenox Guest House!

3.0 star property
Walk to Dining: Downtown Lenox Guest House!

Elegant Pittsfield Home Near Downtown & Skiing!

3.0 star property
Elegant Pittsfield Home Near Downtown & Skiing!

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

3.0 star property
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

Berkshires Cabin 2 Mi to Appalachian Trail!

3.0 star property
Berkshires Cabin 2 Mi to Appalachian Trail!
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

3.0 star property
8.6 out of 10, Excellent, (1804)
"It was off season and quiet. Great price :)"
The price is NT$3,315
NT$4,034 total
includes taxes & fees
May 12 - May 13
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (929)
"Last minute find. Room was tidy/no odors. The kitchen was complete and cute wood art made the place feel cozy. The spare roll away bed was delivered as requested, and surprisingly comfortable. Traveled with hubby and 9 year old between seasons to hit Bash Bish. Will stay here again to visit Naumkeag."
The price is NT$4,054
NT$4,528 total
includes taxes & fees
May 12 - May 13
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.