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

Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (95)
"A great place in a great location with super-responsive and helpful owners! My partner is a teacher and she was entranced with the schoolroom, the history, and the old textbooks!"
Charming historic cottage on scenic road to Mt. Greylock
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
"the property was very well maintain, the host put alot of very personal and special touches inside the house.i have stayed in alot of houses over the years, but this one the host made you feel right at home."
Cozy Berkshire cottage with fireplace.
Cozy Berkshires Cottage w/ 11 Private Acres!
Cozy Berkshires Cottage w/ 11 Private Acres!
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Beachwood Cottage
10.0 out of 10, Exceptional, (1)
"Second time staying at the property. Comfortable, low key cabin. Access to private beach a big plus. Near Lenox, Stockbridge and Tanglewood."
The price is AED 1,010
AED 1,986 total
includes taxes & fees
8 Jul - 9 Jul
Beachwood Cottage
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!
3.5 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Charlemont Retreat on Chickley River w/ EV Charger
3.5 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
Cottage in the Clouds With Mountain Views
10.0 out of 10, Exceptional, (1)
"A sanctuary for writers and astronomers! Exquisite cottage and surroundings. Short hop to all that goes on in the Berkshires. You won't want to leave!"
Cottage in the Clouds With Mountain Views
Picturesque Cottage with Sunroom on Ashmere Lake!
9.6 out of 10, Exceptional, (17)
"It was perfect for me and my close friends. We enjoyed the lake each day and all remarked that the beds were very comfortable. Wish we could have stayed longer."
Picturesque Cottage with Sunroom on Ashmere Lake!
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Private Lake Cottage on 3 acres w/350 sq. ft. deck
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
3.5 star property
Peaceful Family Home w/ Fire Pit & Large Yard
Black Bear Mountain Cottage
Black Bear Mountain Cottage
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
3.5 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Berkshires Cabin 2 Mi to Appalachian Trail!
3.0 star property
Berkshires Cabin 2 Mi to Appalachian Trail!
Stockbridge Home: Walk to Town Beach!
3.5 star property
Stockbridge Home: Walk to Town Beach!
Historic Huntington Home - Walk to Westfield River
3.5 star property
Historic Huntington Home - Walk to Westfield River
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!
3.5 star property
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux
Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux
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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.

Other property types in Windsor

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (860)
"This is a sweet property. I visited in the summer. The dining options were great. The country store is awesome. I love how the rooms are suites. They feel like small apartments. I like that they have kitchens. The bed was comfortable. The ac is loud but at least it works well and it drowns out other noises. I needed a late check out and they were very cool about it. They let me hang out at the pool and then shower at the spa because I was like of stuck there several hours after check out time....
The price is AED 584
AED 641 total
includes taxes & fees
23 Jun - 24 Jun
Jiminy Peak Mountain Resort
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (8)
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Pristine Home In Becket Woods
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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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