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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Cabin Rentals in Windsor

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (224)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Florida Mountain Log Cabin!
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Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
The price is AED 781
AED 1,559 total
includes taxes & fees
23 Oct - 24 Oct
Florida Mountain Log Cabin!
The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly
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The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly

10.0 out of 10, Exceptional, (3)
"Wonderful view, peaceful quiet area, cosy cabin."
The price is AED 866
AED 1,676 total
includes taxes & fees
6 Oct - 7 Oct
The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly
Bear Creek Cabin
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Bear Creek Cabin

9.8 out of 10, Exceptional, (39)
"We enjoyed our stay!!"
The price is AED 1,469
AED 2,154 total
includes taxes & fees
4 Oct - 5 Oct
Bear Creek Cabin
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
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Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.

9.6 out of 10, Exceptional, (62)
"Great"
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
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Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

9.8 out of 10, Exceptional, (30)
"Hindsale-perfect little hideaway, minutes from where we needed to be. Harrison’s little home was equipped with amenities/tasteful luxuries, and cozy nooks. We all loved the loft-could not believe how large the space was! Hot tub nights-perfect ending:) Thank you, Harrison."
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
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A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (128)
"5 stars all around very relaxing and a great location. John is a great host too very accommodating!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Berkshire Mountain Cottage - Spectacular Views of Mount Greylock
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Berkshire Mountain Cottage - Spectacular Views of Mount Greylock

Berkshire Mountain Cottage - Spectacular Views of Mount Greylock
Lakefront House with Stunning Views and Great Room
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Lakefront House with Stunning Views and Great Room

9.8 out of 10, Exceptional, (19)
"Beautiful setting. We had fun exploring the area and made good use of the kayaks to explore the lake."
Lakefront House with Stunning Views and Great Room
Artist's Camp on Lake Mahkeenac
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Artist's Camp on Lake Mahkeenac

9.6 out of 10, Exceptional, (19)
"Great location, comfortable, beautiful setting and nice porch! "
Artist's Camp on Lake Mahkeenac
Dadzpad Cabin in Stephentown
Property grounds

Dadzpad Cabin in Stephentown

5.0 out of 10, (2)
"House was clean and comfortably furnished. The kids enjoyed the arcade games and it was an overall good time. Only Issues were that the drive and walk ways were hidden in the snow and the house did not hold heat well "
Dadzpad Cabin in Stephentown
Charming 3-bedroom Cabin for nature lovers
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Charming 3-bedroom Cabin for nature lovers

8.0 out of 10, Very Good, (1)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
The price is AED 484
AED 1,067 total
includes taxes & fees
29 Sep - 30 Sep
Charming 3-bedroom Cabin for nature lovers
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
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Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum

9.8 out of 10, Exceptional, (57)
"Great cabin on a beautiful lake. Scenic drive to all other attractions in the Berkshires (Lenox, Mt. Greylock, etc.). We enjoyed our stay!"
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Vermont Lake Front Log Cabin Close to Mt. Snow
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Vermont Lake Front Log Cabin Close to Mt. Snow

10.0 out of 10, Exceptional, (69)
"The property was very nice, and the host was very accommodating and responsive. Would definitely stay here again. "
Vermont Lake Front Log Cabin Close to Mt. Snow
A post and beam home in a private setting with wonderful mountain views.
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A post and beam home in a private setting with wonderful mountain views.

9.8 out of 10, Exceptional, (118)
"Clean, very confortable and with everything needed to relax and have a great time. The property has ample space, we had a great time and felt nature in all it's splendor. Definitely recommended."
A post and beam home in a private setting with wonderful mountain views.
Lakeshore cabin with beach and dock
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Lakeshore cabin with beach and dock

10.0 out of 10, Exceptional, (4)
"Took advantage of the peaceful setting and location to nearby attractions!"
Lakeshore cabin with beach and dock
Berkshires Cabin steps from Lake
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Berkshires Cabin steps from Lake

9.6 out of 10, Exceptional, (4)
"For a winter visit, the A-frame and cedar panelling were welcoming and cozy. The 3-season room in the back would be great for a warm weather visit. Host was accessible and responsive by text. A really nice stay."
Berkshires Cabin steps from Lake
Cozy cabin in tranquil Canaan NY with WiFi, AC
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Cozy cabin in tranquil Canaan NY with WiFi, AC

Cozy cabin in tranquil Canaan NY with WiFi, AC
Cozy Modern 4 Bedroom Log Cabin on 45 Secluded Acres in the Berkshires
Property grounds

Cozy Modern 4 Bedroom Log Cabin on 45 Secluded Acres in the Berkshires

Cozy Modern 4 Bedroom Log Cabin on 45 Secluded Acres in the Berkshires
Cozy 2-bedroom cabin in charming Becket with WiFi, AC
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Cozy 2-bedroom cabin in charming Becket with WiFi, AC

Cozy 2-bedroom cabin in charming Becket with WiFi, AC
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

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Staff is friendly and accommodating "
Karol 1-night trip
Posted 3 days ago
Best Western Plus Berkshire Hills Inn & Suites