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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Pittsfield cabin rentals

Exterior
Secluded retreat in the trees

Cabin in Roxbury

Secluded retreat in the trees
10.0 out of 10, Exceptional, (39 reviews)
"Idyllic setting, felt like I was home. "
United States
Karen R.
The price is AED 463
AED 864 total
includes taxes & fees
10 Jan - 11 Jan
Secluded retreat in the trees
Exterior
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Cabin in Sharon

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
10.0 out of 10, Exceptional, (5 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
The price is AED 454
AED 1,039 total
includes taxes & fees
13 Jan - 14 Jan
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Exterior
Robert Frost Mountain Cabins

Cabin in Ripton

Robert Frost Mountain Cabins
3.5 star property
10.0 out of 10, Exceptional, (40 reviews)
"Ammazing,would go again!"
United States
Joseph
The price is AED 953
AED 1,039 total
includes taxes & fees
14 Jan - 15 Jan
Robert Frost Mountain Cabins
Exterior
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cabin in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
9.6 out of 10, Exceptional, (7 reviews)
The price is AED 555
AED 712 total
includes taxes & fees
19 Jan - 20 Jan
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Exterior
Adorable cabin with screened porch and private fire pit

Cabin in Ripton

Adorable cabin with screened porch and private fire pit
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful place to stay tucked away in the woods. The owners are extremely thoughtful and personable. Can’t wait to go back. "
United States
Sorin
The price is AED 940
AED 1,265 total
includes taxes & fees
11 Jan - 12 Jan
Adorable cabin with screened porch and private fire pit
Exterior
Stetson Hollow Cabin by Stetson Brook

Cabin in Warren

Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, (159 reviews)
"It’s an authentic cabin in the woods and it was just as I hoped it would be - amazing! The owners Jill and John were very friendly and helpful. "
United States
Tom O.
The price is AED 793
AED 1,604 total
includes taxes & fees
11 Jan - 12 Jan
Stetson Hollow Cabin by Stetson Brook
Exterior
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cabin in Hancock

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
10.0 out of 10, Exceptional, (1 review)
"This place was great, and perfect for our night’s stay. The hot tub was clean and in excellent condition and we loved having that amenity! The owner was easy to get in touch with and replied to my questions very quickly. We’d love to visit again!"
United States
Stephanie F.
The price is AED 592
AED 1,453 total
includes taxes & fees
14 Jan - 15 Jan
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Exterior
Charming TREEHOUSE in remote location

Cabin in Braintree

Charming TREEHOUSE in remote location
2.0 star property
The price is AED 790
AED 1,095 total
includes taxes & fees
12 Jan - 13 Jan
Charming TREEHOUSE in remote location
Exterior
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Cabin in Ripton

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
9.4 out of 10, Exceptional, (12 reviews)
"Our group booked this place for a ski trip to sugarbush. A remote area, but the cabin was very cool and our host were the best. The warm cinnamon twists in the morning were a big hit and the hot tub was perfect after a day of skiing. Would definitely look into booking this in the summer/fall. "
United States
John H.
The price is AED 940
AED 1,273 total
includes taxes & fees
12 Jan - 13 Jan
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Exterior
Cozy and pristine timberframe cabin

Cabin in Ripton

Cozy and pristine timberframe cabin
10.0 out of 10, Exceptional, (4 reviews)
"It is a gorgeous property with lots of fun amenities...perfect for a winter getaway"
United States
Karen H.
The price is AED 940
AED 1,265 total
includes taxes & fees
11 Jan - 12 Jan
Cozy and pristine timberframe cabin
Exterior
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Cabin in Ripton

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful place. Lots to do around the cabin and in the area. The hosts are very helpful. The cabin has everything you could want for a great stay. "
United States
Susan
The price is AED 940
AED 1,273 total
includes taxes & fees
22 Jan - 23 Jan
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Exterior detail
Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit

Cabin in Killington

Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit
2.0 star property
The price is AED 2,032
AED 4,059 total
includes taxes & fees
11 Jan - 12 Jan
Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit
Exterior
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

Cabin in Killington

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
10.0 out of 10, Exceptional, (1 review)
"Overall a great place. Beautiful location, tucked away from everything but still jist a few minutes from Killington base. Very clean and well-kept, everything we needed was there.Host communicated regularly and responded quickly.If you stay in winter, 4WD might be needed to get in and out without issue. And for the shorter route to and from Killington - its a very steep road.Beautiful interior, needs some age to feel warmer and homey, but good seating and open family room is great for...
United States
Jamie M.
The price is AED 4,224
AED 6,475 total
includes taxes & fees
1 Feb - 2 Feb
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Exterior
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

Cabin in Ripton

Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
10.0 out of 10, Exceptional, (12 reviews)
"Excellent facilities enjoyed staying there very much"
United States
Linda
The price is AED 940
AED 1,273 total
includes taxes & fees
13 Jan - 14 Jan
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Exterior
Immaculate mountain cabin with awe inspiring sunrise and mountain views

Cabin in Ripton

Immaculate mountain cabin with awe inspiring sunrise and mountain views
10.0 out of 10, Exceptional, (3 reviews)
"Our cabin was lovely—artfully built, well-stocked, perfectly clean, and very comfortable. We awoke to silence and a beautiful view of the mountains from our screened porch. We are already planning our return!"
United States
Sara S.
The price is AED 940
AED 1,273 total
includes taxes & fees
11 Jan - 12 Jan
Immaculate mountain cabin with awe inspiring sunrise and mountain views
Exterior
Inviting timber frame cabin in Vermont's Green Mountains

Cabin in Ripton

Inviting timber frame cabin in Vermont's Green Mountains
10.0 out of 10, Exceptional, (6 reviews)
"This is a very special place. Close to Middleburyyetfar away. "
United States
Jim P.
The price is AED 940
AED 1,273 total
includes taxes & fees
19 Jan - 20 Jan
Inviting timber frame cabin in Vermont's Green Mountains
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 Pittsfield Hotel Reviews

Greenbrier Inn

Greenbrier Inn

10/10 Excellent
"Excellent staff extremely clean and comfortable. Highly recommend a stay here to ski at Killington. A ten minute ride to the mountain. "
Richard 1-night trip
Posted 2 days ago
Greenbrier Inn