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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Pittsfield cabin rentals

Exterior
Secluded retreat in the trees

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful location and property. Hosts were welcoming and we had a comfortable stay. Hannah shared a bunch of local recommendations and tips! We had a great getaway!"
United States
Niti P.
The price is AED 463
AED 864 total
includes taxes & fees
15 Jan - 16 Jan
Secluded retreat in the trees
Exterior
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
Rutland
9.6 out of 10, Exceptional, (7 reviews)
The price is AED 551
AED 708 total
includes taxes & fees
22 Jan - 23 Jan
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Exterior
Robert Frost Mountain Cabins

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
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
20 Jan - 21 Jan
Robert Frost Mountain Cabins
Exterior
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (5 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
The price is AED 551
AED 1,172 total
includes taxes & fees
5 Feb - 6 Feb
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Exterior
Adorable cabin with screened porch and private fire pit

Adorable cabin with screened porch and private fire pit

Adorable cabin with screened porch and private fire pit
Ripton
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 1,269 total
includes taxes & fees
15 Jan - 16 Jan
Adorable cabin with screened porch and private fire pit
Exterior
Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (160 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
15 Jan - 16 Jan
Stetson Hollow Cabin by Stetson Brook
Exterior
Charming TREEHOUSE in remote location

Charming TREEHOUSE in remote location

Charming TREEHOUSE in remote location
2.0 star property
Braintree
The price is AED 800
AED 1,102 total
includes taxes & fees
26 Jan - 27 Jan
Charming TREEHOUSE in remote location
Exterior
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Ripton
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
19 Jan - 20 Jan
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Exterior
Cozy and pristine timberframe cabin

Cozy and pristine timberframe cabin

Cozy and pristine timberframe cabin
Ripton
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 1,269 total
includes taxes & fees
20 Jan - 21 Jan
Cozy and pristine timberframe cabin
Exterior
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Ripton
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 1,269 total
includes taxes & fees
22 Jan - 23 Jan
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Exterior
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Hancock
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 1,055
AED 2,041 total
includes taxes & fees
19 Jan - 20 Jan
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Exterior
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Killington
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 2,204
AED 3,914 total
includes taxes & fees
9 Feb - 10 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

Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Ripton
10.0 out of 10, Exceptional, (12 reviews)
"Excellent facilities enjoyed staying there very much"
United States
Linda
The price is AED 940
AED 1,269 total
includes taxes & fees
28 Jan - 29 Jan
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Exterior
Inviting timber frame cabin in Vermont's Green Mountains

Inviting timber frame cabin in Vermont's Green Mountains

Inviting timber frame cabin in Vermont's Green Mountains
Ripton
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
Exterior
Immaculate mountain cabin with awe inspiring sunrise and mountain views

Immaculate mountain cabin with awe inspiring sunrise and mountain views

Immaculate mountain cabin with awe inspiring sunrise and mountain views
Ripton
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 1,269 total
includes taxes & fees
15 Jan - 16 Jan
Immaculate mountain cabin with awe inspiring sunrise and mountain views
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

North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"Outdoor pool, nice large fireplace. On the Access road. We've stayed many times here over the years. "
William E Cook 3-night trip
Posted 1 day ago
North Star Lodge and Resort