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Compare 79 Cabin Rentals in Pittsfield with updated reviews, rates, and availability.

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (492)
"We had an amazing time at his wonderful property. The hiking trails were close and the hot tub was a nice treat after our adventures. The cabin was well equipped and we didn't need a thing. Thank you!"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (237)
"Wonderful place "
Cozy Loft for two with Hot Tub & Mtn Views

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (206)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Charming farmhouse, dog friendly, Appalachian trail access

7.2 out of 10, Good, (5)
"A lovely "get-away" in beautiful Vermont."
Charming farmhouse, dog friendly, Appalachian trail access

Stetson Hollow Cabin by Stetson Brook

9.8 out of 10, Exceptional, (145)
"Cozy warm log cabin with a beautiful fireplace and excellent, accommodating hosts. Perfect spot for a getaway weekend in VT."
The price is AED 882
AED 1,711 total
includes taxes & fees
4 May - 5 May
Stetson Hollow Cabin by Stetson Brook

Secluded retreat in the trees

10.0 out of 10, Exceptional, (18)
"Quiet, comfy, large windows looking out on autumn foliage. Perfect for our central Vermont adventures."
Secluded retreat in the trees

Classic Vermont Cabin on 2.5 acres Lake Frontage

9.8 out of 10, Exceptional, (105)
"We had a very nice stay and enjoyed our time at Lake Dunmore."
Classic Vermont Cabin on 2.5 acres Lake Frontage

Pond View Cabin-Rustic 2 Bedroom-Sleeps 4

9.0 out of 10, Wonderful, (2)
"easy checkin / out. short drive to Killington. "
Pond View Cabin-Rustic 2 Bedroom-Sleeps 4

Killington / Mendon CLEAN, 2 bedroom cabin

9.8 out of 10, Exceptional, (6)
"Exactly as advertised, clean and good location. Friendly owners."
Killington / Mendon CLEAN, 2 bedroom cabin

Robert Frost Mountain Cabins

3.5 star property
10.0 out of 10, Exceptional, (40)
"We loved how cozy and warm the cabin was, how easy the fireplace was to operate, and how much room we had. The view of sunrise from the back window and our ability to walk out there to enjoy it was a pleasant surprise. We'd love to come back."
The price is AED 992
AED 1,081 total
includes taxes & fees
9 May - 10 May
Robert Frost Mountain Cabins

Killington Area Escape w/ Deck, Views & Hot Tub!

9.6 out of 10, Exceptional, (19)
"Was perfect. Property owner very prompt on responses. Definitely reccomend !"
Killington Area Escape w/ Deck, Views & Hot Tub!

Killington / Mendon CLEAN, 2 bedroom cabin

10.0 out of 10, Exceptional, (7)
"Stayed here with my three children while skiing at Killington Mountain. It was a really nice cabin with a little fireplace which made it cozy even when it was really cold outside. The owner was very nice, and made sure we had a great stay. Highly recommend this property for other ski lovers, it's super close to PICO and not far from Killington, took 10 mins to drive to Ramshead. Beautiful area. "
Killington / Mendon CLEAN, 2 bedroom cabin

Killington / Mendon CLEAN, 1 bedroom cabin

10.0 out of 10, Exceptional, (18)
"Clean and close to the mountain"
Killington / Mendon CLEAN, 1 bedroom cabin

The Cabin that brings people together

9.6 out of 10, Exceptional, (79)
"Had a blast staying in this beautiful cabin. Missed the teepee but couldn't have asked for a better stay!"
The Cabin that brings people together

Cozy private cabin, wood stove, w/d, TVs, wifi, deck, close to skiing & golfing

10.0 out of 10, Exceptional, (1)
"Great house, wonderful time!"
Cozy private cabin, wood stove, w/d, TVs, wifi, deck, close to skiing & golfing

Cabin at Killington: Large Home w/ amenities, views and location close to ski resort. Hot Tub.

10.0 out of 10, Exceptional, (13)
"We needed a large house to accommodate 20 golfers at Killing and Green Mountain National. The house is a little aged, but clean and perfect for what we were looking for. Had a few questions and the owner was very responsive, check in was easy and location was perfect."
The price is AED 1,915
AED 4,410 total
includes taxes & fees
5 May - 6 May
Cabin at Killington: Large Home w/ amenities, views and location close to ski resort. Hot Tub.

Picture-Perfect Vermont Mtn Cabin w/ Hot Tub!

9.8 out of 10, Exceptional, (16)
"It was perfect for our family of 12. Close to skiing, Woodstock, Beautiful countryside around our house. "
Picture-Perfect Vermont Mtn Cabin w/ Hot Tub!

Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape

10.0 out of 10, Exceptional, (62)
"The cabin was lovely and we really enjoyed staying there. Proximity to the mountain and everything in town was great. "
The price is AED 642
AED 1,866 total
includes taxes & fees
4 May - 5 May
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape

The Pond Cabin at Sky Hollow, The Hunter Cabin at Sky Hollow

10.0 out of 10, Exceptional, (1)
"Perfect size little cabin that was warm and dry, a perfect refuge after a week of camping! Lovely property with everything we needed, and we loved seeing the baby cows every morning. Location was great and close to many trails in the national forest. "
The Pond Cabin at Sky Hollow, The Hunter Cabin at Sky Hollow
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 Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 13+

9.8 out of 10, Exceptional, (117)
"Had a great stay in the perfect ski house "
Killington area home - 4-seasons & hot tub. Sleeps 13+

Private Killington Area Inn all to Yourself!

10.0 out of 10, Exceptional, (38)
"Overall fabulous place to stay. Will be back next year!!"
Private Killington Area Inn all to Yourself!

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern 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.