A lake surrounded by autumn-colored trees and a rocky shoreline.

Search Cabin Rentals in Pittsfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Pittsfield cabin rentals

Exterior

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (43 reviews)
"Very cozy and easy check in!"
United States
Emily R.
The price is AED 463
AED 889 total
includes taxes & fees
5 Jul - 6 Jul
Secluded retreat in the trees
Exterior

Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (168 reviews)
"Jill was very attentive to make sure we had everything we needed very nice stay!"
United States
Kathy B.
The price is AED 793
AED 1,608 total
includes taxes & fees
13 Jul - 14 Jul
Stetson Hollow Cabin by Stetson Brook
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!
Sharon
10.0 out of 10, Exceptional, (12 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is AED 643
AED 1,288 total
includes taxes & fees
30 Jul - 31 Jul
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Exterior

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Cannon was cozy, clean, and as described. "
United States
Addams S.
The price is AED 509
AED 1,734 total
includes taxes & fees
7 Jul - 8 Jul
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Exterior

Brookside Cabin - Your Vermont Offgrid Escape

Brookside Cabin - Your Vermont Offgrid Escape
Brookfield
The price is AED 430
AED 1,358 total
includes taxes & fees
7 Jul - 8 Jul
Brookside Cabin - Your Vermont Offgrid Escape
Exterior

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 1,107
AED 1,496 total
includes taxes & fees
15 Jul - 16 Jul
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
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
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"The host was easy to communicate with, gracious and helpful. Amenities were generous and everything was in excellent condition. Really enjoyed the quiet treed setting and the hot tub."
United States
Elizabeth N.
The price is AED 625
AED 1,506 total
includes taxes & fees
8 Jul - 9 Jul
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Exterior

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 1,107
AED 1,496 total
includes taxes & fees
20 Jul - 21 Jul
Adorable cabin with screened porch and private fire pit
Exterior

Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway

Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway
Mendon
The price is AED 735
AED 1,765 total
includes taxes & fees
5 Jul - 6 Jul
Rustic Mountain Retreat Just Minutes to Pico & Killington for a Perfect Getaway
Cabin 6 (Pet Free) - Evening Star | Pillowtop beds, individually decorated, individually furnished

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (41 reviews)
"Very nice place great owner"
United States
Joe
The price is AED 1,074
AED 1,171 total
includes taxes & fees
7 Jul - 8 Jul
Robert Frost Mountain Cabins
Exterior

Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.

Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.
Killington
9.6 out of 10, Exceptional, (21 reviews)
"Cozy, classic, basic, old school Killington condo. Loved the wood stove. Easy access to Killington area. "
United States
Leslie P.
Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.
Exterior

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

Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Killington
9.8 out of 10, Exceptional, (65 reviews)
"Amazing location, cozy cabin with plenty of beds for sleeping , owners were super responsive will def love to stay again!"
United States
Robert D.
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Exterior

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 1,107
AED 1,492 total
includes taxes & fees
10 Jul - 11 Jul
Cozy and pristine timberframe cabin
Exterior

Charming TREEHOUSE in remote location

Charming TREEHOUSE in remote location
Braintree
10.0 out of 10, Exceptional, (1 review)
The price is AED 1,279
AED 1,708 total
includes taxes & fees
5 Jul - 6 Jul
Charming TREEHOUSE in remote location
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
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 1,107
AED 1,492 total
includes taxes & fees
19 Jul - 20 Jul
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
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!
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Location near gondola was clutch (short 1 min drive). Super clean and layout of cabin was perfect for our group. We had a fair amount of snow and icy weather and our host kept the road and driveway clear."
United States
Jeremy F.
The price is AED 2,204
AED 3,914 total
includes taxes & fees
22 Jul - 23 Jul
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Exterior detail

Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit

Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit
Killington
2.0 out of 10, (1 review)
Roaring Bear Cabin: Secluded Killington Retreat with Hot Tub and Fire Pit
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
Ripton
10.0 out of 10, Exceptional, (12 reviews)
"Excellent facilities enjoyed staying there very much"
United States
Linda
The price is AED 1,107
AED 1,467 total
includes taxes & fees
30 Jul - 31 Jul
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
Ripton
10.0 out of 10, Exceptional, (7 reviews)
"This is a very special place. Close to Middleburyyetfar away. "
United States
Jim P.
Inviting timber frame cabin in Vermont's Green Mountains
Exterior

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

Cabin at Killington: Large Home w/ amenities, views and location close to ski resort. Hot Tub.
Killington
10.0 out of 10, Exceptional, (18 reviews)
"great stay!"
United States
Patrick M.
Cabin at Killington: Large Home w/ amenities, views and location close to ski resort. Hot Tub.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

The Jackson

The Jackson

10/10 Excellent
"My only complaint is that our television didn't work. And we told the staff member setting up the evening wine and cheese that and she said someone else had also had the problem. We had had a thunderstorm and thought that maybe that was it, and she said she would check in our room while we were gone that evening. But when we returned, the television still didn't work and there was no indication that anybody."
Martha 1-night trip
Posted 1 hour ago
The Jackson

Explore a world of travel with Expedia