A historic building with classical architecture, a traffic light, and a yellow taxi.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Pittsfield cabin rentals

A white building with a window, surrounded by trees and forest.

1. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (39 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is SAR 848
SAR 1,874 total
includes taxes & fees
5 Oct - 6 Oct
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A wooden cabin with a white door, a small porch, and a sign reading "Boulder Pines."

2. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (18 reviews)
"This was a dash away and perfect! "
United States
Linda R.
The price is SAR 469
SAR 688 total
includes taxes & fees
3 Oct - 4 Oct
Taborton Harvest Boulder Pines Cabin in the woods
A small wooden cabin with a pitched roof, a front door, and a porch.

3. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is SAR 526
SAR 754 total
includes taxes & fees
4 Oct - 5 Oct
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
A wooden cabin with a porch and multiple windows.

4. Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
10.0 out of 10, Exceptional, (4 reviews)
"It was a great getaway "
United States
Chandra F.
The price is SAR 469
SAR 688 total
includes taxes & fees
4 Oct - 5 Oct
Taborton Harvest Timber Trails Unique cabin experience
A red cabin with a screened porch, a small deck, and a barbecue grill in a wooded area.

5. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is SAR 751
SAR 1,426 total
includes taxes & fees
13 Oct - 14 Oct
Ideal location for summer and winter activities with plenty of outdoor space.
A small, single-story building with a sloped roof and a covered porch.

6. A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!

A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
Averill Park
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful family weekend at the lake house. Beautiful place to stay. Perfect for a family gathering."
United States
KenD
The price is SAR 1,318
SAR 2,980 total
includes taxes & fees
4 Oct - 5 Oct
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
A mobile home with a red awning, surrounded by a forest.

7. Luxury, modern AIRSTREAM at June Farms!

Luxury, modern AIRSTREAM at June Farms!
West Sand Lake
9.8 out of 10, Exceptional, (7 reviews)
"We’ve stayed at several of the various cabins at June Farms. This one, like the others, is unique and fantastic. Would absolutely stay again!"
United States
StephenS
The price is SAR 1,092
SAR 2,062 total
includes taxes & fees
6 Oct - 7 Oct
Luxury, modern AIRSTREAM at June Farms!
A log cabin with large windows and a wooden deck.

8. Bear Creek Cabin

Bear Creek Cabin
Charlemont
9.8 out of 10, Exceptional, (54 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is SAR 1,502
SAR 2,248 total
includes taxes & fees
5 Oct - 6 Oct
Bear Creek Cabin
A wooden cabin with a porch, surrounded by lush greenery and trees.

9. A stunning, modern Lodge with rustic charm at June Farms!

A stunning, modern Lodge with rustic charm at June Farms!
West Sand Lake
10.0 out of 10, Exceptional, (5 reviews)
"2nd time staying at The Lodge , had a wonderful relaxing few days ! Enjoyed long walks , and the animals . The weather was perfect , couldn't have asked for anything more! Thank you !"
United States
LisaL
The price is SAR 1,663
SAR 2,938 total
includes taxes & fees
6 Oct - 7 Oct
A stunning, modern Lodge with rustic charm at June Farms!
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

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"My impression s? It’s a quiet rural area, but I am impressed how quiet the motel was. Not all the time, but occasionally it get noisy. I also liked the area."
Casey A 4-night trip
Posted 8 hours ago
Best Western Plus Berkshire Hills Inn & Suites