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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Pittsfield cabin rentals

Exterior detail

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)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is AED 820
AED 1,827 total
includes taxes & fees
6 Aug - 7 Aug
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior detail

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, (16 reviews)
"This was a dash away and perfect! "
United States
Linda R.
The price is AED 459
AED 673 total
includes taxes & fees
7 Aug - 8 Aug
Taborton Harvest Boulder Pines Cabin in the woods
Exterior

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 AED 514
AED 734 total
includes taxes & fees
6 Aug - 7 Aug
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Exterior

4. Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
10.0 out of 10, Exceptional, (2 reviews)
"It was a great getaway "
United States
Chandra F.
The price is AED 459
AED 673 total
includes taxes & fees
6 Aug - 7 Aug
Taborton Harvest Timber Trails Unique cabin experience
Exterior

5. 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 AED 1,068
AED 2,017 total
includes taxes & fees
10 Aug - 11 Aug
Luxury, modern AIRSTREAM at June Farms!
Exterior

6. Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is AED 1,469
AED 2,199 total
includes taxes & fees
10 Aug - 11 Aug
Bear Creek Cabin
Exterior

7. 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 AED 1,464
AED 2,673 total
includes taxes & fees
6 Aug - 7 Aug
A stunning, modern Lodge with rustic charm at June Farms!
Exterior

8. 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 AED 2,838
AED 4,879 total
includes taxes & fees
6 Aug - 7 Aug
A spectacularly charming LAKE HOUSE on gorgeous Burden Lake!
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Escaped into another world on each floor's hallway-the memorabilia and artwork spoke of an honest, New England history. The atmosphere was perfect for a genuine, original immersion into New England's past and LOVED going up and down the 150yr old elevator! Meals delicious w/excellent service. Only one issue we had: the AC in the room was difficult to adjust and were quite chilled even w/turning the thermostat up to 80 deg!!!!!!!!! as suggested by the front desk. Shall make this a yearly visit!"
judy 1-night trip
Posted 7 hours ago
The Red Lion Inn

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