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Compare 6 Guest Houses in Pittsfield with updated reviews, rates, and availability.
![Room](https://images.trvl-media.com/lodging/9000000/8380000/8370400/8370321/5bc466dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
The Trailside Inn
The Trailside Inn
9.0 out of 10, Wonderful, (126)
The price is AED 607
AED 667 total
includes taxes & fees
23 Feb - 24 Feb
![](https://images.trvl-media.com/lodging/88000000/87590000/87589900/87589843/42bd270f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts
Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts
9.4 out of 10, Exceptional, (33)
![](https://images.trvl-media.com/lodging/112000000/111750000/111740100/111740098/a6c98ee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views!
The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views!
10.0 out of 10, Exceptional, (1)
![](https://images.trvl-media.com/lodging/96000000/95850000/95847700/95847652/40a63d91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Serene dog-friendly guest house with mountain views, fireplace, & firepit
Serene dog-friendly guest house with mountain views, fireplace, & firepit
9.2 out of 10, Wonderful, (12)
![Relax in the living area with a pull out sofa, dinette, TV, and sliding glass doors leading to the padio.](https://images.trvl-media.com/lodging/39000000/38420000/38412900/38412831/w1999h1332x1y1-d679dde8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool
110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool
8.0 out of 10, Very Good, (5)
The price is AED 444
AED 652 total
includes taxes & fees
16 Mar - 17 Mar
![Front of property](https://images.trvl-media.com/lodging/2000000/1790000/1787800/1787707/bedd09a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Salt Ash Inn
Salt Ash Inn
6.0 out of 10, (126)
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
!["This cute and cozy loft was perfect in every way!" JV](https://images.trvl-media.com/lodging/60000000/59790000/59784500/59784421/434c8b92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Cozy Loft for two with Hot Tub
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (230)
![Front of property](https://images.trvl-media.com/lodging/22000000/21440000/21432600/21432554/e989f724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
9.0 out of 10, Wonderful, (41)
![](https://images.trvl-media.com/lodging/34000000/33140000/33137800/33137739/660fbfbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
9.0 out of 10, Wonderful, (43)
The price is AED 349
AED 664 total
includes taxes & fees
18 Feb - 19 Feb
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.
Recent reviews of Pittsfield hotels
Recent reviews of Pittsfield hotels
![My Place Hotel-Randolph VT](http://images.trvl-media.com/lodging/106000000/105670000/105665800/105665795/6629084b_y.jpg)
My Place Hotel-Randolph VT
5/5 Excellent
"."
A verified traveler from dedham stayed at My Place Hotel-Randolph VT
Posted 1 day ago
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