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Compare Guest Houses in Pittsfield with updated reviews, rates, and availability.

The Trailside Inn

3.0 star property
9.0 out of 10, Wonderful, (128)
"The owners are great! This hotel is a couple-run property that has a great homemade breakfast and very fulfilling game room."
The price is SAR 620
SAR 682 total
includes taxes & fees
18 Mar - 19 Mar
The Trailside Inn

Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts

9.4 out of 10, Exceptional, (33)
"Overall a great place in a beautiful area next to a skii hill. There were issues with bugs throughout the place when we first arrived. Its important to note there is no mobile service within a mile of this place so make sure to have your wifi and checkin details available. Some parts of the room were dusty and had cobwebs but the owner did have plenty of towels and supplies to make our stay great."
Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts

The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views!

10.0 out of 10, Exceptional, (1)
"Our group had a wonderful stay. The ski out location is great and worked well even for our beginning skiers. The amenities were as described and the views are amazing. The property owner was extremely responsive when a minor issue arose. We highly recommend!"
The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views!

Serene dog-friendly guest house with mountain views, fireplace, & firepit

9.2 out of 10, Wonderful, (12)
"More glasses, wine glasses in particular. Better towels. Figure out TV. I used my streaming credentials, if that is what’s expected pls state that. Bedroom TV I could not figure out and did not use."
Serene dog-friendly guest house with mountain views, fireplace, & firepit

110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool

8.0 out of 10, Very Good, (5)
"Beds not terrible. Sofa bed very terrible. Great pool. Reasanable price vs quality. Renovated in pass years. Clean place"
The price is SAR 453
SAR 665 total
includes taxes & fees
18 Mar - 19 Mar
110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool

Salt Ash Inn

3.0 star property
6.0 out of 10, (126)
"Great place, close proximity to Killington. Clean & quiet...Recommend this location."
Salt Ash Inn
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

Mountain Green

2.0 star property
6.4 out of 10, (7)
"We love the place very much. Clean and cozy, efficient communication. A home away from home, that we call the place we stayed. We would be happy to be back again. "
The price is SAR 700
SAR 940 total
includes taxes & fees
10 Mar - 11 Mar
Mountain Green

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (231)
"Lovely little cabin. Well built, well stocked, comfortable bed and great hot tub! Our host Jeff was helpful and all was well organized for a comfortable peaceful stay. Beautiful surroundings, set among trees and mountains."
Cozy Loft for two with Hot Tub & Mtn Views

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

10.0 out of 10, Exceptional, (483)
"We had a great time at the cabin, our second year!! We plan to be back for a third season!!Everything was perfect, the coziness of the cabin was amazing. We were able to watch the Super Bowl again on the huge projection screen!! Hot tub was great after several long days of skiing and snowshoeing!!"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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.