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Compare 6 Guest Houses in Pittsfield with updated reviews, rates, and availability.

The Trailside Inn

3.0 star property
9.0 out of 10, Wonderful, (130)
"Such a great, comfortable place to stay with an awesome staff!"
The Trailside Inn

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

10.0 out of 10, Exceptional, (2)
"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 price is SAR 1,448
SAR 3,295 total
includes taxes & fees
25 Apr - 26 Apr
The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views!

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

9.4 out of 10, Exceptional, (33)
"This was such a peaceful and beautiful place to stay! Everything was perfectly clean and organized. We would definitely stay there again. Wish we could've stayed longer!"
Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts

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

8.8 out of 10, Excellent, (13)
"Relaxing after a days hike."
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)
"The view of the river behind the room was great"
The price is SAR 390
SAR 590 total
includes taxes & fees
1 May - 2 May
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)
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

Killington area home - 4-seasons & hot tub. Sleeps 13+

9.8 out of 10, Exceptional, (117)
"Had a great stay in the perfect ski house "
Killington area home - 4-seasons & hot tub. Sleeps 13+

Private Killington Area Inn all to Yourself!

10.0 out of 10, Exceptional, (38)
"Eric is a perfect host! The inn is perfect, 9 rooms, private bathrooms. The kitchen is awesome, great appliances and big enough for everyone to be in the kitchen at the same time. This was our third year with family staying and celebrating. We will be back!"
Private Killington Area Inn all to Yourself!

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.