Search Guest Houses in Pittsfield

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

The Trailside Inn
Family Suite, Private Bathroom (Queen Bed and 3 Twin Beds) | Iron/ironing board, free WiFi, bed sheets

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 price is AED 585
AED 644 total
includes taxes & fees
2 Jun - 3 Jun
The Trailside Inn
The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views!
Smart TV

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 AED 1,418
AED 3,227 total
includes taxes & fees
5 May - 6 May
The Slopeside Estate Guesthouse: Ski On/Off, Hot Tub, Views!
Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts
Internet, bed sheets

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
Fridge, microwave, oven, stovetop

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
Exterior

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 AED 382
AED 578 total
includes taxes & fees
18 May - 19 May
110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool
Salt Ash Inn
Billiards

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+
Property grounds

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!
Fridge, microwave, oven, stovetop

Private Killington Area Inn all to Yourself!

10.0 out of 10, Exceptional, (38)
"Overall fabulous place to stay. Will be back next year!!"
Private Killington Area Inn all to Yourself!
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
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.