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Check prices for these dates

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

Compare 9 Inns in Pittsfield with updated reviews, rates, and availability.

Summit Lodge
Fireplace

Summit Lodge

3.0 star property
8.6 out of 10, Excellent, (386)
"Love the old ski lodge feel and the layout of the hotel"
Summit Lodge
The Village Inn of Woodstock
Garden

The Village Inn of Woodstock

4.0 star property
9.8 out of 10, Exceptional, (86)
"Great place for a quiet getaway, while being conveniently located next to a grocery store and walking distance to downtown Woodstock and Billings farm. Excellent breakfast too."
The Village Inn of Woodstock
Kedron Valley Inn
Exterior

Kedron Valley Inn

3.5 star property
9.0 out of 10, Wonderful, (307)
"Good experience . Loved the proximity of Country store. We had breakfast there x 3 "
Kedron Valley Inn
Waybury Inn
Interior

Waybury Inn

3.5 star property
9.2 out of 10, Wonderful, (69)
"Wonderful authentic stay with lovely staff, great food, and a cozy inviting atmosphere. Would definitely stay again!"
Waybury Inn
Clear River Inn
Restaurant

Clear River Inn

3.0 star property
8.8 out of 10, Excellent, (85)
Clear River Inn
Birch Ridge Inn
Front of property

Birch Ridge Inn

3.0 star property
9.6 out of 10, Exceptional, (164)
"Nice place to stay"
Birch Ridge Inn
Fox Creek Inn LLC
Exterior

Fox Creek Inn LLC

3.0 star property
Fox Creek Inn LLC
Lincoln Inn & Gallery
BBQ/picnic area

Lincoln Inn & Gallery

3.0 star property
10.0 out of 10, Exceptional, (4)
"We had a wonderful stay at the Lincoln Inn. The property was very cute and historic, and the innkeeper was warm and welcoming."
The price is $112
includes taxes & fees
$102 per night
May 11 - May 12
Lincoln Inn & Gallery
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.