Search Inns in Pittsfield from CA $141

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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

Browse Select Pittsfield Inns

Summit Lodge
Fireplace

Summit Lodge

3.0 star property
8.6 out of 10, Excellent, (386)
"They have very good breakfast in the morning."
Summit Lodge
The Village Inn of Woodstock
Garden

The Village Inn of Woodstock

4.0 star property
9.8 out of 10, Exceptional, (86)
"From the moment we arrived, Heather welcomed us and helped us have a relaxing stay. Our bed was very comfy and the shower had great water pressure. The tap water tasted like spring water! Delicious! Close to the village, there’s also a small market next door where we bought sandwiches for lunch. Heather’s breakfasts were gourmet amazing! "
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)
"Online it says it has an EV charging station but it doesn't. But not too much of a setback otherwise the place was very cute and hospitable! Great Vermont charm! "
Waybury Inn
Clear River Inn
Restaurant

Clear River Inn

3.0 star property
8.8 out of 10, Excellent, (85)
"Staff was very professional and friendly! River the Inn was beautiful! "
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)
" Lincoln Inn and Gallery Apr 2025 • Couples Beautiful location on the Ottauquechee River in Woodstock, Vermont. The one-of-a-kind Lincoln covered bridge abuts the property. The owners and family are warm and very accommodating. Our unit had a fully stocked kitchen with full-size stove and refrigerator. The king size bed was new and very comfortable. There is an art gallery on site with beautiful paintings done by the 17 year old daughter of the owners. @gracescarletart on Instagram. Outside,...
The price is CA $141
CA $155 total
includes taxes & fees
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)
"We stayed at this property for a ski weekend in March. 8 guys fit comfortably and the accommodations were perfect. Property was as advertised and very clean. We enjoyed the hot tub after hitting the slopes which was a great way to finish the day. Owner was very accommodating and quick to reply to any inquiries or questions. 10/10"
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)
"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
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)
"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.