Search for Cheap Deals onHotels in Pittsfield
Choose from 1849 Pittsfield Hotel Deals
The Mountain Inn at Killington
"The property is beautiful and it’s convenient to the golf course. The rooms small but clean. Not a lot of privacy in the bathroom due to sliding door. Also, no coffee machines in the room"
Reviewed on Sep 25, 2026
Woodstock Inn & Resort
"Wonderful inn! Everything was wonderful: rooms, food, etc!!"
Reviewed on Sep 22, 2026
Killington Mountain Lodge, Tapestry Collection by Hilton
"Great outdoor hot tub"
Reviewed on Sep 25, 2026
The Jackson
"The Hostess at the wine and cheese hour was very kind and helpful. That was the only time we saw anyone! The house is divided into separate areas and we were in the oldest part. The bed was comfortable, bathroom nice, amenities nice but wouldn’t book again because of the very narrow and steep stairs. ..."
Reviewed on Sep 21, 2026
Emrose Luxury Cabins
"This is a unique property. Very clean, great shampoos, comfortable beds. Bring your own food and snacks. The grounds are super clean and in a safe, private area. We had an issue with the arrival instructions not opening in email but a call to the property phone number got our issue resolved quickly. ..."
Reviewed on Sep 26, 2026
My Place Hotel-Randolph VT
Mountain Meadows Lodge
"This place was beautifully decorated. Bed was very comfortable, hot tub, and sitting by the lake was phenomenal. The community jigsaw puzzle was a nice touch. The breakfast was delicious and a staff of super nice. We’ve never had an experience like that at a hotel."
Reviewed on Sep 25, 2026
Mountain Sports Inn
"Jenny @ the front desk was very helpful and kind. The hotel itself is dated. Older beds. Stark shelving in bathrooms though functional. Breakfast was hot and fresh, cook was not.. 😆. Overall we enjoyed our stay and would stay again. Probably request a room away from the main door and towards the ..."
Reviewed on Sep 21, 2026
The Shire Woodstock
"Great views"
Reviewed on Sep 25, 2026
On The River Inn
"It’s over priced for a hotel requires us to drive to Woodstock and its restaurants and amenities. Although it was not full we were allocated a room at far end of the hotel where WiFi was poor and the room was a bit smaller because stairway next to the room took out part of the space.The pool and ..."
Reviewed on Sep 26, 2026
Brandon Inn
"Beautiful"
Reviewed on Sep 24, 2026
Comfort Inn Rutland - Killington
"Only there for one night. Good clean room with friendly and knowledgeable staff."
Reviewed on Sep 25, 2026
Find cheap hotels in Pittsfield
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- Hotels near Killington Resort
- Hotels near Green Mountain National Forest
- Hotels near Pico Mountain at Killington Ski Resort
- Hotels near Middlebury College
- Hotels near Mad River Valley
- Hotels near Killington Peak
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