
Pittsfield Packages (Flight + Hotel)
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Top hotels in Pittsfield

Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is ฿13,225 per night from 1 Sept to 2 Sept
฿13,225
฿15,971 total
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (531 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."
Reviewed on 30 Jul 2025

The Shire Woodstock
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (796 reviews)
"Beautiful pet friendly place in the heart of Woodstock Village. Scenery is lovely, soothing and plenty to do. Can walk to things, bike or hike."
Reviewed on 1 Aug 2025

Days Inn by Wyndham Rutland/Killington Area
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is ฿3,271 per night from 18 Aug to 19 Aug
฿3,271
฿3,598 total
18 Aug - 19 Aug
includes taxes & fees
6.2/10 (1,001 reviews)
"Staff was friendly and helpful. Nice breakfast. Comfortable bed. The bathroom needed some maintenance such as new calking around the tub. A little mildew. Ok for one night."
Reviewed on 10 Aug 2025
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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