Pittsfield Packages (Flight + Hotel)
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Top hotels in Pittsfield
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is ฿13,275 per night from 1 Sept to 2 Sept
฿13,275
฿16,031 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! (801 reviews)
Get away to Vermont
"Nice get away spit in the country. Very clean and bed was comfortable. Fire pits were lite each night to sit out and enjoy. Short walk into town for shopping and eating. A market across the road was very convenient."
Reviewed on 14 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 ฿3,283 per night from 19 Aug to 20 Aug
฿3,283
฿3,611 total
19 Aug - 20 Aug
includes taxes & fees
6.2/10 (1,002 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.