Pittsfield Holidays
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Your Pittsfield Holiday
With everything planned before you take off, our Pittsfield holiday packages mean you can simply focus on enjoying your getaway. Whether you're going to be based in the neighbourhood of West Bridgewater, which is good for skiing, or somewhere else in town, this lively city promises an array of discoveries. Appalachian Trail Adventures, Green Mountain National Golf Course and Lefferts Pond are just some of the many attractions worth exploring during your trip to Pittsfield. Whatever your travel plans or budget, organising a tailored Pittsfield holiday is easy with Expedia.
Pittsfield Holiday
Pittsfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rutland Southern Vermont Regional Airport (RUT) |
Population | 540 |
Max Temp Winter | -3.89ºC |
Max Temp Summer | 24ºC |
Top Sights | Pico Mountain at Killington Ski Resort, Killington Peak and Killington Adventure Centre |
Our pick of the best Pittsfield Hotel Deals
Killington Vermont Ski and Snowmobiling House
Pittsfield
9/10 Wonderful! (38 reviews)
Amazing stay!
"Was not listed that soaps and toilet paper is not included. Just would’ve preferred that be out in the listing"
Reviewed on 13 Mar 2025
The Shire Woodstock
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (840 reviews)
"Had road view but was ok for the amount of time spent there. Located in perfect spot for easy walking to grocery store and downtown shopping. Hotel offers complimentary Coffee Bar, waters, cookies and even bicycles to ride"
Reviewed on 6 Oct 2025
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is AU$753 per night from 10 Nov to 11 Nov
AU$753
10 Nov - 11 Nov
includes taxes & fees
9.2/10 Wonderful! (536 reviews)
"Very nice property. Would love to visit again."
Reviewed on 7 Oct 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
