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
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is AU$621 per night from 30 Nov to 1 Dec
AU$621
30 Nov - 1 Dec
includes taxes & fees
9.2/10 Wonderful! (551 reviews)
Clean room, Awesome staff and always a good vibe.
Reviewed on 17 Nov 2025
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is AU$247 per night from 3 Dec to 4 Dec
AU$247
3 Dec - 4 Dec
includes taxes & fees
7.2/10 Good! (1,003 reviews)
Great staff and a beautiful place to stay
Reviewed on 17 Nov 2025
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is AU$237 per night from 30 Nov to 1 Dec
AU$237
30 Nov - 1 Dec
includes taxes & fees
9/10 Wonderful! (949 reviews)
The front desk staff are patient and enthusiastic.
Reviewed on 24 Nov 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.
