
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 area home - 4-seasons, hot tub and A/C
Pittsfield VT
9.8/10 Exceptional! (124 reviews)
the house was great, and we especially enjoyed the pool table, hot tub, fireplace, and dart board. david was an excellent host and his property manager dave bascomb was also fantastic. 6 inches of snow came 2 days later, and our SUV with AWD couldn’t handle the uphill to the house, and we got stuck ...
Reviewed on 22 Feb 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is AU$238 per night from 23 Apr to 24 Apr
AU$238
23 Apr - 24 Apr
includes taxes & fees
7.4/10 Good! (1,001 reviews)
it was good
Reviewed on 8 Apr 2026

Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is AU$597 per night from 30 Apr to 1 May
AU$597
30 Apr - 1 May
includes taxes & fees
9.4/10 Exceptional! (572 reviews)
Wonderful historic property with warm and thoughtful staff. Even though some areas in the lobby were being refurbished, we still enjoyed the experience. Look forward to returning when the huge fireplace in the lobby is back up and operational.
Reviewed on 10 Apr 2026
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.











