Pittsfield Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$703 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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$570 per night from 22 Feb to 23 Feb
AU$570
22 Feb - 23 Feb
includes taxes & fees
9.2/10 Wonderful! (560 reviews)
Luxurious and friendly resort! Loved it
Reviewed on 18 Dec 2025
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is AU$297 per night from 22 Feb to 23 Feb
AU$297
22 Feb - 23 Feb
includes taxes & fees
7.2/10 Good! (1,003 reviews)
Solid accommodations.
Reviewed on 12 Jan 2026
Comfort Inn Rutland - Killington
19 Allen St Rutland VT
Fully refundableReserve now, pay when you stay
The price is AU$228 per night from 1 Feb to 2 Feb
AU$228
1 Feb - 2 Feb
includes taxes & fees
8/10 Very Good! (1,003 reviews)
Yea
Reviewed on 18 Jan 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
