Hotels in Pittsfield

your current months are January, 2025 and February, 2025.
January 2025
February 2025

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Where to stay in Pittsfield?

Winding Way Chalet 3 Bedroom Home
House, 3 Bedrooms | Property grounds

Winding Way Chalet 3 Bedroom Home

3.0 star property
Winding Way Chalet 3 Bedroom Home
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.

Learn more about Pittsfield

The region around Pittsfield is home to attractions such as Green Mountain National Forest and Pico Mountain at Killington Ski Resort.

See all hotels in Pittsfield

Frequently asked questions

Can I book a refundable accommodation in Pittsfield?
If you need the flexibility to change your travel plans to Pittsfield, most accommodations provide refundable* rates you can book. You can see these accommodations by searching our site and using the “fully refundable” filter to narrow down the results.
Where can I stay with my pet in Pittsfield?
Your animal companion is welcome at this pet-friendly hotel: Clear River Inn.
Where can I stay in Pittsfield if I want a vacation home instead of a hotel?
If you want a good alternative to a hotel, review our selection of 36 vacation homes.
Where can I stay if I'm visiting Pittsfield with my family?
Your kids are welcome at Clear River Inn.
What will the weather in Pittsfield be like during my trip?
The warmest months in Pittsfield are usually July and August with an average temp of 63°F. January and February are the chilliest months when the average temp is 23°F. The rainiest months are July and June.
Why should I book my Pittsfield hotel with Hotels.com?
There are plenty of reasons to book your Pittsfield travel with us: our free cancellations on selected hotels* gives you the flexibility you’re looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.