Hotels in Pittsfield

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Tonight
May 7 - May 8
Tomorrow
May 8 - May 9
This weekend
May 9 - May 11
Next weekend
May 16 - May 18

Where to stay in Pittsfield?

The Trailside Inn
Family Suite, Private Bathroom (Queen Bed and 3 Twin Beds) | Iron/ironing board, free WiFi, bed sheets

The Trailside Inn

3.0 star property
9.0 out of 10, Wonderful, (130)
The price is $175
includes taxes & fees
$159 per night
Jun 2 - Jun 3
The Trailside Inn
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.

Top landmarks in Pittsfield

Roger Clark Memorial Central Library

Roger Clark Memorial Central Library is worth a visit when in central Pittsfield.

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Roger Clark Memorial Central Library

Pittsfield Town Hall

Pittsfield Town Hall is worth a visit when in central Pittsfield.

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Pittsfield Town Hall

Learn more about Pittsfield

Pittsfield is well-known for its attractions such as Green Mountain National Forest and Roger Clark Memorial Central Library.

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A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
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Frequently asked questions

What accommodations do travelers recommend in Pittsfield?
Guests like Killington Mountain Lodge, Tapestry Collection by Hilton, The Mountain Inn at Killington and North Star Lodge and Resort.
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 38 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.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

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