Hotels in Pittsfield

Free cancellation options if plans change
Unlock travel rewards with One Key
Save more with Member Prices

Check prices for these dates

Tonight
Feb 14 - Feb 15
Tomorrow
Feb 15 - Feb 16
This weekend
Feb 14 - Feb 16
Next weekend
Feb 21 - Feb 23

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, (126)
The price is $182
includes taxes & fees
$165 per night
Feb 23 - Feb 24
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.
On a rooftop patio

Use code VALENPOWER for an extra 10% off your next getaway

One Key™ members get an extra 10% off hotels, book by Feb 17, travel between Feb 6 through Aug 31 (US customers only).*T&Cs apply

Learn more about Pittsfield

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

See all hotels in Pittsfield

Frequently asked questions

What accommodations do travelers recommend in Pittsfield?
Guests like Killington Mountain Lodge, Tapestry Collection by Hilton, Summit Lodge and Mountain Sports Inn.
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.