Hotels in Pittsfield

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Where to stay in Pittsfield?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Pittsfield on Hotels.com. These Pittsfield hotels consistently deliver on quality, location and traveler experience. Last updated on September 2, 2026.

Mountain Meadows Lodge

Killington

CNY1,104

CNY1,382 total

includes taxes & fees

Sep 13 - Sep 14

North Star Lodge and Resort

Killington

CNY698

CNY768 total

includes taxes & fees

Sep 3 - Sep 4

The Mountain Inn at Killington

Killington

CNY701

CNY809 total

includes taxes & fees

Sep 3 - Sep 4

The Trailside Inn

North Sherburne

CNY1,070

CNY1,177 total

includes taxes & fees

Sep 14 - Sep 15

Suite, 1 King Bed, Jetted Tub | Living area

Hampton Inn Rutland

Rutland

CNY931

CNY1,024 total

includes taxes & fees

Sep 9 - Sep 10

Greenbrier Inn

Killington

CNY980

CNY1,129 total

includes taxes & fees

Sep 3 - Sep 4

The Mountain Top Inn & Resort

Chittenden

CNY1,856

CNY2,023 total

includes taxes & fees

Sep 14 - Sep 15

Premium Suite, Multiple Beds | Living area

Mountain Sports Inn

Killington

CNY623

CNY685 total

includes taxes & fees

Sep 3 - Sep 4

Best Western Inn & Suites Rutland-Killington

Rutland

CNY1,203

CNY1,324 total

includes taxes & fees

Sep 13 - Sep 14

Comfort Inn Rutland - Killington

Rutland

CNY927

CNY1,019 total

includes taxes & fees

Sep 9 - Sep 10

Summit Lodge

Killington

CNY978

CNY1,210 total

includes taxes & fees

Sep 12 - Sep 13

My Place Hotel-Randolph VT

Randolph Center

CNY1,170

CNY1,275 total

includes taxes & fees

Sep 3 - Sep 4

Inn at Neshobe River

Brandon

CNY1,176

CNY1,293 total

includes taxes & fees

Sep 15 - Sep 16

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington

CNY1,068

CNY1,175 total

includes taxes & fees

Sep 7 - Sep 8

Après Inn Killington

Killington

CNY696

CNY765 total

includes taxes & fees

Sep 7 - Sep 8

Room, 2 Queen Beds, Wheelchair Accessible, Non Smoking

Days Inn by Wyndham Rutland/Killington Area

Rutland

CNY822

CNY905 total

includes taxes & fees

Sep 8 - Sep 9

Turn of River Lodge

Killington

CNY666

CNY732 total

includes taxes & fees

Sep 10 - Sep 11

Snowed Inn

Killington

CNY853

CNY1,033 total

includes taxes & fees

Sep 13 - Sep 14

Family Cabin, 2 Queen Beds | Room amenity

Emrose Luxury Cabins

Brandon

CNY1,089

CNY1,230 total

includes taxes & fees

Sep 15 - Sep 16

Brandon Inn

Brandon

CNY760

CNY836 total

includes taxes & fees

Sep 3 - Sep 4

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Go beyond your typical stay in Pittsfield

Pet friendly

Apartment

Pool

Cottage

Family friendly

Condo

Hot tub

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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Pittsfield Town Hall

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

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Learn more about Pittsfield

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

See all hotels in Pittsfield

A lake surrounded by autumn-colored trees and a rocky shoreline.

Check out reviews of Pittsfield hotels guests love

Emrose Luxury Cabins

10/10 Excellent

"Very clean cabin and got everything we needed"

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent

"Very quiet, great ac. Pool was great"

Hampton Inn Rutland

10/10 Excellent

"Great hotel, not there long enough to use amenities. Very expensive for area we thought. But definitely nice!"

On The River Inn

10/10 Excellent

"We had a wonderful stay at On the River. The room was large, clean, and very quiet. It's a short, quick drive into town. The staff was pleasant and helpful. A good choice when staying near Woodstock."

Woodstock Inn & Resort

10/10 Excellent

"Our room was beautiful, clean, and quiet. The bed was comfortable, and the amenities in the bathroom were a real indulgence."

My Place Hotel-Randolph VT

10/10 Excellent

"Very nice hotel. We would stay there again."

North Star Lodge and Resort

8/10 Good

"Room alittle dates. Some updating should be done throughout. But all around nice place."

The Shire Woodstock

10/10 Excellent

"Great Location. great views of the river, lawn and firepits for relaxing. Rooms recently redone and well done."

The Jackson

10/10 Excellent

"Love this B&B - very well located, the food is amazing and the bedrooms are very comfy! Highly recommend!"

Frequently asked questions

How much does a hotel room cost in Pittsfield?

You can discover great hotels in Pittsfield from CNY685 with properties to suit all budgets and needs. To find an affordable hotel in Pittsfield that meets all of your requirements, just apply filters on Hotels.com and sort hotels by "Price: low to high".

How can I find deals and earn rewards at Pittsfield hotels?

Discover great deals on Pittsfield hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Pittsfield hotels.

Can I book Pittsfield hotels with free cancellation?

It's easy to book a refundable Pittsfield hotel on Hotels.com. Simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some top pet-friendly hotels in Pittsfield?

Consider one of our travelers' favorite pet-friendly hotels in Pittsfield:

Clear River Inn: An inn with a guest rating of 8.8 out of 10

You can check "Pet friendly" on the Hotels.com "Amenities" filter in your search to find even more pet-friendly hotels in Pittsfield.

What are some of the best Pittsfield hotels with free parking?

If you're exploring by car, finding a great Pittsfield hotel with free parking is a win. Our travelers' favorites include:

Clear River Inn: An inn with an average guest rating of 8.8 out of 10

What are some popular hotels in central Pittsfield?

If you're looking for hotels in central Pittsfield, check out Clear River Inn. Travelers love Clear River Inn for its location, as well as the restaurant, bar/lounge and nightclub this inn offers. North Sherburne is a central neighborhood for your Pittsfield vacation.

What accommodations do travelers recommend in Pittsfield?

Guests like The Mountain Inn at Killington, Killington Mountain Lodge, Tapestry Collection by Hilton and Mountain Meadows Lodge.

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 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 28 vacation homes.

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.

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