Western Massachusetts Guest Houses

A lake with a rocky shoreline and a forested island.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Western Massachusetts guest houses

A two-story house with a porch, a balcony, and a chimney.

1. Blooming Inn

Shelburne Falls

steven

P9,542 total

includes taxes & fees

Oct 27 - Oct 28

A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.

2. Hideaway Inn Lenox

Lenox

Barbara

P9,586 total

includes taxes & fees

Nov 2 - Nov 3

A living room with a fireplace, two sofas, and four black side tables.

3. The Revival House

Adams

Katrina

P10,486 total

includes taxes & fees

Nov 2 - Nov 3

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

4. The Central Downtown Inn & Suites

Pittsfield

Rena

P6,917 total

includes taxes & fees

Oct 5 - Oct 6

A stainless steel refrigerator with a digital display showing the time and date, a microwave above it, and a kettle on the stove.

5. Upscaled Home in a Quiet Neighborhood

Forest Park

Anonymous traveler

P30,486 total

includes taxes & fees

Oct 4 - Oct 5

A historic brick building with a porch and a sign reading "Burrell House."

6. The Burrell House

Keene

Justin

P9,548 total

includes taxes & fees

Oct 21 - Oct 22

A two-story house with a stone staircase leading to a wooden front door.

7. The Inn At Quail Run

Wilmington

Chandra

P13,417 total

includes taxes & fees

Nov 1 - Nov 2

A dining area with wooden tables and chairs, large windows with white frames, and wall-mounted light fixtures.

8. Cornwall Inn and Lodge

Cornwall Bridge

Richard T

P15,221 total

includes taxes & fees

Nov 1 - Nov 2

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Western Massachusetts Hotel Reviews

The Yankee Inn

10/10 Excellent

"I can’t say enough about the care we received at the Yankee Inn. We stayed one night on the second day of a two-week tour of the Northeast. The room was clean and well equipped, the beds and pillows were comfortable, and breakfast included eggs, sausage, and a waffle maker. But what truly stood out was the care and concern George at the front desk showed us. Just after we checked out, the check engine light and several other warning lights came on in our two-month-old Subaru. I hoped Subaru could provide a quick diagnosis, but the only help they offered was a tow to the nearest dealership. We had no idea what to do. If the dealership had to keep the car for diagnosis, we could be stranded for days. When we asked George whether a room would be available if we needed to stay another night, he said the hotel had only one left. Because we still didn’t know what would happen with the car, he offered to hold it until we knew whether we needed it. He also opened the lounge so we could store the luggage we had to remove before the car was towed. He made us feel welcome and went out of his way to help in every way he could. Fortunately, the dealership identified the problem, and we drove away that afternoon to continue our trip. The room and breakfast were great, but the Yankee Inn’s extraordinary kindness is what would bring us back!"

Find out more about Western Massachusetts