Search Guest Houses in Western Massachusetts

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Guest Houses in Western Massachusetts and around

Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (109)
"Lovely Inn and very responsive and approachable staff. "
The price is €127
includes taxes & fees
12 Aug - 13 Aug
Blooming Inn
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (320)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is €166
includes taxes & fees
3 Sept - 4 Sept
The Dewey
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (299)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is €110
includes taxes & fees
1 Sept - 2 Sept
The Central Downtown Inn & Suites
The Revival House
Romantic Room, 1 King Bed (Room 4)

The Revival House

3.0 star property
9.6 out of 10, Exceptional, (8)
"Beautifully renovated historical bed and breakfast that offers historical details along with modern touches. Our room was spacious and very clean and common areas are appointed with great attention to detail. "
The price is €172
includes taxes & fees
10 Aug - 11 Aug
The Revival House
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (254)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
Berkshire Village Carriage House - Super Private!!
Upscaled Home in a Quiet Neighborhood
Flat-screen TV, fireplace

Upscaled Home in a Quiet Neighborhood

3.0 star property
8.4 out of 10, Very good, (5)
The price is €418
includes taxes & fees
9 Aug - 10 Aug
Upscaled Home in a Quiet Neighborhood
In town, newly remodeled studio with private balcony
Smart TV, Netflix, streaming services

In town, newly remodeled studio with private balcony

10.0 out of 10, Exceptional, (113)
"Great place. Quiet, clean and spacious - thank you so much "
In town, newly remodeled studio with private balcony
Renovated Private Guest House by Evergreen Home
Outdoor dining

Renovated Private Guest House by Evergreen Home

10.0 out of 10, Exceptional, (9)
"Great stay. Cute spot!"
Renovated Private Guest House by Evergreen Home
Jacob's Tanglewood Ranch
Dishwasher

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch
Cliffwood Cottage by Evergreen Home
Interior

Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home
Angels Rest Retreat
Property amenity

Angels Rest Retreat

3.0 star property
10.0 out of 10, Exceptional, (1)
"Angel's Rest is sooo peaceful. We had a delicious and super healthy breakfast in the breakfast nook, surrounded by lovely plants and a small fountain, looking out over the rolling hills of Western Mass. The fall colors were nice. "
Angels Rest Retreat
Chestnut Lodge
Property grounds

Chestnut Lodge

3.5 star property
2.0 out of 10, (2)
"An absolutely horrible experience! My family (2 adults and my 6 year old son) had reserved this so-called hotel for $284 in June for a 13th Aug stay. After a full day at the Berkshires, we checked-in at 6 pm. This place is in a terrible location (unpaved roads, still-in construction steps). To our horror we found that the room had No Air-Conditioning. It was 90 degrees outside and all they had in the room was a ceiling fan. There were bugs in the room due to the heat. On top of it all the...
Chestnut Lodge
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Western Massachusetts Hotel Reviews

Inn on Boltwood

Inn on Boltwood

10/10 Excellent
"Beautiful place. Comfortable bed. "
Tamara 1-night trip
Posted 2 days ago
Inn on Boltwood