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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Featured Guest Houses in Western Massachusetts

Blooming Inn
Front of property

Blooming Inn

3.0 star property
9.2 out of 10, Wonderful, (76)
"Totally enjoyed our stay here. Just a short walk to a lovely downtown area with various dining options. We will definitely stay here again "
The price is AU$208
includes taxes & fees
3 Feb - 4 Feb
Blooming Inn
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (270)
"This was a perfect no fuss property in the denser business area of Pittsfield. I suggest this area over the residential areas. Room was really great. There is a separate bedroom with it's own tv. The furniture and bed are not the newest or most luxurious, but they are comfortable. Stayed comfortably for 3 nights to attend Tanglewood shows. Self-check in was easy and great for people who are coming in after doing a lot of things on the trip in. Would definitely stay again."
The Central Downtown Inn & Suites
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!
Fridge, microwave, oven, stovetop

The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

9.8 out of 10, Exceptional, (85)
"Great place, they though of everything."
The price is AU$392
includes taxes & fees
3 Feb - 4 Feb
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!
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, (97)
"It is so clean and cozy to sleep here. I love the local town and proximity to great slopes."
The price is AU$255
includes taxes & fees
5 Feb - 6 Feb
In town, newly remodeled studio with private balcony
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)
"So clean and comfy"
The price is AU$613
includes taxes & fees
3 Feb - 4 Feb
Upscaled Home in a Quiet Neighborhood
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
Guest House Sanctuary by Evergreen Home
Interior

Guest House Sanctuary by Evergreen Home

Guest House Sanctuary by Evergreen Home
Orchard Guest House: Cozy Berkshire Retreat in the Woods
Living area

Orchard Guest House: Cozy Berkshire Retreat in the Woods

The price is AU$557
includes taxes & fees
1 Mar - 2 Mar
Orchard Guest House: Cozy Berkshire Retreat in the Woods
Jacob's Tanglewood Ranch
Dishwasher

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch
Chestnut Lodge
Exterior

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
Angels Rest Retreat
View from property

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
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.
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Other property types in Western Massachusetts

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is AU$281
includes taxes & fees
3 Feb - 4 Feb
Vacation Village in the Berkshires
The Ponds at Foxhollow by Capital Vacations
Property grounds

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is AU$430
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (924)
"Staff was exceptionally helpful and friendly."
The price is AU$333
includes taxes & fees
3 Feb - 4 Feb
Jiminy Peak Mountain Resort
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.