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Find 4 Star Hotels in Ashuwillticook Rail Trail, MA from ￥15,462

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Check availability on Ashuwillticook Rail Trail 4 Star Hotels

Our top choices for Ashuwillticook Rail Trail 4-star hotels

Front of property - evening/night
The Williams Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (549)
"Nice place to stay for a wedding "
United States
Timothy
The price is ￥30,552
￥34,126 total
includes taxes & fees
Dec 17 - Dec 18
The Williams Inn
Balcony
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ￥13,842
￥15,462 total
includes taxes & fees
Dec 17 - Dec 18
The Central Downtown Inn & Suites
Library
South Shire

South Shire

South Shire
4.0 star property
Bennington
9.2 out of 10, Wonderful, (118)
"Great period decor! Spacious rooms and an inviting living room to relax. Also walking distance to downtown shops and restaurants was a real plus!"
United States
Roseann
The price is ￥25,029
￥28,972 total
includes taxes & fees
Dec 24 - Dec 25
South Shire
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is ￥27,075
￥31,757 total
includes taxes & fees
Dec 19 - Dec 20
Lakehouse Inn
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Front of property
Seven Hills Inn

Seven Hills Inn

Seven Hills Inn
4.0 star property
Lenox
7.8 out of 10, Good, (467)
"Great location, nice breakfast and clean rooms"
United States
Christopher
Seven Hills Inn
Suite, Private Bathroom (RedBird Suite) | View from room
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is ￥59,201
￥71,616 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Signature Room, King plus Twin Bed, Private Bathroom, Porch, Accessible, RM-10 | Premium bedding, individually decorated, individually furnished
The Four Chimneys Inn

The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (280)
"What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite. "
United States
Jon
The Four Chimneys Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is ￥64,301
￥71,825 total
includes taxes & fees
Jan 11 - Jan 12, 2026
33 Main
Exterior
General Williams Estate House Lenox/Stockbridge

General Williams Estate House Lenox/Stockbridge

General Williams Estate House Lenox/Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (111)
"The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot."
United States
Joanna T.
General Williams Estate House Lenox/Stockbridge
Exterior detail
Hampton Terrace Inn

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (43)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
United States
Abby
The price is ￥40,752
￥45,520 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Hampton Terrace Inn
Front of property
The Inn at Stockbridge

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is ￥38,877
￥45,599 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Inn at Stockbridge
Front of property - evening/night
Garden Gables Inn

Garden Gables Inn

Garden Gables Inn
4.0 star property
Lenox
9.2 out of 10, Wonderful, (57)
"Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. "
United States
john
Garden Gables Inn
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Learn more about Ashuwillticook Rail Trail

Head to Mount Greylock State Reservation Visitor Center and Wahconah Falls State Park—just two of the sights around Ashuwillticook Rail Trail.

See all hotels in Ashuwillticook Rail Trail
The Ashuwillticook Rail Trail

Top Ashuwillticook Rail Trail Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick. "
Stacey 1-night trip
Posted 9 days ago
The Williams Inn

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