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Ashuwillticook Rail Trail 4 Stars Hotels

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Check availability on Ashuwillticook Rail Trail 4 Star Hotels

Tonight
Dec 31 - Jan 1
Tomorrow
Jan 1 - Jan 2
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

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, (556)
"Great staff, great rooms, we had a little issue with the door not opening, but they were quick to fix it. Bar staff, fantastic! Restaurant (we had brunch) delicious. This is our go to hotel when we stay in the Berkshires "
United States
James
The price is ₩281,790
₩314,759 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Williams Inn
Microwave, oven, stovetop, dishwasher
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, (348)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is ₩134,390
₩150,116 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Central Downtown Inn & Suites
Reception
South Shire

South Shire

South Shire
4.0 star property
Bennington
9.2 out of 10, Wonderful, (119)
"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 ₩250,909
₩289,075 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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 ₩264,892
₩310,680 total
includes taxes & fees
Jan 15 - Jan 16, 2026
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
Business center
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 ₩546,023
₩660,532 total
includes taxes & fees
Jan 13 - Jan 14, 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 ₩572,229
₩639,181 total
includes taxes & fees
Jan 18 - Jan 19, 2026
33 Main
Exterior
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 ₩312,957
₩349,571 total
includes taxes & fees
Jan 20 - Jan 21, 2026
Hampton Terrace Inn
Exterior
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 ₩358,564
₩420,555 total
includes taxes & fees
Jan 5 - Jan 6, 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 Mount Greylock—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