4 Star Hotels in Ashuwillticook Rail Trail, 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 availability on Ashuwillticook Rail Trail 4 Star Hotels

Tonight
24 Jul - 25 Jul
Tomorrow
25 Jul - 26 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Top Ashuwillticook Rail Trail 4 Star Hotels

The Williams Inn
Stunning hotel with a blend of traditional and modern architecture, surrounded by beautifully maintained gardens and a serene water feature.

The Williams Inn

4.0 star property
9.6 out of 10, Exceptional, (473)
"Wonderful stay. Helpful, professional staff. "
The price is €255
includes taxes & fees
13 Aug - 14 Aug
The Williams Inn
South Shire
Enter a grand space with a beautiful staircase, adorned with floral patterns and a statement mirror.

South Shire

4.0 star property
9.2 out of 10, Wonderful, (88)
"very nice highly recommend "
The price is €156
includes taxes & fees
5 Aug - 6 Aug
South Shire
The Central Downtown Inn & Suites
Compact kitchen with modern design, featuring white and wood cabinetry, refrigerator, coffee maker, and toaster.

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 €122
includes taxes & fees
31 Jul - 1 Aug
The Central Downtown Inn & Suites
Lakehouse Inn
Relax on the deck with a glass of wine, taking in the serene views of the surrounding water and lush landscape.

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (273)
"Great Views & Hospitality"
Lakehouse Inn
Devonfield Inn B&B
Stunning two-story house with a central entrance and beautifully manicured lawn.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
33 Main
Features a sleek glass-enclosed shower, vanity with sink and mirror, toilet, and bidet.

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
33 Main
Seven Hills Inn
Enjoy meals in this elegant dining area with a central round table and comfortable seating.

Seven Hills Inn

4.0 star property
7.8 out of 10, Good, (467)
"Great location, nice breakfast and clean rooms"
Seven Hills Inn
The Four Chimneys Inn
Classic design bedroom with a large bed, armchairs, and a stylish table.

The Four Chimneys Inn

4.0 star property
9.4 out of 10, Exceptional, (276)
"Nice and cozy"
The Four Chimneys Inn
The Inn at Stockbridge
Stroll through the serene park and enjoy the soothing sounds of the multi-tiered fountain surrounded by lush trees and a shaded walkway.

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Enjoy meals in this inviting dining room with a large table, comfortable chairs, and ample natural light.

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is €448
includes taxes & fees
4 Aug - 5 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
General Williams Estate House Lenox/Stockbridge
Two houses sit amidst a well-manicured lawn and lush trees.

General Williams Estate House Lenox/Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (110)
"The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot."
General Williams Estate House Lenox/Stockbridge
Hampton Terrace Inn
Welcome to this charming two-story house with a cozy front porch and balcony, featuring a wreath above the door and green shutters.

Hampton Terrace Inn

4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
The price is €333
includes taxes & fees
24 Aug - 25 Aug
Hampton Terrace Inn
Garden Gables Inn
Stunning mountain retreat with a spacious porch and multiple windows, surrounded by snow-covered trees and a well-lit pathway.

Garden Gables Inn

4.0 star property
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. "
Garden Gables Inn
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Ashuwillticook Rail Trail

Venture 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

Top Ashuwillticook Rail Trail Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"We did not care for the barn door to the bathroom. Wouldn't stay closed and large gap meant a loud radio or TV required... Otherwise, our stay was great and we would definitely recommend it."
Carrie 1-night trip
Posted 2 days ago
The Williams Inn