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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Ashuwillticook Rail Trail bed & breakfast

A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.

1. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
The price is Rp2.991.196
Rp3.350.140 total
includes taxes & fees
3 Dec - 4 Dec
Inn at Silver Maple Farm
A breakfast setting with a plate of food, a glass of orange juice, and a cup of tea.

2. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.8 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is Rp4.604.401
Rp4.866.852 total
includes taxes & fees
7 Dec - 8 Dec
Harbour House Inn
A red building with a sign reading "Shaker Mill Inn".

3. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is Rp2.644.655
Rp2.901.187 total
includes taxes & fees
15 Nov - 16 Nov
Shaker Mill Inn
A covered balcony with a table and two white wire chairs, a bowl of fruit, and a glass of juice.

4. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.2 out of 10, Wonderful, (159 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is Rp3.153.389
Rp3.522.336 total
includes taxes & fees
22 Nov - 23 Nov
The Trail in Adams - Berkshires’ Art Hotel
A kitchen with wooden shelves holding mugs and tea boxes, a coffee machine, and a toaster.

5. UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
The price is Rp1.793.484
Rp1.895.712 total
includes taxes & fees
20 Nov - 21 Nov
UU Rowe Camp and Conference Center
Front of property

6. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (110 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is Rp4.205.549
Rp4.932.373 total
includes taxes & fees
15 Nov - 16 Nov
The Inn at Stockbridge
A vintage turquoise Ford truck parked in front of a building labeled "CHAMBÉRY INN."

7. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (390 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is Rp3.840.951
Rp4.290.360 total
includes taxes & fees
13 Dec - 14 Dec
Chambery Inn
A room with wooden paneling, a piano, a chair, and a door leading to another room.

8. South Shire

South Shire
4.0 star property
Bennington
9.0 out of 10, Wonderful, (141 reviews)
"Lovely place. Great room. Nice breakfast. Convenient to nearby restaurants."
United States
Jeffrey
The price is Rp2.738.586
Rp3.183.864 total
includes taxes & fees
16 Nov - 17 Nov
South Shire
A large, two-story house with a covered porch and multiple chimneys.

9. The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.6 out of 10, Exceptional, (291 reviews)
"We enjoyed our stay."
United States
Robert
The price is Rp4.087.359
Rp4.455.221 total
includes taxes & fees
23 Nov - 24 Nov
The Four Chimneys Inn
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

10. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is Rp6.696.981
Rp7.480.473 total
includes taxes & fees
13 Dec - 14 Dec
Devonfield Inn B&B
A dining table with pastries, a coffee pot, and a vase of sunflowers.

11. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (110 reviews)
"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."
United States
Cynthia
The price is Rp4.156.121
Rp4.642.333 total
includes taxes & fees
20 Nov - 21 Nov
Granville House
A snow-covered outdoor area with a patio, seating, and a covered dining area.

12. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,000 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is Rp3.085.621
Rp3.539.208 total
includes taxes & fees
16 Nov - 17 Nov
The Cornell Inn, Lenox & The Berkshires
A two-story house with a brick entrance and a white facade.

13. 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
9.4 out of 10, Exceptional, (121 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is Rp6.965.903
Rp8.426.756 total
includes taxes & fees
28 Nov - 29 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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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Learn more about Ashuwillticook Rail Trail

Venture to sights like Cheshire Reservoir as you discover the local area in Ashuwillticook Rail Trail.

See all hotels in Ashuwillticook Rail Trail
A paved path flanked by trees with autumn foliage, a wooden fence, and a clear blue sky.

Top reviews in Ashuwillticook Rail Trail

A snow-covered outdoor area with a patio, seating, and a covered dining area.
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox

10/10 Excellent

Lovely room, comfortable bed and a nice breakfast.
United Kingdom
judith
Reviewed October 10, 2026
The Cornell Inn, Lenox & The Berkshires