A paved path flanked by trees with autumn foliage, a wooden fence, and a clear blue sky.

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Ashuwillticook Rail Trail bed & breakfast

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

1. 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 AED 876
AED 926 total
includes taxes & fees
12 Nov - 13 Nov
Harbour House Inn
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

2. 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 AED 630
AED 704 total
includes taxes & fees
6 Dec - 7 Dec
The Trail in Adams - Berkshires’ Art Hotel
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 AED 533
AED 584 total
includes taxes & fees
8 Nov - 9 Nov
Shaker Mill Inn
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

4. 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 AED 602
AED 675 total
includes taxes & fees
2 Dec - 3 Dec
Inn at Silver Maple Farm
A house with a chimney, surrounded by trees with autumn foliage.

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 AED 363
AED 384 total
includes taxes & fees
8 Nov - 9 Nov
UU Rowe Camp and Conference Center
A garden with a white gazebo, a brick pathway, and various plants and flowers.

6. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.2 out of 10, Very good, (522 reviews)
"Delightful experience in a gilded age setting."
United States
George
The price is AED 506
AED 565 total
includes taxes & fees
6 Nov - 7 Nov
Whistler's Inn Bed & Breakfast
A crowded outdoor event with tents and people gathered in a grassy area.

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 AED 681
AED 760 total
includes taxes & fees
10 Nov - 11 Nov
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, (140 reviews)
"Lovely place. Great room. Nice breakfast. Convenient to nearby restaurants."
United States
Jeffrey
The price is AED 585
AED 678 total
includes taxes & fees
21 Nov - 22 Nov
South Shire
Front of property

9. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is AED 981
AED 1,151 total
includes taxes & fees
8 Nov - 9 Nov
The Inn at Stockbridge
Room

10. Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm

Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
Rowe
10.0 out of 10, Exceptional, (3 reviews)
"Great space."
United States
Andrew S.
The price is AED 477
AED 524 total
includes taxes & fees
6 Nov - 7 Nov
Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
A snow-covered outdoor area with a patio, seating, and a covered dining area.

11. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,001 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is AED 624
AED 716 total
includes taxes & fees
9 Nov - 10 Nov
The Cornell Inn, Lenox & The Berkshires
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

12. 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 AED 1,355
AED 1,514 total
includes taxes & fees
13 Nov - 14 Nov
Devonfield Inn B&B
A large, two-story house with a covered porch and multiple chimneys.

13. 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 AED 823
AED 897 total
includes taxes & fees
23 Nov - 24 Nov
The Four Chimneys Inn
A two-story house with a brick entrance and a white facade.

14. 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, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AED 1,333
AED 1,612 total
includes taxes & fees
6 Dec - 7 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A dining area with a round table and four chairs, a radiator, and a window with a view of greenery.

15. 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 AED 937
AED 1,046 total
includes taxes & fees
18 Nov - 19 Nov
Granville House
A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

16. Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is AED 1,147
AED 1,426 total
includes taxes & fees
6 Dec - 7 Dec
Elegant Carriage House room with a queen bed and private patio.
Room

17. Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
The price is AED 331
AED 377 total
includes taxes & fees
6 Nov - 7 Nov
Cozy Farmhouse Retreat - Ram Dass Room
Room

18. Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
The price is AED 477
AED 524 total
includes taxes & fees
6 Nov - 7 Nov
Cozy Retreat in historic Farmhouse - Tranquility Room
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

19. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AED 1,085
AED 1,351 total
includes taxes & fees
6 Dec - 7 Dec
Experience Timeless Elegance in The Edith Wharton Room!
A porch with a white railing, a potted plant, and a view of a garden.

20. Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is AED 1,210
AED 1,506 total
includes taxes & fees
6 Dec - 7 Dec
Cozy Carriage House room with a double bed and private balcony
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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Top Ashuwillticook Rail Trail Hotel Reviews

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