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
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct
In one month
6 Nov - 8 Nov
In two months
4 Dec - 6 Dec

Our top choices for Ashuwillticook Rail Trail bed & breakfast

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.

1. The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (157 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is AED 632
AED 706 total
includes taxes & fees
6 Nov - 7 Nov
The Trail in Adams - Berkshires’ Art Hotel
A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

2. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.6 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is AED 932
AED 985 total
includes taxes & fees
22 Oct - 23 Oct
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, (476 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 507
AED 556 total
includes taxes & fees
1 Nov - 2 Nov
Shaker Mill Inn
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

4. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (117 reviews)
"Very nice hotel."
United States
Erdem
The price is AED 713
AED 798 total
includes taxes & fees
4 Nov - 5 Nov
Inn at Silver Maple Farm
A garden with a white gazebo, a brick pathway, and various plants and flowers.

5. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (519 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is AED 588
AED 657 total
includes taxes & fees
7 Oct - 8 Oct
Whistler's Inn Bed & Breakfast
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

6. The Red Door B&B

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveler
The price is AED 645
AED 1,028 total
includes taxes & fees
26 Oct - 27 Oct
The Red Door B&B
A house with a chimney, surrounded by trees with autumn foliage.

7. 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 493
AED 521 total
includes taxes & fees
24 Oct - 25 Oct
UU Rowe Camp and Conference Center
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, (136 reviews)
"Probably the best and most romantic place in Bennington"
United States
Jorge
The price is AED 715
AED 819 total
includes taxes & fees
30 Oct - 31 Oct
South Shire
A bedroom with a double bed, two chairs, a small table with a hat, and floral curtains.

9. The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (291 reviews)
"Great place! Gorgeous decor!"
United States
Karen
The price is AED 869
AED 947 total
includes taxes & fees
1 Nov - 2 Nov
The Four Chimneys Inn
A two-story building with a sign reading "Chambéry Inn".

10. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (388 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 992
AED 1,108 total
includes taxes & fees
19 Oct - 20 Oct
Chambery Inn
A large, two-story house with a well-maintained lawn and a fence.

11. 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
2 Nov - 3 Nov
Devonfield Inn B&B
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
9.2 out of 10, Wonderful, (1,002 reviews)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
The price is AED 564
AED 647 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
Front of property

13. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (107 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
The price is AED 1,340
AED 1,571 total
includes taxes & fees
1 Nov - 2 Nov
The Inn at Stockbridge
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
9.2 out of 10, Wonderful, (119 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AED 1,234
AED 1,493 total
includes taxes & fees
6 Nov - 7 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A dining table with pastries, a coffee pot, and a vase of sunflowers.

15. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (106 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is AED 933
AED 1,042 total
includes taxes & fees
7 Oct - 8 Oct
Granville House
Room

16. 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, (2 reviews)
"The piano, large spaces, and fireplace were all much appreciated."
United States
Benjamin B.
The price is AED 477
AED 555 total
includes taxes & fees
7 Oct - 8 Oct
Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

17. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AED 909
AED 1,190 total
includes taxes & fees
27 Oct - 28 Oct
Experience Timeless Elegance in The Edith Wharton Room!
Room

18. Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
The price is AED 477
AED 555 total
includes taxes & fees
7 Oct - 8 Oct
Cozy Retreat in historic Farmhouse - Tranquility Room
Room

19. Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
The price is AED 331
AED 408 total
includes taxes & fees
7 Oct - 8 Oct
Cozy Farmhouse Retreat - Ram Dass Room
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

20. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is AED 909
AED 1,190 total
includes taxes & fees
27 Oct - 28 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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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