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
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept
In one month
25 Sept - 27 Sept
In two months
23 Oct - 25 Oct

Our top choices for Ashuwillticook Rail Trail bed & breakfast

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (56 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is S$310
includes taxes & fees
31 Aug - 1 Sept
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
9.0 out of 10, Wonderful, (154 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is S$280
includes taxes & fees
31 Aug - 1 Sept
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, (470 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is S$228
includes taxes & fees
9 Sept - 10 Sept
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, (114 reviews)
"Very nice hotel."
United States
Erdem
The price is S$169
includes taxes & fees
31 Aug - 1 Sept
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, (516 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is S$226
includes taxes & fees
20 Sept - 21 Sept
Whistler's Inn Bed & Breakfast
A two-story building with a sign reading "Chambéry Inn".

6. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (386 reviews)
"The room was clean and very quiet. Breakfast was delivered to our room as requested."
United States
Richard
The price is S$383
includes taxes & fees
22 Sept - 23 Sept
Chambery Inn

7. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (104 reviews)
"Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another stay when we’re in the area."
United Kingdom
Michele
The price is S$562
includes taxes & fees
14 Sept - 15 Sept
The Inn at Stockbridge
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
9.2 out of 10, Wonderful, (131 reviews)
"Super charming Victorian home. Perfect spot to disconnect and enjoy a restful stay"
United States
Maria Belinda
The price is S$301
includes taxes & fees
31 Aug - 1 Sept
South Shire
A large, two-story house with a well-maintained lawn and a fence.

9. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Excellent food and helpful staff"
United States
Richard
The price is S$552
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B
A two-story house with a brick entrance and a white facade.

10. 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, (116 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is S$508
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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
9.2 out of 10, Wonderful, (1,001 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is S$288
includes taxes & fees
31 Aug - 1 Sept
The Cornell Inn, Lenox & The Berkshires
A dining table with pastries, a coffee pot, and a vase of sunflowers.

12. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (105 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 S$390
includes taxes & fees
3 Sept - 4 Sept
Granville House
A bedroom with a double bed, two chairs, a small table with a hat, and floral curtains.

13. The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (290 reviews)
"Peaceful and whimsical stay in a historic inn. The breakfast was delicious (served with the best local maple syrup) and location was a 5 minute drive to the downtown area."
United States
Jeane
The price is S$394
includes taxes & fees
31 Aug - 1 Sept
The Four Chimneys Inn
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

Find out more about Ashuwillticook Rail Trail

Ashuwillticook Rail Trail B&B information

Number of reviews
2,582
Accommodation
0 B&B
Lowest Price
S$169
Highest Price
S$562

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