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Search B&B in Ashuwillticook Rail Trail

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Check prices for these dates

Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan
In one month
16 Jan - 18 Jan
In two months
13 Feb - 15 Feb

Our top choices for Ashuwillticook Rail Trail bed & breakfast

Exterior
UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
The price is RM610
RM645 total
includes taxes & fees
18 Dec - 19 Dec
UU Rowe Camp and Conference Center
Exterior
The Engel House

The Engel House

The Engel House
3.0 star property
Jacksonville
9.2 out of 10, Wonderful, (17)
"A very quaint property. The room was comfortable and clean."
United States
Frank
The Engel House
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
The price is RM447
RM490 total
includes taxes & fees
18 Dec - 19 Dec
Shaker Mill Inn
Exterior
Harbour House Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
United States
alton
The price is RM881
RM931 total
includes taxes & fees
7 Jan - 8 Jan 2026
Harbour House Inn
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel

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, (142)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is RM712
RM795 total
includes taxes & fees
17 Dec - 18 Dec
The Trail in Adams - Berkshires’ Art Hotel
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (89)
"Outstanding all around!"
United States
Jonathan
The price is RM819
RM914 total
includes taxes & fees
15 Jan - 16 Jan 2026
Granville House
Front of property
The Inn at Stockbridge

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is RM1,028
RM1,205 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Inn at Stockbridge
Front of property
Chambery Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is RM738
RM865 total
includes taxes & fees
19 Dec - 20 Dec
Lakehouse Inn
Front of property – evening/night
Devonfield Inn B&B

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Premium bedding, individually decorated, individually furnished
The Four Chimneys Inn

The Four Chimneys Inn

The Four Chimneys Inn
4.0 star property
Bennington
9.4 out of 10, Exceptional, (280)
"What an absolutely amazing stay!! Everything was perfect. Highly recommend having dinner onsite. "
United States
Jon
The Four Chimneys Inn
View from room
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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is RM1,563
RM1,891 total
includes taxes & fees
14 Jan - 15 Jan 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is RM1,717
RM1,918 total
includes taxes & fees
11 Jan - 12 Jan 2026
33 Main
Exterior
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1002)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is RM684
RM787 total
includes taxes & fees
22 Dec - 23 Dec
The Cornell Inn, Lenox & The Berkshires
Aerial view
Inn at Silver Maple Farm

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
The price is RM529
RM592 total
includes taxes & fees
22 Dec - 23 Dec
Inn at Silver Maple Farm
Premium bedding, iron/ironing board, free WiFi, bed sheets
Tanglewood Suites

Tanglewood Suites

Tanglewood Suites
2.5 star property
Stockbridge
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is RM896
RM896 total
includes taxes & fees
30 Dec - 31 Dec
Tanglewood Suites
Lobby
Inn at Kenmore Hall

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is RM2,353
RM2,582 total
includes taxes & fees
30 Dec - 31 Dec
Inn at Kenmore Hall
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"A magical, magical New England weekend at The Red Lion Inn. The room was so warm, the bed and pillows were so comfortable and just the right firmness. The pool and hot tube were open, maybe bring a swimsuit if you are up for a soak in the hot tub on a cold snowy day or night. Check in was a breeze, staff were warm and welcoming. Highly recommend making reservations at their Tavern or Dining Area. Several small cafes and charming local shops close by for Christmas shopping"
Judith Pauline 1-night trip
Posted 9 hours ago
The Red Lion Inn

Find out more about Ashuwillticook Rail Trail

Ashuwillticook Rail Trail B&B information

Number of reviews
2,670
Accommodation
28 B&B
Lowest Price
RM490
Highest Price
RM2,582

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