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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

B&B in Stephentown

Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is SAR 376
SAR 413 total
includes taxes & fees
8 Dec - 9 Dec
Shaker Mill Inn
Terrace/patio
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 SAR 652
SAR 728 total
includes taxes & fees
2 Dec - 3 Dec
The Trail in Adams - Berkshires’ Art Hotel
Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is SAR 896
SAR 947 total
includes taxes & fees
8 Dec - 9 Dec
Harbour House Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is SAR 677
SAR 793 total
includes taxes & fees
4 Dec - 5 Dec
Lakehouse Inn
Front of property
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
Exterior
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 SAR 1,031
SAR 1,209 total
includes taxes & fees
24 Dec - 25 Dec
The Inn at Stockbridge
Front of property - evening/night
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
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets
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 SAR 822
SAR 822 total
includes taxes & fees
2 Dec - 3 Dec
Tanglewood Suites
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
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 SAR 1,599
SAR 1,787 total
includes taxes & fees
29 Dec - 30 Dec
33 Main
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

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

Lenox
The price is SAR 853
SAR 1,238 total
includes taxes & fees
21 Dec - 22 Dec
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lobby
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 SAR 1,594
SAR 1,749 total
includes taxes & fees
14 Dec - 15 Dec
Inn at Kenmore Hall
Aerial view
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 SAR 597
SAR 668 total
includes taxes & fees
2 Dec - 3 Dec
Inn at Silver Maple Farm
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1004)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is SAR 531
SAR 740 total
includes taxes & fees
21 Dec - 22 Dec
The Cornell Inn, Lenox & The Berkshires
Business center
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 SAR 1,433
SAR 1,733 total
includes taxes & fees
14 Dec - 15 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!

Lenox
The price is SAR 853
SAR 1,238 total
includes taxes & fees
21 Dec - 22 Dec
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets
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 SAR 980
SAR 1,401 total
includes taxes & fees
21 Dec - 22 Dec
Cozy Carriage House room with a double bed and private balcony
1 bedroom, WiFi, bed sheets
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 SAR 1,108
SAR 1,535 total
includes taxes & fees
1 Jan - 2 January 2026
Elegant Carriage House room with a queen bed and private patio.
Property grounds
Gardner Farm Inn

Gardner Farm Inn

3.5 star property
Troy
10.0 out of 10, Exceptional, (199)
"John was an incredibly welcoming host. He provided helpful recommendations for local attractions along with a great breakfast! The B&B has a great deal of character and charm."
United States
Benito
The price is SAR 597
SAR 663 total
includes taxes & fees
4 Dec - 5 Dec
Gardner Farm Inn
Terrace/patio
Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox
The price is SAR 1,044
SAR 1,481 total
includes taxes & fees
21 Dec - 22 Dec
Historic Susan B. Anthony Room - Cozy & Charming Stay
Property entrance
Olde Judge Mansion

Olde Judge Mansion

2.0 star property
Troy
8.8 out of 10, Excellent, (246)
"Cozy, old fashioned mansion, well maintained and comfortable. Easy off street parking. Owner, Tina, supplied ample information about check-in and local dining. "
United States
Donald
The price is SAR 474
SAR 526 total
includes taxes & fees
9 Dec - 10 Dec
Olde Judge Mansion
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 Stephentown Hotel Reviews

Courtyard by Marriott Albany Troy/Waterfront

Courtyard by Marriott Albany Troy/Waterfront

10/10 Excellent
"Convenient location for our travels. Lovely view of the river. Close to restaurants. Kind staff"
Ruth 1-night trip
Posted 1 day ago
Courtyard by Marriott Albany Troy/Waterfront

Frequently asked questions

Searching for B&Bs in Stephentown?
Whether you're on a family vacation and want a small, cozy place to stay, or you're traveling solo and hoping to meet fellow tourists, B&Bs can be a great choice for many travelers. When you want to explore some attractions in town, Taconic Ridge State Forest and Zema's Nursery are worth a stop.
How do you know if a B&B is the right choice for your stay?
With attentive service, opportunities to socialize with other guests, and delectable breakfasts, B&Bs provide a truly one-of-a-kind setting.
What are the best bed and breakfasts in Stephentown?
Here are some well-liked B&Bs in the area: The Cornell Inn, Lenox & The Berkshires: 14.2 mi (22.8 km) from the heart of Stephentown. Enjoy the free full breakfast and unique décor. Chambery Inn: 9 rooms. Situated 18.4 mi (29.7 km) from the heart of Stephentown. Enjoy the private yard and deli. Shaker Mill Inn: 9 rooms. 15.2 mi (24.4 km) from the heart of downtown.Lakehouse Inn: 14 rooms. Located 17.1 mi (27.6 km) from the core of Stephentown. Enjoy the free full breakfast and deli.
What's the best time of year to book my B&B in Stephentown?
When you're dreaming of a trip to Stephentown, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Stephentown are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Stephentown?
When you want to check out some attractions in town, you might consider a visit to Taconic Ridge State Forest and Zema's Nursery. Jiminy Peak Mountain Resort and Hancock Shaker Village are also some sites to visit if you want to see more of the area.
How can I get to and around Stephentown?
You can plan your excursions in and around Stephentown ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 10.3 mi (16.6 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 24.2 mi (38.9 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.