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Check prices for these dates

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

Our top choices for Stephentown bed & breakfast

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

1. 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 ￥25,840
￥28,941 total
includes taxes & fees
Dec 2 - Dec 3
Inn at Silver Maple Farm
A red building with a sign reading "Shaker Mill Inn."

2. 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 ￥22,846
￥25,061 total
includes taxes & fees
Nov 4 - Nov 5
Shaker Mill 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.

3. 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 ￥24,122
￥26,944 total
includes taxes & fees
Nov 8 - Nov 9
The Trail in Adams - Berkshires’ Art Hotel
A snow-covered outdoor area with a patio, seating, and a covered dining area.

4. 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 ￥26,788
￥30,727 total
includes taxes & fees
Nov 4 - Nov 5
The Cornell Inn, Lenox & The Berkshires
A traditional living room with a fireplace, patterned rugs, and a bookshelf.

5. 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 ￥15,887
￥17,747 total
includes taxes & fees
Nov 8 - Nov 9
Whistler's Inn Bed & Breakfast
A garden with a stone wall, various plants, and a small shed.

6. Gardner Farm Inn

Gardner Farm Inn
3.5 star property
Troy
10.0 out of 10, Exceptional, (225 reviews)
"We really enjoyed our stay. The host is very personable and the breakfast was delicious. The house is on a busy road but there is an accessible patch of woods."
United States
Karon
The price is ￥26,786
￥29,733 total
includes taxes & fees
Nov 18 - Nov 19
Gardner Farm Inn
A historic building with a wooden door, two wreaths, and a sign that reads "Old Judge Mansion."

7. Olde Judge Mansion

Olde Judge Mansion
2.0 star property
Troy
8.8 out of 10, Excellent, (258 reviews)
"The facility was unique and the owner very helpful and friendly. She provided a great breakfast! My only concern was the sketchy looking neighborhood with teenagers (?) running and yelling on the corner. It was quiet past 10 pm and my car was safe in the parking lot."
United States
Sallie
The price is ￥20,813
￥23,102 total
includes taxes & fees
Nov 23 - Nov 24
Olde Judge Mansion
A two-story building with a sign reading "Chambéry Inn".

8. 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 ￥28,928
￥32,313 total
includes taxes & fees
Nov 10 - Nov 11
Chambery Inn
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 ￥42,185
￥49,477 total
includes taxes & fees
Nov 8 - Nov 9
The Inn at Stockbridge
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

10. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is ￥42,851
￥53,382 total
includes taxes & fees
Nov 4 - Nov 5
Experience Timeless Elegance in The Edith Wharton Room!
A patio with a curved sofa, two potted plants, and a table.

11. The Morgan State House

The Morgan State House
3.5 star property
Albany
9.2 out of 10, Wonderful, (570 reviews)
"Great place to stay"
United States
Michael
The price is ￥43,588
￥47,076 total
includes taxes & fees
Nov 8 - Nov 9
The Morgan State House
A two-story house with a brick entrance and a white facade.

12. 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 ￥60,302
￥72,949 total
includes taxes & fees
Nov 26 - Nov 27
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A large, two-story house with a well-maintained lawn and a fence.

13. 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 ￥58,261
￥65,077 total
includes taxes & fees
Nov 4 - Nov 5
Devonfield Inn B&B
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

14. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.6 out of 10, Exceptional, (178 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is ￥26,148
￥30,471 total
includes taxes & fees
Dec 1 - Dec 2
Brook Farm Inn
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is ￥42,851
￥53,382 total
includes taxes & fees
Nov 4 - Nov 5
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

16. Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is ￥50,430
￥62,428 total
includes taxes & fees
Nov 5 - Nov 6
Historic Susan B. Anthony Room - Cozy & Charming Stay
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.

17. 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 ￥45,378
￥56,103 total
includes taxes & fees
Nov 4 - Nov 5
Elegant Carriage House room with a queen bed and private patio.
A porch with a white railing, a potted plant, and a view of a garden.

18. 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 ￥47,904
￥59,354 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Carriage House room with a double bed and private balcony
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

19. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
The price is ￥61,798
￥76,878 total
includes taxes & fees
Nov 8 - Nov 9
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
A bedroom with a bed, a television, a fireplace, and a window.

20. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is ￥66,851
￥80,668 total
includes taxes & fees
Nov 8 - Nov 9
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Very nice place beautiful view"
Brian 1-night trip
Posted 1 hour ago
Berkshires Untold

Find out more about Stephentown

Stephentown B&B information

Number of reviews
2,080
Accommodation
36 B&B
Lowest Price
￥17,747
Highest Price
￥80,668

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, Zema's Nursery and Taconic Ridge State Forest 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: Berkshire Mountain House: 7 rooms. 2.4 mi (3.9 km) from the heart of Stephentown. Enjoy the free buffet breakfast and rooftop terrace. The Cornell Inn, Lenox & The Berkshires: 14.2 mi (22.8 km) from the downtown core. Enjoy the free full breakfast and unique décor. Inn at Silver Maple Farm: 11 rooms. 10 mi (16.1 km) from the heart of downtown. Enjoy the free buffet breakfast and designer toiletries. Shaker Mill Inn: 9 rooms. Located 15.2 mi (24.4 km) from the core of Stephentown.
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 Zema's Nursery and Taconic Ridge State Forest. 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.

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