Bed and Breakfast in Stephentown

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Stephentown bed & breakfast

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

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 NZ$331
includes taxes & fees
3 Dec - 4 Dec
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 NZ$287
includes taxes & fees
12 Nov - 13 Nov
Shaker Mill Inn
A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

3. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.8 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is NZ$471
includes taxes & fees
9 Dec - 10 Dec
Harbour House Inn
A garden with a white gazebo, a brick pathway, and various plants and flowers.

4. 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
Whistler's Inn 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.

5. 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 NZ$344
includes taxes & fees
30 Nov - 1 Dec
The Trail in Adams - Berkshires’ Art Hotel
Front of property

6. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (110 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is NZ$514
includes taxes & fees
15 Nov - 16 Nov
The Inn at Stockbridge
A garden with a stone wall, various plants, and a small shed.

7. 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 NZ$334
includes taxes & fees
24 Nov - 25 Nov
Gardner Farm Inn
A historic building with a wooden door, two wreaths, and a sign that reads "Old Judge Mansion."

8. 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 NZ$271
includes taxes & fees
24 Nov - 25 Nov
Olde Judge Mansion
A two-story building with a sign reading "Chambéry Inn".

9. 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 NZ$388
includes taxes & fees
7 Dec - 8 Dec
Chambery Inn
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 NZ$592
includes taxes & fees
15 Nov - 16 Nov
Experience Timeless Elegance in The Edith Wharton Room!
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

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 NZ$732
includes taxes & fees
13 Nov - 14 Nov
Devonfield Inn B&B
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 NZ$820
includes taxes & fees
26 Nov - 27 Nov
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.

13. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,003 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is NZ$352
includes taxes & fees
11 Nov - 12 Nov
The Cornell Inn, Lenox & The Berkshires
A dining table with a view of trees and parked cars through a window with wooden shutters.

14. 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 NZ$520
includes taxes & fees
20 Nov - 21 Nov
The Morgan State House
A porch with a white railing, a potted plant, and a view of a garden.

15. 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 NZ$653
includes taxes & fees
15 Nov - 16 Nov
Cozy Carriage House room with a double bed and private balcony
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.

16. 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 NZ$627
includes taxes & fees
15 Nov - 16 Nov
Elegant Carriage House room with a queen bed and private patio.
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is NZ$592
includes taxes & fees
11 Nov - 12 Nov
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.

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is NZ$688
includes taxes & fees
11 Nov - 12 Nov
Historic Susan B. Anthony Room - Cozy & Charming Stay
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 NZ$842
includes taxes & fees
12 Nov - 13 Nov
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 NZ$922
includes taxes & fees
12 Nov - 13 Nov
"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 reviews in Stephentown

A two-story building with a sign reading "Chambéry Inn".
Chambery Inn

Chambery Inn

Chambery Inn
Lee

10/10 Excellent

The room was large and comfortable and had a gas fire. It was also on ground floor so easy access for suitcases. Staff were helpful and pleasant and it is close to lots of restaurants within walking distance.
Australia
Anonymous traveller
Reviewed October 28, 2019
Chambery Inn

Frequently Asked Questions

Searching for B&Bs in Stephentown?

Whether you're on a romantic holiday and are looking to stay somewhere quiet, or you're travelling solo and hoping to get some tips from locals, B&Bs can be a great choice for many travellers. 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 a good option for your stay?

With attentive service, opportunities to meet other guests and of course a full breakfast, B&Bs offer 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 city centre. Enjoy the free full breakfast and unique decor. Inn at Silver Maple Farm: 11 rooms. 10 mi (16.1 km) from the city centre. 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 stay in Stephentown, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stephentown are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

What is there to do in Stephentown?

When you want to see 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?

Mapping out your trip in and around Stephentown is easy 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 a rental car for your journey.