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Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

B&B in Stephentown

Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
Adams
8.8 out of 10, Excellent, (141)
"It was clean and quiet good Breakfast "
United States
William
The price is AED 638
AED 713 total
includes taxes & fees
15 Nov - 16 Nov
The Trail in Adams - Berkshires’ Art Hotel
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (435)
"Nice place, easy check in"
United States
Robert
The price is AED 388
AED 426 total
includes taxes & fees
20 Nov - 21 Nov
Shaker Mill Inn
Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (52)
"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 AED 935
AED 988 total
includes taxes & fees
1 Dec - 2 Dec
Harbour House Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"Great Views & Hospitality"
United States
Gerald
The price is AED 632
AED 741 total
includes taxes & fees
16 Nov - 17 Nov
Lakehouse Inn
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (372)
"We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew which was appreciated. We look forward to coming back"
United States
Samuel
Chambery Inn
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
"A first class little inn"
United States
Philip
The price is AED 921
AED 1,080 total
includes taxes & fees
20 Nov - 21 Nov
The Inn at Stockbridge
Property grounds
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 star property
Lenox
7.8 out of 10, Good, (500)
"We had a wonderful stay. We are so glad we chose this inn. The location is superb…a five-minute walk to the center of Lenox! It is a beautiful inn with a lot of charm, and the staff is warm and friendly. We loved our large room too! Definitely plan on staying here again when we come back to the area! "
United States
Itzhak
The price is AED 497
AED 555 total
includes taxes & fees
15 Nov - 16 Nov
Whistler's Inn Bed & Breakfast
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 AED 1,460
AED 1,631 total
includes taxes & fees
23 Nov - 24 Nov
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 AED 768
AED 1,124 total
includes taxes & fees
16 Nov - 17 Nov
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi
Tanglewood Suites

Tanglewood Suites

2.5 star property
Stockbridge
6.4 out of 10, (22)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
United States
Amanda
The price is AED 804
AED 804 total
includes taxes & fees
1 Dec - 2 Dec
Tanglewood Suites
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
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)
"It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!"
United States
Carol Anne
The price is AED 1,403
AED 1,697 total
includes taxes & fees
30 Nov - 1 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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, (1002)
"Very friendly staff. "
United States
Pamela
The price is AED 473
AED 672 total
includes taxes & fees
16 Nov - 17 Nov
The Cornell Inn, Lenox & The Berkshires
Aerial view
Inn at Silver Maple Farm

Inn at Silver Maple Farm

3.0 star property
East Chatham
9.8 out of 10, Exceptional, (97)
"This was the perfect spot for a Tanglewood night..beautiful, charming, great staff and delicious breakfast..."
United States
Jane
The price is AED 474
AED 531 total
includes taxes & fees
23 Nov - 24 Nov
Inn at Silver Maple Farm
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 AED 826
AED 1,198 total
includes taxes & fees
17 Nov - 18 Nov
Elegant Carriage House room with a queen bed and private patio.
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 AED 768
AED 1,124 total
includes taxes & fees
16 Nov - 17 Nov
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 AED 885
AED 1,276 total
includes taxes & fees
17 Nov - 18 Nov
Cozy Carriage House room with a double bed and private balcony
Terrace/patio
Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox
The price is AED 944
AED 1,350 total
includes taxes & fees
16 Nov - 17 Nov
Historic Susan B. Anthony Room - Cozy & Charming Stay
Fireplace
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 AED 1,208
AED 1,686 total
includes taxes & fees
16 Nov - 17 Nov
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
1 bedroom, bed sheets
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Lenox
The price is AED 1,326
AED 1,838 total
includes taxes & fees
16 Nov - 17 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 Stephentown Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"The room was clean and the staff was also considerate. "
Suman 1-night trip
Posted 15 hours ago
Comfort Inn & Suites East Greenbush - Albany

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. Shaker Mill Inn: 9 rooms. Situated 15.2 mi (24.4 km) from the heart of Stephentown. Chambery Inn: 9 rooms. 18.4 mi (29.7 km) from the heart of downtown. Enjoy the private yard 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 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.