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Our top choices for Stephentown bed & breakfast

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (453 reviews)
"Everything was excellent"
United States
Barbara
The price is AED 383
AED 420 total
includes taxes & fees
13 May - 14 May
Shaker Mill Inn

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, (146 reviews)
"Great little Inn with a well equipped kitchen, clean rooms, and art books. It made for a lovely base for our two day Berkshires adventure."
United States
selmin
The price is AED 638
AED 713 total
includes taxes & fees
10 May - 11 May
The Trail in Adams - Berkshires’ Art Hotel

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is AED 918
AED 970 total
includes taxes & fees
11 May - 12 May
Harbour House Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is AED 628
AED 702 total
includes taxes & fees
10 May - 11 May
Chambery Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is AED 988
AED 1,104 total
includes taxes & fees
19 May - 20 May
Devonfield Inn B&B

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is AED 965
AED 1,132 total
includes taxes & fees
21 May - 22 May
The Inn at Stockbridge

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is AED 939
AED 1,049 total
includes taxes & fees
25 May - 26 May
Whistler's Inn Bed & Breakfast

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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is AED 1,137
AED 1,375 total
includes taxes & fees
25 May - 26 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (28 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is AED 1,561
AED 1,712 total
includes taxes & fees
10 May - 11 May
Inn at Kenmore Hall

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (105 reviews)
"Very nice hotel."
United States
Erdem
The price is AED 584
AED 654 total
includes taxes & fees
4 Jun - 5 Jun
Inn at Silver Maple Farm

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AED 2,399
AED 2,679 total
includes taxes & fees
14 May - 15 May
33 Main

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AED 791
AED 1,035 total
includes taxes & fees
13 May - 14 May
Experience Timeless Elegance in The Edith Wharton Room!

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Delicious breakfast and beautiful room!"
United States
Laarni
The price is AED 475
AED 546 total
includes taxes & fees
12 May - 13 May
The Cornell Inn, Lenox & The Berkshires

Olde Judge Mansion

Olde Judge Mansion
2.0 star property
Troy
8.8 out of 10, Excellent, (246 reviews)
"Breakfast was fabulous! The Mansion is cozy and owner Tina so helpful and knowledgeable. I really enjoyed my stay. The place is a gem."
United States
Joan
The price is AED 515
AED 572 total
includes taxes & fees
10 May - 11 May
Olde Judge Mansion

Gardner Farm Inn

Gardner Farm Inn
3.5 star property
Troy
10.0 out of 10, Exceptional, (207 reviews)
"Great host Very welcoming. Going to Troy stay here. Really nice"
United States
John
The price is AED 526
AED 584 total
includes taxes & fees
11 May - 12 May
Gardner Farm Inn

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 1,026
AED 1,337 total
includes taxes & fees
13 May - 14 May
Cozy Carriage House room with a double bed and private balcony

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 1,026
AED 1,333 total
includes taxes & fees
19 May - 20 May
Elegant Carriage House room with a queen bed and private patio.

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 791
AED 1,031 total
includes taxes & fees
10 May - 11 May
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AED 1,085
AED 1,413 total
includes taxes & fees
10 May - 11 May
Historic Susan B. Anthony Room - Cozy & Charming Stay

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AED 1,467
AED 1,860 total
includes taxes & fees
11 May - 12 May
"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

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. Located 18.4 mi (29.7 km) from the core of Stephentown. 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 Mount Lebanon 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.