Find the Best Stephentown Bed and Breakfast

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 Jun - 14 Jun
In two weeks
19 Jun - 21 Jun
In one month
3 Jul - 5 Jul
In two months
31 Jul - 2 Aug

Our top choices for Stephentown bed & breakfast

Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (457 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is £112
includes taxes & fees
2 Jun - 3 Jun
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, (151 reviews)
"Incredible staff, free parking and cute rooms!"
Canada
Priscilla
The price is £148
includes taxes & fees
3 Jun - 4 Jun
The Trail in Adams - Berkshires’ Art Hotel
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (377 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 £142
includes taxes & fees
2 Jun - 3 Jun
Chambery Inn
Exterior

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)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is £129
includes taxes & fees
9 Jun - 10 Jun
The Cornell Inn, Lenox & The Berkshires
Front of property – evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is £273
includes taxes & fees
4 Jun - 5 Jun
Devonfield Inn B&B
Property grounds

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 £221
includes taxes & fees
7 Jun - 8 Jun
Whistler's Inn Bed & Breakfast
Suite, Private Bathroom (RedBird Suite) | View from room

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 £297
includes taxes & fees
14 Jun - 15 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (107 reviews)
"Very nice hotel."
United States
Erdem
The price is £132
includes taxes & fees
4 Jun - 5 Jun
Inn at Silver Maple Farm
Lobby

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 £347
includes taxes & fees
16 Jun - 17 Jun
Inn at Kenmore Hall
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 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is £487
includes taxes & fees
2 Jun - 3 Jun
33 Main
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 £241
includes taxes & fees
9 Jun - 10 Jun
Experience Timeless Elegance in The Edith Wharton Room!
Property grounds

Gardner Farm Inn

Gardner Farm Inn
3.5 star property
Troy
10.0 out of 10, Exceptional, (209 reviews)
"The house was beautiful, the breakfast was delicious, and John was a kind and gracious host. It was like staying with an old friend. Highly recommend."
United States
Karen
The price is £120
includes taxes & fees
2 Jun - 3 Jun
Gardner Farm Inn
Property entrance

Olde Judge Mansion

Olde Judge Mansion
2.0 star property
Troy
8.8 out of 10, Excellent, (247 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 £116
includes taxes & fees
3 Jun - 4 Jun
Olde Judge Mansion
Exterior

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 £183
includes taxes & fees
2 Jun - 3 Jun
Harbour House Inn
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is £333
includes taxes & fees
2 Jun - 3 Jun
Historic Susan B. Anthony Room - Cozy & Charming Stay
Shower, towels

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is £239
includes taxes & fees
7 Jun - 8 Jun
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

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 £317
includes taxes & fees
4 Jun - 5 Jun
Cozy Carriage House room with a double bed and private balcony
Interior

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 £302
includes taxes & fees
14 Jun - 15 Jun
Elegant Carriage House room with a queen bed and private patio.
Interior

The Morgan State House

The Morgan State House
3.5 star property
Albany
9.2 out of 10, Wonderful, (545 reviews)
"Beautiful brownstone with welcoming staff/owners. My accommodation was in the condo nearby with a beauty bedroom, sitting area and small kitchen. Great location with easy access to the State Capitol and nearby restaurants. Across from the park too, which is lovely. This is a great place to stay in Albany."
United States
Claire B
The price is £125
includes taxes & fees
4 Jun - 5 Jun
The Morgan State House
Shower, towels

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is £419
includes taxes & fees
2 Jun - 3 Jun
"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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stephentown Hotel Reviews

Berkshires Untold

Berkshires Untold

4/10 Poor
"From the time we showed up and told that they had no reservation for us, when we paid in full for a king suite, until we left, this experience was frustrating and full of problems. All king suites were sold out, including the one we paid for! We were told we would receive a 50% credit back to our credit card and we have yet to see that. The coffee was either unavailable/self serve or pretty bad. We experienced all of these. The check in person was somewhat helpful but was limited as to what we/they could do to remedy the whole situation. Communications from the upper management have gone unanswered The room we were given instead was very small, no amenities as stated in our reservation, etc I could go on with the sub par remedies, lack of communication and any follow through. Ingress and egress from this hotel is extremely difficult and dangerous, coming from the main four lane highway with no lights. The whole experience was Not pleasant at all on a trip that was a milestone for us. We will not be returning"
AW 2-night trip
Posted 2 hours ago
Berkshires Untold

Find out more about Stephentown

Stephentown B&B information

Number of reviews
3,359
Accommodation
36 B&B
Lowest Price
£112
Highest Price
£487

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. 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 garden and snack bar/deli.
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 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?
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.

Explore a world of travel with Expedia