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Check prices for these dates

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul
In one month
24 Jul - 26 Jul
In two months
21 Aug - 23 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, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 647
AED 709 total
includes taxes & fees
1 Jul - 2 Jul
Shaker Mill 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 AED 489
AED 543 total
includes taxes & fees
26 Jun - 27 Jun
Olde Judge Mansion
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 AED 544
AED 604 total
includes taxes & fees
24 Jun - 25 Jun
Gardner Farm Inn
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (108 reviews)
"Very nice hotel."
United States
Erdem
The price is AED 657
AED 736 total
includes taxes & fees
7 Jul - 8 Jul
Inn at Silver Maple Farm
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 AED 753
AED 841 total
includes taxes & fees
30 Jun - 1 Jul
The Trail in Adams - Berkshires’ Art Hotel
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is AED 754
AED 868 total
includes taxes & fees
24 Jun - 25 Jun
The Cornell Inn, Lenox & The Berkshires
Interior

The Morgan State House

The Morgan State House
3.5 star property
Albany
9.2 out of 10, Wonderful, (548 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 AED 600
AED 648 total
includes taxes & fees
5 Jul - 6 Jul
The Morgan State House
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 AED 734
AED 820 total
includes taxes & fees
24 Jun - 25 Jun
Whistler's Inn Bed & Breakfast
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 AED 1,561
AED 1,712 total
includes taxes & fees
29 Jun - 30 Jun
Inn at Kenmore Hall
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (379 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 992
AED 1,108 total
includes taxes & fees
29 Jun - 30 Jun
Chambery Inn
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 AED 1,213
AED 1,467 total
includes taxes & fees
6 Jul - 7 Jul
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
The price is AED 1,327
AED 1,556 total
includes taxes & fees
24 Jun - 25 Jun
The Inn at Stockbridge
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 AED 1,429
AED 1,596 total
includes taxes & fees
24 Jun - 25 Jun
Devonfield Inn B&B
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 AED 2,515
AED 2,809 total
includes taxes & fees
23 Jul - 24 Jul
33 Main
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AED 1,261
AED 1,648 total
includes taxes & fees
24 Jun - 25 Jun
Historic Susan B. Anthony Room - Cozy & Charming Stay
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 AED 863
AED 912 total
includes taxes & fees
7 Jul - 8 Jul
Harbour House Inn
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 1,203
AED 1,572 total
includes taxes & fees
29 Jun - 30 Jun
Experience Timeless Elegance in The Edith Wharton Room!
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 AED 1,320
AED 1,727 total
includes taxes & fees
29 Jun - 30 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 AED 1,408
AED 1,841 total
includes taxes & fees
6 Jul - 7 Jul
Elegant Carriage House room with a queen bed and private patio.
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 AED 1,203
AED 1,572 total
includes taxes & fees
29 Jun - 30 Jun
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"very scenic and well maintained property"
geraldine 4-night trip
Posted less than an hour ago
Vacation Village in the Berkshires

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 Mountain Coaster 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.