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Compare 31 B&B in Stephentown with updated reviews, rates, and availability.

The Cornell Inn, Lenox
Exterior
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1005)
"What a joy this BnB is. Everything is so lovely, from the staff to the overall facilities. It was a true pleasure to stay here. We will be back for sure. "
The price is SAR 507
SAR 594 total
includes taxes & fees
24 Sep - 25 Sep
The Cornell Inn, Lenox
Lakehouse Inn
Lake
Lakehouse Inn
4.0 star property
9.8 out of 10, Exceptional, (201)
"Came here for an anniversary getaway and had a great time. Property was beautiful room was fantastic staff were great and caring. We checked in and received a bottle of Prosecco from the Inn. Will definitely come back again."
The price is SAR 563
SAR 660 total
includes taxes & fees
29 Sep - 30 Sep
Lakehouse Inn
The Morgan State House
Outdoor dining
The Morgan State House
3.5 star property
9.2 out of 10, Wonderful, (473)
"Great place to stay the host were very friendly and helpful. Rooms were clean great location."
The price is SAR 619
SAR 669 total
includes taxes & fees
2 Oct - 3 Oct
The Morgan State House
Whistler's Inn Bed & Breakfast
Interior
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (456)
"Old fashioned gilded age charm and elegance. Personal attention"
The price is SAR 557
SAR 694 total
includes taxes & fees
25 Sep - 26 Sep
Whistler's Inn Bed & Breakfast
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (117)
"Interior was fine. Area did not seem safe to me. The bathroom looks nice but not very functional. "
The price is SAR 680
SAR 760 total
includes taxes & fees
24 Sep - 25 Sep
The Trail in Adams - Berkshires’ Art Hotel
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (146)
"Very charming inn. The staff was very friendly and helpful."
Brook Farm Inn
Gardner Farm Inn
Room
Gardner Farm Inn
3.5 star property
10.0 out of 10, Exceptional, (162)
"Our first stay at a B&B far exceeded our expectations with John at the Gardner Farm Inn. Breakfast was excellent, the house and decor felt very homey. I would stay here again if we're ever back in Troy!"
The price is SAR 644
SAR 711 total
includes taxes & fees
7 Oct - 8 Oct
Gardner Farm Inn
Inn at Silver Maple Farm
Front of property
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (73)
"Host was welcoming and check in process was seamless"
The price is SAR 859
SAR 928 total
includes taxes & fees
21 Oct - 22 Oct
Inn at Silver Maple Farm
Olde Judge Mansion
Property entrance
Olde Judge Mansion
2.0 star property
8.6 out of 10, Excellent, (230)
"The host was very welcoming and made a great breakfast. She runs a very good show."
The price is SAR 526
SAR 582 total
includes taxes & fees
29 Sep - 30 Sep
Olde Judge Mansion
Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (396)
"Very nice place. Clean and extreme attention to detail which is unusual in a place like this. Will definitely come back. We don't come to the Berkshires to watch TV but we did want to watch the college football game late Sat night. The TV in the room is very small but adequate. "
The price is SAR 897
SAR 984 total
includes taxes & fees
24 Sep - 25 Sep
Shaker Mill Inn
Devonfield Inn B&B
Room
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (113)
"Wonderful place for a quiet getaway for a couple of nights. Scenic setting. Delicious breakfasts, helpful owners and staff on site. We'd book again!"
The price is SAR 1,460
SAR 1,631 total
includes taxes & fees
29 Sep - 30 Sep
Devonfield Inn B&B
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (357)
"Nice place to stay in the Berkshires. The house is very quint and the room very comfortable (especially the bed and pillows). While I did not meet Bob until I checked out, they were always available to help via text. I would go back or recommend friends to stay there."
The price is SAR 1,126
SAR 1,257 total
includes taxes & fees
24 Sep - 25 Sep
Chambery Inn
Harbour House Inn
Room
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is SAR 928
SAR 981 total
includes taxes & fees
24 Sep - 25 Sep
Harbour House Inn
33 Main
Room
33 Main
4.0 star property
10.0 out of 10, Exceptional, (67)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is SAR 2,297
SAR 2,565 total
includes taxes & fees
21 Oct - 22 Oct
33 Main
The Inn at Stockbridge
Exterior
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (95)
"Well-run and elegant property. "
The Inn at Stockbridge
Inn at Kenmore Hall
Front of property
Inn at Kenmore Hall
3.0 star property
10.0 out of 10, Exceptional, (26)
"This is a beautiful property straight out of a magazine. Service was impeccable"
Inn at Kenmore Hall
Tanglewood Suites
Property grounds
Tanglewood Suites
2.5 star property
8.0 out of 10, Very Good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
Tanglewood Suites
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
View from room
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (103)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is SAR 1,722
SAR 2,083 total
includes taxes & fees
24 Sep - 25 Sep
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Room
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
The price is SAR 1,122
SAR 1,434 total
includes taxes & fees
24 Sep - 25 Sep
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Bathroom
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
2.0 out of 10, (1)
"Never even met the inn keepers...no one is in sight...WiFi wouldn’t work...a/c in room would not stay on.....1 item only for breakfast- delivered to room- that has no table or chair- stood in the bathroom to eat!!!! Very expensive for what u get "
The price is SAR 1,122
SAR 1,434 total
includes taxes & fees
24 Sep - 25 Sep
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
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Other property types in Stephentown

Private country home minutes from the Berkshires
Property grounds
Private country home minutes from the Berkshires
5.4 out of 10, (11)
"Do not stay here! I am an international traveler, backpacker, and am used to some rough accommodations, but this stay was truly awful. My friend and I booked the space for a weekend, despite reading the previous reviews, thinking it could not be that bad. The house was overwhelmingly musty, there was mold up into the windowsills, the carpeting felt damp to walk on, and least of all the beds were hard and uncomfortable. We left after one night. It felt like a health hazard to be there. Neither...
The price is SAR 413
SAR 754 total
includes taxes & fees
24 Sep - 25 Sep
Private country home minutes from the Berkshires
The entire Stephentown Hotel! 28 person occupancy
The entire Stephentown Hotel! 28 person occupancy
The entire Stephentown Hotel! 28 person occupancy
Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1714)
"Nice place. Pleasantly surprised how big the suite was. The whole place was very clean from the suite itself, the huge indoor pool and hot tub. The clerk that checked us in was very knowledgeable of the area and just a pleasant person. She is an older lady, I forget her name but she is a definite asset to this property! On the down side the path to the main office was not well lit but we used our flashlights. Also there isn't restaurants on site or groceries available. We had to travel 25...
The price is SAR 633
SAR 732 total
includes taxes & fees
24 Sep - 25 Sep
Vacation Village in the Berkshires
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.

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 of the destination’s attractions, Zema’s Nursery is worth a visit.
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: The Cornell Inn, Lenox: 14.2 mi (22.8 km) from the heart of Stephentown. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. 17.1 mi (27.6 km) from the downtown core. Enjoy the free full breakfast and deli. Brook Farm Inn: 15 rooms. 14.9 mi (24 km) from the heart of downtown. Enjoy the free cooked breakfast and outdoor pool. Gardner Farm Inn: 5 rooms. Located 18.2 mi (29.2 km) from the core of Stephentown. Enjoy the free full breakfast and massage services.
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. Average annual precipitation for Stephentown is 49 inches.
What is there to do in Stephentown?
If you want to check out some popular attractions in Stephentown, you might enjoy a visit to Zema’s Nursery. Jiminy Peak Mountain Resort and Pittsfield State Forest 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.