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Compare 28 B&B in Stephentown with updated reviews, rates, and availability.

The Cornell Inn, Lenox & The Berkshires

3.0 star property
8.8 out of 10, Excellent, (1047)
"What a beautiful, well-appointed room we stayed in at the Cornell! We had "Jennifer's Room" and loved the decor and comfort of the space, including fireplace!! The breakfast was delicious and the staff was super friendly. We'll definitely be back!! "
The price is AED 357
AED 543 total
includes taxes & fees
11 Apr - 12 Apr
The Cornell Inn, Lenox & The Berkshires

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (252)
"Wonderful Location"
Lakehouse Inn

The Morgan State House

3.5 star property
9.2 out of 10, Wonderful, (503)
"It was a great stay - extremely courteous and accommodating. Excellent amenities. I will certainly be coming back. "
The price is AED 644
AED 696 total
includes taxes & fees
17 Apr - 18 Apr
The Morgan State House

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (408)
"Beautiful room, very clean. breakfast was not what i was expecting, walk way from parking lot covered with ice and snow, very dangerous to walk, needs to be cleaned or at least put some salt on the ground. other then that everything was excellent. will stay again"
The price is AED 533
AED 584 total
includes taxes & fees
3 Apr - 4 Apr
Shaker Mill Inn

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is AED 882
AED 985 total
includes taxes & fees
29 Mar - 30 Mar
Chambery Inn

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (128)
"The Trail in Adams offered me exactly what I needed: a quiet and convenient place prepare for a day in the woods the next day. Very convenient walking to nearby restaurants, right in the middle of Adams. There was a snowstorm that night, and the walks were shoveled several times that evening and the next morning. "
The price is AED 638
AED 713 total
includes taxes & fees
28 Mar - 29 Mar
The Trail in Adams - Berkshires’ Art Hotel

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"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 AED 1,441
AED 1,610 total
includes taxes & fees
31 Mar - 1 Apr
33 Main

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (151)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is AED 639
AED 714 total
includes taxes & fees
30 Mar - 31 Mar
Brook Farm Inn

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (122)
"Beautiful property, great service "
The price is AED 915
AED 1,022 total
includes taxes & fees
30 Mar - 31 Mar
Devonfield Inn B&B

Olde Judge Mansion

2.0 star property
8.6 out of 10, Excellent, (235)
"The place is gorgeous inside, lots of woodwork that is very well taken care of, Tina(the owner) is a pleasure, always helpful, vast knowledge of the area, the place is true gem."
The price is AED 510
AED 566 total
includes taxes & fees
27 Apr - 28 Apr
Olde Judge Mansion

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
Whistler's Inn Bed & Breakfast

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"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 AED 1,559
AED 1,885 total
includes taxes & fees
30 Mar - 31 Mar
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (81)
"Everything "
The price is AED 584
AED 631 total
includes taxes & fees
3 Apr - 4 Apr
Inn at Silver Maple Farm

Gardner Farm Inn

3.5 star property
10.0 out of 10, Exceptional, (176)
"My daughter and I were in town for one night to tour RPI. We certainly chose well with our overnight accommodations. Although the house is quaint, extra clean, and decorated perfectly, the star of our stay was the innkeeper, John. From the moment we walked in, it was like seeing an old friend. John was friendly, kind and took excellent care of us. His hospitality made us want to come back again....very soon. "
The price is AED 624
AED 692 total
includes taxes & fees
7 Apr - 8 Apr
Gardner Farm Inn

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"
The Inn at Stockbridge

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"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...
The price is AED 804
AED 804 total
includes taxes & fees
15 Apr - 16 Apr
Tanglewood Suites

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
The price is AED 1,561
AED 1,713 total
includes taxes & fees
11 Apr - 12 Apr
Inn at Kenmore Hall

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is AED 988
AED 1,044 total
includes taxes & fees
14 Apr - 15 Apr
Harbour House Inn

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (68)
"Lovely Inn and Innkeeper. The room was clean and cozy. There was hot coffee and breakfast in the morning including homemade breads and fruit. We will be back! "
Eastgate Inn B&B

The Red Door B&B

3.0 star property
10.0 out of 10, Exceptional, (5)
"We loved staying at this b&b. The owners were very accommodating, kind and helpful. Because of the pandemic, they only took us for the weekend. The breakfasts were above and beyond our expectations, simply fantastic. We highly recommend this beautiful place and we will be back for sure. "
The Red Door B&B
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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Other property types in Stephentown

Charming 3-bedroom Cabin for nature lovers

The price is AED 455
AED 962 total
includes taxes & fees
28 Mar - 29 Mar
Charming 3-bedroom Cabin for nature lovers

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"The location to jimney peak was great."
The price is AED 474
AED 560 total
includes taxes & fees
2 Apr - 3 Apr
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 493
AED 540 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
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 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: The Cornell Inn, Lenox & The Berkshires: 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. Chambery Inn: 9 rooms. 18.4 mi (29.7 km) from the heart of downtown. Enjoy the private yard and deli. The Trail in Adams - Berkshires’ Art Hotel: 9 rooms. Located 14.8 mi (23.8 km) from the core of Stephentown. Enjoy the unique décor and arcade game room.
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.