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Compare 30 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, (1003)
"Beautiful place to stay - loved it - interior decor first rate! "
The price is AED 448
AED 526 total
includes taxes & fees
12 Jan - 13 January 2025
The Cornell Inn, Lenox
Lakehouse Inn
Lake

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (233)
"We really enjoyed our stay. The breakfast was really good and the added touch of a welcome drink was really fun and made our stay feel special. We would like to come back again. "
The price is AED 474
AED 556 total
includes taxes & fees
29 Dec - 30 Dec
Lakehouse Inn
The Morgan State House
Outdoor dining

The Morgan State House

3.5 star property
9.2 out of 10, Wonderful, (493)
"Great property in prime location. Highly recommend"
The price is AED 553
AED 597 total
includes taxes & fees
31 Dec - 1 January 2025
The Morgan State House
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (361)
"Everything was amazing. It was truly an experience. "
The price is AED 698
AED 779 total
includes taxes & fees
26 Dec - 27 Dec
Chambery Inn
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (404)
"Quaint "
The price is AED 386
AED 423 total
includes taxes & fees
5 Jan - 6 January 2025
Shaker Mill Inn
Devonfield Inn B&B
Room

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (119)
"Great location "
The price is AED 1,172
AED 1,309 total
includes taxes & fees
5 Jan - 6 January 2025
Devonfield Inn B&B
33 Main
Room

33 Main

4.0 star property
10.0 out of 10, Exceptional, (69)
"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 1,337
AED 1,493 total
includes taxes & fees
20 Jan - 21 January 2025
33 Main
Gardner Farm Inn
Room

Gardner Farm Inn

3.5 star property
10.0 out of 10, Exceptional, (171)
"John was a most gracious host. The house is filled with treasures and good vibes. Clean, cozy, and authentic. Truly a great find!"
The price is AED 643
AED 713 total
includes taxes & fees
5 Jan - 6 January 2025
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, (80)
"Everything "
The price is AED 547
AED 591 total
includes taxes & fees
5 Jan - 6 January 2025
Inn at Silver Maple Farm
Tanglewood Suites
Property grounds

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
26 Dec - 27 Dec
Tanglewood Suites
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, (125)
"Stayed only one night Very cosy, quiet place "
The price is AED 597
AED 667 total
includes taxes & fees
13 Jan - 14 January 2025
The Trail in Adams - Berkshires’ Art Hotel
Olde Judge Mansion
Property entrance

Olde Judge Mansion

2.0 star property
8.6 out of 10, Excellent, (233)
"Place a beautiful but a little run down. The owner was amazing! Would stay again"
The price is AED 453
AED 503 total
includes taxes & fees
24 Dec - 25 Dec
Olde Judge Mansion
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (97)
"Very enjoyable stat."
The Inn at Stockbridge
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (149)
"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 672
AED 751 total
includes taxes & fees
3 Jan - 4 January 2025
Brook Farm Inn
Whistler's Inn Bed & Breakfast
Interior

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
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, (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
5 Jan - 6 January 2025
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 AED 3,673
AED 4,685 total
includes taxes & fees
24 Dec - 25 Dec
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 AED 3,673
AED 4,685 total
includes taxes & fees
24 Dec - 25 Dec
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Inn at Kenmore Hall
Front of property

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 1,712 total
includes taxes & fees
3 Jan - 4 January 2025
Inn at Kenmore Hall
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 AED 944
AED 998 total
includes taxes & fees
26 Dec - 27 Dec
Harbour House Inn
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

The entire Stephentown Hotel! 28 person occupancy

The entire Stephentown Hotel! 28 person occupancy

10.0 out of 10, Exceptional, (1)
"We got 7 families to all stay on the property. Lots of fun. Clean and comfortable sleeping accommodations."
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, (1750)
"Nice and quiet family get a way"
The price is AED 689
AED 792 total
includes taxes & fees
1 Jan - 2 January 2025
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is AED 694
AED 762 total
includes taxes & fees
5 Jan - 6 January 2025
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 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. Shaker Mill Inn: 9 rooms. 15.2 mi (24.4 km) from the heart of downtown.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?
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.