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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

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
9.0 out of 10, Wonderful, (1000)
"My room was adorable...completely charming and well appointed. I appreciated the phone call with detailed late check-in instructions and when I arrived the property manager walked me to my room. Breakfast was lovely and the staff very friendly. Town a is an easy walk."
The price is AED 448
AED 526 total
includes taxes & fees
26 Jan - 27 Jan
The Cornell Inn, Lenox
Lakehouse Inn
Lake

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (239)
"Amazing breakfast!"
The price is AED 463
AED 543 total
includes taxes & fees
25 Jan - 26 Jan
Lakehouse Inn
The Morgan State House
Outdoor dining

The Morgan State House

3.5 star property
9.2 out of 10, Wonderful, (494)
"Great property in prime location. Highly recommend"
The price is AED 534
AED 577 total
includes taxes & fees
7 Feb - 8 Feb
The Morgan State House
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (362)
"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 698
AED 779 total
includes taxes & fees
29 Jan - 30 Jan
Chambery Inn
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
25 Jan - 26 Jan
Tanglewood Suites
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
26 Jan - 27 Jan
33 Main
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (406)
"Beautiful inn. It was nice and quiet, exactly what I needed. "
The price is AED 386
AED 423 total
includes taxes & fees
26 Jan - 27 Jan
Shaker Mill Inn
Devonfield Inn B&B
Room

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (121)
"Great location "
The price is AED 1,025
AED 1,145 total
includes taxes & fees
26 Jan - 27 Jan
Devonfield Inn B&B
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 698
AED 780 total
includes taxes & fees
25 Jan - 26 Jan
Brook Farm Inn
Gardner Farm Inn
Room

Gardner Farm Inn

3.5 star property
10.0 out of 10, Exceptional, (174)
"John is a very cordial host and he made us feel like old friends upon our arrival. The building is an old farmhouse that is updated just enough to give it modern touches but also keep it's historic character while the decor is whimsical and creative in it's hodge podge way."
The price is AED 636
AED 706 total
includes taxes & fees
25 Jan - 26 Jan
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 511
AED 551 total
includes taxes & fees
25 Jan - 26 Jan
Inn at Silver Maple Farm
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, (127)
"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 592
AED 662 total
includes taxes & fees
25 Jan - 26 Jan
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 493
AED 547 total
includes taxes & fees
26 Jan - 27 Jan
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
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
26 Jan - 27 Jan
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
25 Jan - 26 Jan
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
25 Jan - 26 Jan
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
25 Jan - 26 Jan
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
27 Jan - 28 Jan
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, (1757)
"It had a great pool and hot tub. also right near the ski area, jiminey Peak."
The price is AED 551
AED 641 total
includes taxes & fees
2 Feb - 3 Feb
Vacation Village in the Berkshires
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (235)
"Very lovely place to stay. Everything was clean and the owner made everything simple."
The price is AED 551
AED 833 total
includes taxes & fees
26 Jan - 27 Jan
Berkshire Village Carriage House - Super Private!!
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. Chambery Inn: 9 rooms. 18.4 mi (29.7 km) from the heart of downtown. Enjoy the private yard and deli. Shaker Mill Inn: 9 rooms. Located 15.2 mi (24.4 km) from the core of Stephentown.
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.