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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 27 B&B in Stephentown with updated reviews, rates, and availability.

The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Quiet, friendly, convenient"
The price is AED 491
AED 692 total
includes taxes & fees
5 May - 6 May
The Cornell Inn, Lenox & The Berkshires
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (257)
"Wonderful Location"
Lakehouse Inn
The Morgan State House
Terrace/patio

The Morgan State House

3.5 star property
9.2 out of 10, Wonderful, (507)
"Stunning rooms, very friendly staff"
The price is AED 706
AED 763 total
includes taxes & fees
12 May - 13 May
The Morgan State House
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (410)
"Nice"
The price is AED 522
AED 573 total
includes taxes & fees
15 May - 16 May
Shaker Mill Inn
Chambery Inn
Front of property

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 698
AED 779 total
includes taxes & fees
11 May - 12 May
Chambery Inn
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, (129)
"Best place I have been. Beautiful place. Excellent host. "
The price is AED 638
AED 713 total
includes taxes & fees
5 May - 6 May
The Trail in Adams - Berkshires’ Art Hotel
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"Beautiful place. Everything was perfect and so pretty. Great location, too. Will definitely return. "
The price is AED 1,323
AED 1,478 total
includes taxes & fees
7 May - 8 May
33 Main
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (151)
"Very homy kind of Inn. Owner was very accommodative and friendly. Very safe place with great ambience. "
The price is AED 1,104
AED 1,233 total
includes taxes & fees
16 May - 17 May
Brook Farm Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (124)
"Very enjoyable comfortable stay"
The price is AED 988
AED 1,104 total
includes taxes & fees
5 May - 6 May
Devonfield Inn B&B
Olde Judge Mansion
Property entrance

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 465
AED 516 total
includes taxes & fees
6 May - 7 May
Olde Judge Mansion
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"Great historic inn loaded with interesting common areas and furnishings."
The price is AED 601
AED 741 total
includes taxes & fees
19 May - 20 May
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is AED 2,530
AED 3,061 total
includes taxes & fees
15 May - 16 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (85)
"Everything about our stay in The Loft was wonderful! The hot breakfast each morning was incredible. The entire inn was very clean and well kept. We will definitely be back! "
The price is AED 584
AED 631 total
includes taxes & fees
6 May - 7 May
Inn at Silver Maple Farm
Gardner Farm Inn
Property grounds

Gardner Farm Inn

3.5 star property
10.0 out of 10, Exceptional, (176)
"Friendly inn keeper, great breakfast, comfortable beds. Fun place to stay!"
The price is AED 585
AED 649 total
includes taxes & fees
6 May - 7 May
Gardner Farm Inn
The Inn at Stockbridge
Exterior

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 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets

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. "
The price is AED 988
AED 988 total
includes taxes & fees
5 May - 6 May
Tanglewood Suites
Inn at Kenmore Hall
Lobby

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
5 May - 6 May
Inn at Kenmore Hall
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Nice place for a weekend away."
The price is AED 867
AED 917 total
includes taxes & fees
2 Jun - 3 Jun
Harbour House Inn
Eastgate Inn B&B
Porch

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (68)
"Great host and enjoyable stay."
Eastgate Inn B&B
The Red Door B&B
Interior

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
Interior

Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1803)
"The property was clean and the staff very accommodated."
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, (928)
"Staff was exceptionally helpful and friendly."
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, Taconic Ridge State Forest and Zema’s Nursery 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. Chambery Inn: 9 rooms. Situated 18.4 mi (29.7 km) from the heart of Stephentown. Enjoy the private yard and deli. Whistler’s Inn Bed & Breakfast: 14 rooms. 14.4 mi (23.1 km) from the heart of downtown. Enjoy the private yard and unique décor. Lakehouse Inn: 14 rooms. Located 17.1 mi (27.6 km) from the core of Stephentown. Enjoy the free full breakfast 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 Taconic Ridge State Forest and Zema’s Nursery. Jiminy Peak Mountain Resort and Mount Lebanon 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.