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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Stephentown bed & breakfast

Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (440)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is AED 388
AED 425 total
includes taxes & fees
13 Jan - 14 Jan
Shaker Mill Inn
Porch
Lakehouse Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is AED 676
AED 793 total
includes taxes & fees
16 Jan - 17 Jan
Lakehouse Inn
Exterior
Harbour House Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"Nice place for a weekend away."
United States
Gregory
The price is AED 790
AED 835 total
includes taxes & fees
12 Jan - 13 Jan
Harbour House Inn
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (144)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is AED 638
AED 713 total
includes taxes & fees
9 Jan - 10 Jan
The Trail in Adams - Berkshires’ Art Hotel
Front of property
Chambery Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (374)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is AED 877
AED 1,029 total
includes taxes & fees
12 Jan - 13 Jan
The Inn at Stockbridge
Aerial view
Inn at Silver Maple Farm

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
The price is AED 474
AED 531 total
includes taxes & fees
7 Jan - 8 Jan
Inn at Silver Maple Farm
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AED 1,367
AED 1,527 total
includes taxes & fees
18 Jan - 19 Jan
33 Main
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is AED 866
AED 1,133 total
includes taxes & fees
7 Jan - 8 Jan
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lobby
Inn at Kenmore Hall

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is AED 1,561
AED 1,712 total
includes taxes & fees
20 Jan - 21 Jan
Inn at Kenmore Hall
Business center
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is AED 1,403
AED 1,697 total
includes taxes & fees
19 Jan - 20 Jan
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1003)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is AED 526
AED 605 total
includes taxes & fees
7 Jan - 8 Jan
The Cornell Inn, Lenox & The Berkshires
Property entrance
Olde Judge Mansion

Olde Judge Mansion

Olde Judge Mansion
2.0 star property
Troy
8.8 out of 10, Excellent, (246)
"Cozy, old fashioned mansion, well maintained and comfortable. Easy off street parking. Owner, Tina, supplied ample information about check-in and local dining. "
United States
Donald
The price is AED 504
AED 559 total
includes taxes & fees
9 Jan - 10 Jan
Olde Judge Mansion
Property grounds
Gardner Farm Inn

Gardner Farm Inn

Gardner Farm Inn
3.5 star property
Troy
10.0 out of 10, Exceptional, (201)
"Everything was excellent including the host"
United States
Lucas
The price is AED 550
AED 610 total
includes taxes & fees
9 Jan - 10 Jan
Gardner Farm Inn
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AED 866
AED 1,133 total
includes taxes & fees
7 Jan - 8 Jan
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, WiFi, bed sheets
Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is AED 929
AED 1,204 total
includes taxes & fees
7 Jan - 8 Jan
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, bed sheets
Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is AED 991
AED 1,284 total
includes taxes & fees
7 Jan - 8 Jan
Cozy Carriage House room with a double bed and private balcony
Terrace/patio
Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AED 1,053
AED 1,364 total
includes taxes & fees
7 Jan - 8 Jan
Historic Susan B. Anthony Room - Cozy & Charming Stay
Fireplace
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
The price is AED 1,334
AED 1,744 total
includes taxes & fees
7 Jan - 8 Jan
Experience Timeless Elegance in The Niles Johnson Room at The Cornell 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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Top Stephentown Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Very good "
Fernando 5-night trip
Posted 11 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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. Brook Farm Inn: 15 rooms. Situated 14.9 mi (24 km) from the heart of Stephentown. Enjoy the free cooked breakfast and outdoor pool. 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?
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 Mountain Coaster 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.