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Check prices for these dates

Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18

Our top choices for Stephentown bed & breakfast

Aerial view

1. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (113 reviews)
"Very nice hotel."
United States
Erdem
The price is P8,541
P9,566 total
includes taxes & fees
Sep 1 - Sep 2
Inn at Silver Maple Farm
Garden

2. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (466 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is P11,552
P12,673 total
includes taxes & fees
Sep 8 - Sep 9
Shaker Mill Inn
Exterior

3. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is P10,929
P12,574 total
includes taxes & fees
Aug 25 - Aug 26
The Cornell Inn, Lenox & The Berkshires
Terrace/patio

4. 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, (154 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is P12,443
P13,899 total
includes taxes & fees
Sep 14 - Sep 15
The Trail in Adams - Berkshires’ Art Hotel
Property grounds

5. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (513 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is P9,789
P10,934 total
includes taxes & fees
Sep 13 - Sep 14
Whistler's Inn Bed & Breakfast
Property grounds

6. Gardner Farm Inn

Gardner Farm Inn
3.5 star property
Troy
10.0 out of 10, Exceptional, (217 reviews)
"This is the most beautiful Inn. I felt like I was in an art exhibit. John was very welcoming and breakfast was delicious."
United States
Joanna
The price is P10,784
P11,971 total
includes taxes & fees
Aug 20 - Aug 21
Gardner Farm Inn
Property entrance

7. Olde Judge Mansion

Olde Judge Mansion
2.0 star property
Troy
8.8 out of 10, Excellent, (253 reviews)
"We love the woodwork that was never painted - BEAUTIFUL! Breakfast was a feast to behold - Delicious! Our hostess was delightful and gave us her best suggestion for dinner - glad we listened."
United States
EDNA
The price is P9,367
P10,398 total
includes taxes & fees
Aug 20 - Aug 21
Olde Judge Mansion
Front of property

8. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (384 reviews)
"The room was clean and very quiet. Breakfast was delivered to our room as requested."
United States
Richard
The price is P16,591
P18,532 total
includes taxes & fees
Sep 16 - Sep 17
Chambery Inn
Interior

9. The Morgan State House

The Morgan State House
3.5 star property
Albany
9.2 out of 10, Wonderful, (558 reviews)
"very comfortable bed and pillows!"
United States
Mary
The price is P12,843
P13,870 total
includes taxes & fees
Aug 20 - Aug 21
The Morgan State House
Front of property

10. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (102 reviews)
"Our room was very clean and comfortable - exactly what we needed to rest well. Breakfast was excellent and we felt well taken care of. We are grateful for the friendly and welcoming hosts and their staff who listened to every need and graciously provided for us. We’ll definitely return for another stay when we’re in the area."
United Kingdom
Michele
The price is P23,165
P27,170 total
includes taxes & fees
Sep 13 - Sep 14
The Inn at Stockbridge
Front of property - evening/night

11. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Excellent food and helpful staff"
United States
Richard
The price is P23,904
P26,700 total
includes taxes & fees
Sep 3 - Sep 4
Devonfield Inn B&B
View from room

12. 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, (114 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is P20,289
P24,543 total
includes taxes & fees
Aug 31 - Sep 1
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior

13. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (56 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is P15,590
P16,478 total
includes taxes & fees
Aug 18 - Aug 19
Harbour House Inn
Premium bedding, iron/ironing board, WiFi (free), individually decorated

14. 33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (75 reviews)
"This was our second stay at 33 Main. Wonderfully maintain, homey environment, with friendly, welcoming and helpful staff. Welcoming cookies, and beautiful water bottle. They even remembered that we asked for the beach and gave us excellent recommendation. Convenient parking in the back. My only suggestion for improvement is breakfast - last year it was much better."
United States
Tatyana
The price is P40,722
P45,486 total
includes taxes & fees
Aug 31 - Sep 1
33 Main
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Place was clean and well equipped, pool and amenities were great too !"
Nyra 3-night trip
Posted 9 hours ago
Vacation Village in the Berkshires

Find out more about Stephentown

Stephentown B&B information

Number of reviews
3,125
Accommodation
26 B&B
Lowest Price
P9,566
Highest Price
P45,486

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: Berkshire Mountain House: 7 rooms. 2.4 mi (3.9 km) from the heart of Stephentown. Enjoy the free buffet breakfast and rooftop terrace. The Cornell Inn, Lenox & The Berkshires: 14.2 mi (22.8 km) from the downtown core. Enjoy the free full breakfast and unique décor. 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 patio area.
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.

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