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Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sep - 6 Sep
In two months
2 Oct - 4 Oct

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, (112 reviews)
"Very nice hotel."
United States
Erdem
The price is AED 694
AED 778 total
includes taxes & fees
10 Aug - 11 Aug
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, (465 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is AED 698
AED 766 total
includes taxes & fees
8 Sep - 9 Sep
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, (1,002 reviews)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is AED 634
AED 729 total
includes taxes & fees
31 Aug - 1 Sep
The Cornell Inn, Lenox & The Berkshires
Exterior

4. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (55 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is AED 890
AED 941 total
includes taxes & fees
8 Sep - 9 Sep
Harbour House Inn
Terrace/patio

5. 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, (152 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is AED 758
AED 846 total
includes taxes & fees
10 Aug - 11 Aug
The Trail in Adams - Berkshires’ Art Hotel
Property entrance

6. Olde Judge Mansion

Olde Judge Mansion
2.0 star property
Troy
8.8 out of 10, Excellent, (250 reviews)
"My husband and I enjoyed our stay! We were in the area for the weekend for DMB's shows at SPAC- 30 min drive. Tina (owner/ host) was exceptional. She was extremely communicative. The property was clean and held its historic charm. Breakfast was fantastic and made to order. We felt safe with the security system in place. Off street parking provided. Tina was lovely and easy to talk to. She is very knowledgeable about the city of Troy and its history. This will be our new go to when we are in the...
United States
Megan
The price is AED 543
AED 603 total
includes taxes & fees
9 Aug - 10 Aug
Olde Judge Mansion
Property grounds

7. Gardner Farm Inn

Gardner Farm Inn
3.5 star property
Troy
10.0 out of 10, Exceptional, (215 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 AED 629
AED 698 total
includes taxes & fees
20 Aug - 21 Aug
Gardner Farm Inn
Property grounds

8. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (509 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is AED 585
AED 654 total
includes taxes & fees
19 Aug - 20 Aug
Whistler's Inn Bed & Breakfast
Front of property

9. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (171 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is AED 976
AED 1,119 total
includes taxes & fees
16 Aug - 17 Aug
Brook Farm Inn
Interior

10. The Morgan State House

The Morgan State House
3.5 star property
Albany
9.2 out of 10, Wonderful, (555 reviews)
"very comfortable bed and pillows!"
United States
Mary
The price is AED 729
AED 788 total
includes taxes & fees
25 Aug - 26 Aug
The Morgan State House
Front of property

11. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (383 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
The price is AED 992
AED 1,108 total
includes taxes & fees
10 Aug - 11 Aug
Chambery Inn
Front of property

12. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (101 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 AED 1,450
AED 1,701 total
includes taxes & fees
7 Sep - 8 Sep
The Inn at Stockbridge
Suite, Private Bathroom (RedBird Suite) | View from room

13. 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 AED 1,213
AED 1,467 total
includes taxes & fees
24 Aug - 25 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property - evening/night

14. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is AED 1,429
AED 1,596 total
includes taxes & fees
3 Sep - 4 Sep
Devonfield Inn B&B
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), individually decorated

15. 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 AED 2,623
AED 2,930 total
includes taxes & fees
31 Aug - 1 Sep
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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Love this hotel for going to Mass MoCA"
Victoria 1-night trip
Posted 1 hour ago
Hotel Downstreet, an Ascend Collection Hotel

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 Pontoosuc Lake 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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