Default HTG hotel image

Search B&B in Stephentown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug
In one month
11 Sep - 13 Sep
In two months
9 Oct - 11 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, (113 reviews)
"Very nice hotel."
United States
Erdem
The price is ฿5,276
฿5,909 total
includes taxes & fees
31 Aug - 1 Sept
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 ฿6,198
฿6,799 total
includes taxes & fees
15 Sept - 16 Sept
Shaker Mill Inn
Exterior

3. 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 ฿8,408
฿8,888 total
includes taxes & fees
27 Aug - 28 Aug
Harbour House Inn
Property grounds

4. 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 ฿5,280
฿5,897 total
includes taxes & fees
9 Sept - 10 Sept
Whistler's Inn Bed & Breakfast
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, (154 reviews)
"Great central location for travelers there to see the sights."
United States
Jenna
The price is ฿6,877
฿7,682 total
includes taxes & fees
15 Sept - 16 Sept
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, (251 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 ฿5,052
฿5,608 total
includes taxes & fees
17 Aug - 18 Aug
Olde Judge Mansion
Property grounds

7. 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 ฿5,817
฿6,456 total
includes taxes & fees
20 Aug - 21 Aug
Gardner Farm Inn
Interior

8. 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 ฿6,927
฿7,481 total
includes taxes & fees
19 Aug - 20 Aug
The Morgan State House
Front of property

9. 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 ฿12,494
฿14,654 total
includes taxes & fees
13 Sept - 14 Sept
The Inn at Stockbridge
Front of property

10. 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 ฿8,948
฿9,995 total
includes taxes & fees
14 Sept - 15 Sept
Chambery Inn
Suite, Private Bathroom (RedBird Suite) | View from room

11. 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 ฿10,943
฿13,238 total
includes taxes & fees
31 Aug - 1 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property – evening/night

12. 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 ฿12,893
฿14,401 total
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B
Exterior

13. 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 ฿5,895
฿6,782 total
includes taxes & fees
26 Aug - 27 Aug
The Cornell Inn, Lenox & The Berkshires
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, free WiFi, 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 ฿21,964
฿24,533 total
includes taxes & fees
31 Aug - 1 Sept
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stephentown Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great location, spacious room, staff friendly and helpful."
Ginny 2-night trip
Posted 4 hours ago
Hotel Downstreet, an Ascend Collection Hotel

Find out more about Stephentown

Stephentown B&B information

Number of reviews
Accommodation
 B&B
Lowest Price
Highest Price

Frequently asked questions

Searching for B&Bs in Stephentown?
Whether you're on a romantic holiday and are looking to stay somewhere quiet, or you're travelling solo and hoping to get some tips from locals, B&Bs can be a great choice for many travellers. 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 a good option for your stay?
With attentive service, opportunities to meet other guests and of course a full breakfast, B&Bs offer 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 city centre. Enjoy the free full breakfast and unique decor. Chambery Inn: 9 rooms. 18.4 mi (29.7 km) from the city centre. Enjoy the private garden and snack bar/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 decor and patio area.
What's the best time of year to book my B&B in Stephentown?
When you're dreaming of a stay in Stephentown, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stephentown are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Stephentown?
When you want to see 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?
Mapping out your trip in and around Stephentown is easy 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 a rental car for your journey.

Explore a world of travel with Expedia