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Our top choices for Stockbridge bed & breakfast

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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is AED 1,137
AED 1,375 total
includes taxes & fees
25 May - 26 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (449 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is AED 400
AED 438 total
includes taxes & fees
10 May - 11 May
Shaker Mill Inn

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is AED 697
AED 779 total
includes taxes & fees
7 May - 8 May
The Berkshire Mountain Inn

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (176 reviews)
"Charming, quiet, clean very clean with a beautiful dining room for breakfast and very respectful service."
United States
Mara
The price is AED 549
AED 631 total
includes taxes & fees
7 May - 8 May
Blackberry River Inn

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is AED 918
AED 970 total
includes taxes & fees
7 May - 8 May
Harbour House Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is AED 628
AED 702 total
includes taxes & fees
7 May - 8 May
Chambery Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is AED 988
AED 1,104 total
includes taxes & fees
7 May - 8 May
Devonfield Inn B&B

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (46 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is AED 697
AED 779 total
includes taxes & fees
18 May - 19 May
Wilder House Berkshires

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is AED 965
AED 1,132 total
includes taxes & fees
21 May - 22 May
The Inn at Stockbridge

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is AED 939
AED 1,049 total
includes taxes & fees
24 May - 25 May
Whistler's Inn Bed & Breakfast

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is AED 791
AED 1,035 total
includes taxes & fees
7 May - 8 May
Experience Timeless Elegance in The Edith Wharton Room!

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is AED 386
AED 444 total
includes taxes & fees
7 May - 8 May
Locust Tree Bed and Breakfast LLC

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AED 2,399
AED 2,679 total
includes taxes & fees
7 May - 8 May
33 Main

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 791
AED 1,035 total
includes taxes & fees
7 May - 8 May
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Delicious breakfast and beautiful room!"
United States
Laarni
The price is AED 475
AED 546 total
includes taxes & fees
7 May - 8 May
The Cornell Inn, Lenox & The Berkshires

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 967
AED 1,257 total
includes taxes & fees
11 May - 12 May
Elegant Carriage House room with a queen bed and private patio.

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 1,026
AED 1,337 total
includes taxes & fees
7 May - 8 May
Cozy Carriage House room with a double bed and private balcony

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is AED 1,085
AED 1,413 total
includes taxes & fees
7 May - 8 May
Historic Susan B. Anthony Room - Cozy & Charming Stay

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 1,350
AED 1,753 total
includes taxes & fees
10 May - 11 May
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is AED 1,467
AED 1,868 total
includes taxes & fees
7 May - 8 May
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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 Stockbridge Hotel Reviews

Frequently asked questions

Searching for B&Bs in Stockbridge?
If you want to find a place to stay with fewer rooms than a hotel and a cozy environment, a B&B might be a great fit for your vacation to Stockbridge. A trip to Stockbridge wouldn't be complete without a stop by Norman Rockwell Museum or Mission House if you're someone who could spend hours browsing exhibits.
Why would you choose B&Bs instead of traditional hotels?
Every B&B has a unique charm. Whether it's a garden for guests to admire or a beautiful dining room, the little details are what make bed and breakfasts the perfect escape.
What are the top B&Bs in Stockbridge?
Here are some well-liked B&Bs in the surrounding area: The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: 8 rooms. 1.3 mi (2.1 km) from the heart of Stockbridge. Enjoy the free full breakfast and outdoor pool. The Cornell Inn, Lenox & The Berkshires: 5.8 mi (9.3 km) from the downtown core. Enjoy the free full breakfast and unique décor. Locust Tree Bed and Breakfast LLC: 7 rooms. 18.6 mi (30 km) from the heart of downtown.Shaker Mill Inn: 9 rooms. Located 4.2 mi (6.7 km) from the core of Stockbridge.
What's the best time of year to book my B&B in Stockbridge?
When you're planning your stay in Stockbridge, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Stockbridge?
Travelers enjoy Stockbridge for its bars and historic landmarks. If cultural attractions are high on your list, Norman Rockwell Museum and Mission House are spots to check out. You might put Naumkeag Museum and National Shrine of the Divine Mercy on your list if you want to see more of the area.
How can I get to and around Stockbridge?
You can map out your trip in and around Stockbridge ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 9.6 mi (15.5 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 20 mi (32.3 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.