A nighttime view of a residential area with houses adorned with holiday lights.

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Check prices for these dates

Next weekend
21 Aug - 23 Aug
In two weeks
28 Aug - 30 Aug
In one month
11 Sept - 13 Sept
In two months
9 Oct - 11 Oct

Our top choices for Stockbridge bed & breakfast

View from room

1. 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 RM1,351
RM1,634 total
includes taxes & fees
25 Aug - 26 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

2. 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 RM1,642
RM1,926 total
includes taxes & fees
8 Sept - 9 Sept
The Inn at Stockbridge
Garden

3. 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 RM798
RM875 total
includes taxes & fees
8 Sept - 9 Sept
Shaker Mill Inn
Exterior

4. 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)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is RM728
RM837 total
includes taxes & fees
25 Aug - 26 Aug
The Cornell Inn, Lenox & The Berkshires
Front of property – evening/night

5. 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 RM1,591
RM1,777 total
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B
Property grounds

6. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (511 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
The price is RM652
RM728 total
includes taxes & fees
1 Sept - 2 Sept
Whistler's Inn Bed & Breakfast
Front of property

7. 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 RM1,104
RM1,234 total
includes taxes & fees
13 Aug - 14 Aug
Chambery Inn
Desk, laptop workspace, iron/ironing board (on request), free WiFi

8. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (104 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
The price is RM1,125
RM1,257 total
includes taxes & fees
17 Aug - 18 Aug
Granville House
Aerial view

9. 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 RM814
RM912 total
includes taxes & fees
3 Sept - 4 Sept
Inn at Silver Maple Farm
Interior detail

10. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (61 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is RM854
RM953 total
includes taxes & fees
27 Aug - 28 Aug
Wilder House Berkshires
Premium bedding, iron/ironing board, free WiFi, individually decorated

11. 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 RM2,711
RM3,028 total
includes taxes & fees
31 Aug - 1 Sept
33 Main
Exterior

12. Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (438 reviews)
"This is a quiet location and easy to find. It has a working-farm vibe rather than a luxury-vacation vibe. French toast was delicious. Guest meals are prepared in a home kitchen without a dishwasher or secondary sink."
United States
Kay
The price is RM430
RM494 total
includes taxes & fees
16 Aug - 17 Aug
Locust Tree Bed and Breakfast LLC
Front of property

13. 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 RM1,087
RM1,247 total
includes taxes & fees
16 Aug - 17 Aug
Brook Farm Inn
Library

14. Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (202 reviews)
"Excellent breakfast, very nice staff."
United States
Leslie
The price is RM777
RM894 total
includes taxes & fees
17 Aug - 18 Aug
Blackberry River 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 Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Pool and staff was great"
peter 2-night trip
Posted less than an hour ago
Vacation Village in the Berkshires

Find out more about Stockbridge

Stockbridge B&B information

Number of reviews
3,551
Accommodation
27 B&B
Lowest Price
RM494
Highest Price
RM3,028

Frequently asked questions

Searching for B&Bs in Stockbridge?
If you want to find some accommodation with fewer rooms than the traditional hotel and a more personalised environment, a B&B might be just the right fit for your trip to Stockbridge. A trip to Stockbridge wouldn't be complete without a stop at Norman Rockwell Museum or Mission House if you're someone who could spend hours browsing exhibits.
Why should you consider a B&B versus a traditional hotel?
Every B&B has a unique charm — whether it's a cosy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the little details are what make bed and breakfasts a fun place to get away.
What are the top B&Bs in Stockbridge?
Take a look at these B&Bs in Stockbridge: The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: 8 rooms. Enjoy the free full breakfast and outdoor pool. The Inn at Stockbridge: 14 rooms. Enjoy the free cooked breakfast and designer toiletries.
When should I book my B&B in Stockbridge?
When you're planning your escape to Stockbridge, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Stockbridge?
Travellers enjoy Stockbridge for its bars and historic landmarks. If cultural attractions are high on your list, Norman Rockwell Museum and Berkshire Theatre Festival are spots to visit. You should 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. 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.

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