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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 28 B&B in Stockbridge with updated reviews, rates, and availability.

The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1000)
"Historic property with a bunch to do. Pool was great!"
The price is AED 393
AED 604 total
includes taxes & fees
28 Apr - 29 Apr
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is AED 1,559
AED 1,885 total
includes taxes & fees
6 Apr - 7 Apr
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Tanglewood Suites
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is AED 804
AED 804 total
includes taxes & fees
5 Apr - 6 Apr
Tanglewood Suites
New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
Fridge, microwave, oven, stovetop

New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge

2.0 star property
10.0 out of 10, Exceptional, (6)
"We recently rented this house for two weeks in order to spend time under the same roof with our grown children and baby grandson - and we couldn't have had a more enjoyable time! The house provided ample space for us to gather in small groups or larger ones whether we were indoors, outside on the deck or in the yard. The location in town was ideal for pushing the baby stroller along all the sidewalks as well as easily accessing all the shops and restaurants. With the Red Lion Inn only a block...
New 4500 sq ft modern 5 bed-5.5 bath on Housatonic River and walk to Stockbridge
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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Other property types in Stockbridge

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1794)
"The location to jimney peak was great."
The price is AED 437
AED 520 total
includes taxes & fees
13 Apr - 14 Apr
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 493
AED 540 total
includes taxes & fees
5 Apr - 6 Apr
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (241)
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "
The price is AED 551
AED 837 total
includes taxes & fees
7 Apr - 8 Apr
Berkshire Village Carriage House - Super Private!!
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.

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?
Check out 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. Tanglewood Suites: 2 rooms.
How many Bed & Breakfasts can I expect to find in Stockbridge?
Expedia has 5 B&Bs for your time in 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.