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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Browse Select West Stockbridge B&B

Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (400)
"A positively delightful B&B in a beautiful town. "
The price is Rp1.697.745
Rp1.952.407 total
includes taxes & fees
19 Aug - 20 Aug
Locust Tree Bed and Breakfast LLC
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is Rp2.064.458
Rp2.938.126 total
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires
Changing Times Boutique Country Lodging
Porch

Changing Times Boutique Country Lodging

3.5 star property
10.0 out of 10, Exceptional, (103)
"The b and b is charming and comfortable. Loretta was extremely welcoming and accommodating."
The price is Rp2.829.575
Rp3.169.124 total
includes taxes & fees
19 Aug - 20 Aug
Changing Times Boutique Country Lodging
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (421)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is Rp2.926.589
Rp3.210.468 total
includes taxes & fees
19 Aug - 20 Aug
Shaker Mill Inn
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (126)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is Rp2.657.375
Rp3.055.981 total
includes taxes & fees
2 Sept - 3 Sept
Blackberry River Inn
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
The price is Rp4.241.129
Rp4.482.855 total
includes taxes & fees
2 Sept - 3 Sept
Harbour House Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Wilder House Berkshires
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated

Wilder House Berkshires

2.0 star property
9.6 out of 10, Exceptional, (29)
"Brads and Lara both served a fabulous breakfast. So friendly and welcoming! The bed was very comfortable. Only complaint was that the cabinet, closet door needs to be greased with WD 40 please on the hinges! A terrible & loud screeching noise!"
The price is Rp2.794.003
Rp3.120.901 total
includes taxes & fees
9 Sept - 10 Sept
Wilder House Berkshires
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (481)
"Nice quaint out of the ordinary vacation experience. "
The price is Rp2.802.734
Rp3.130.642 total
includes taxes & fees
19 Aug - 20 Aug
Whistler's Inn Bed & Breakfast
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (156)
"Wonderful cozy and warm feel. Property, location and service are all excellent."
Brook Farm Inn
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is Rp10.008.611
Rp11.179.618 total
includes taxes & fees
25 Aug - 26 Aug
33 Main
Tanglewood Suites
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi

Tanglewood Suites

2.5 star property
7.4 out of 10, Good, (18)
"Made a Friday night reservation for their 2BR suite in August. When we arrived at the location listed on Expedia, we found ourselves in a residential neighborhood with no "Tanglewood Suites" in sight. I had emailed in advance for clarification on the location but didn't get a reply. We called the place and the proprietor said there was no record of a reservation and that she never rents for one night only. We were left high and dry with no reasonably priced play to stay in the area. "
The price is Rp4.349.461
Rp4.349.461 total
includes taxes & fees
19 Aug - 20 Aug
Tanglewood Suites
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 West Stockbridge Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"This is my "go to" when I'm in Pittsfield. It's central, convenient, clean and comfortable."
Dane 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

Searching for B&Bs in West Stockbridge?
If you're interested in something a little quirkier than the traditional hotel experience, a stay at a bed and breakfast might be the perfect option for your trip. When you want to explore some attractions in town, Stockbridge Bowl and Charles H. Baldwin & Sons are worth a stop.
How do you know if a B&B is the best choice for your stay?
B&Bs all have a unique charm — whether it's a picturesque garden or a beautiful breakfast room, the quaint details are what make bed and breakfasts a fun place to get away.
What are the best bed and breakfasts in West Stockbridge?
Here are some B&Bs in the surrounding area: Shaker Mill Inn: 9 rooms. 0.1 mi (0.2 km) from the heart of West Stockbridge. The Cornell Inn, Lenox & The Berkshires: 4.9 mi (7.9 km) from the city centre. Enjoy the free full breakfast and unique decor. Whistler's Inn Bed & Breakfast: 14 rooms. Located 4.8 mi (7.7 km) from the core of West Stockbridge. Enjoy the private garden and unique decor.
What's the best time of year to book my B&B in West Stockbridge?
When you're planning your getaway to West Stockbridge, make sure that you take the year-round temperatures into account. 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 West Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in West Stockbridge?
Travellers enjoy West Stockbridge for its gardens and restaurants. If you're looking to find something to do during your travels, you might consider visiting Charles H. Baldwin & Sons and Hoffman's Pottery. You should put Stockbridge Bowl and Hotchkiss Mobile Studio on your list if you want to see more of the area.
How can I get to and around West Stockbridge?
You can plan your excursions in and around West Stockbridge ahead of time with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 7.4 mi (11.9 km) from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 17.8 mi (28.7 km) away. If you'd like to explore around the area, you may want a rental car for your journey.