Search Resorts in West Stockbridge

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for West Stockbridge resorts

Dining
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Hancock
10.0 out of 10, Exceptional, (6)
"Great location, clean and perfect for a family! "
United States
Allison A.
The price is AED 2,020
AED 2,548 total
includes taxes & fees
31 Dec - 1 January 2026
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Really quiet, peaceful stay and beautiful spot for the money. Front desk staff so nice. No elevator to second floor so keep in mind if have accessibility issues/wheelchair user. Great view and gluten free menu options. Would stay again if in area. Was just passing through on way to medical appointment. "
Meaghan 1-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

What is West Stockbridge like for a resort vacation?
Longing for a relaxing escape? You deserve the comforts of a resort, where you can find everything you want for your vacation from convenient dining options to activities and entertainment. Browse the resorts in the area and discover the best one for you, whether you envision yourself kicking back in a suite with stunning views or hitting the golf course for an afternoon game.
What's the best resort in West Stockbridge?
Our top-rated resort near West Stockbridge: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 6.4 mi (10.3 km) from West Stockbridge. Enjoy the sauna, fitness center, and terrace.
What can I do in West Stockbridge?
Travelers enjoy exploring the gardens, and also have good things to say about the dining options here. If you brought the kids, you can head to Charles H. Baldwin & Sons or Hotchkiss Mobile Studio for some family fun. For more to see in the area, you can spend time at Stockbridge Bowl or Ebenezer II Gifts and Antiques.
What's the weather like in West Stockbridge?
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 West Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around West Stockbridge?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 7.4 mi (11.9 km) away from the city center. 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, consider renting a car to take in more sights.

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