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Winter Fun in the Berkshires at Club Wyndham Bentley Brook

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Posted on January 25, 2023

The winter mountain wonderland that is the Berkshires in western Massachusetts offers terrific skiing, snowboarding and a variety of things to do in winter. But the best place to experience it all, put up your feet and enjoy all the comforts of home while on vacation is at Club Wyndham Bentley Brook.

Part of the Appalachian Mountains, the Berkshires are weaved through the communities of Hancock, Lenox, Pittsfield, Lee, Stockbridge and more in a wonderful pathway carved through the landscape near the border with New York state.

In the northern part of the region sits the timeshare resort Club Wyndham Bentley Brook, perfectly positioned in the Berkshire ski mountains at Jiminy Peak. Everything you need for a fabulous Berkshire ski resort vacation is here, from the Cricket Triple lift a mere 250 ft away to the taverns, restaurants and activities that are a part of the Jiminy Peak Mountain Resort complex.

Staying at Club Wyndham Bentley Brook in the Berkshires

Club Wyndham Bentley Brook in the Berkshires

Because Bentley Brook sits right at the base of Jiminy Peak, you’ll not only have all the comfort of this Club Wyndham resort but the convenience of being at one of the leading ski resorts in New England.

Six lifts are within close proximity to Club Wyndham Bentley Brook, with nine in all across the mountain ready for you to hop on. You’re literally steps away from Christiansen’s Tavern and, for any last minute groceries or maybe a bottle of wine to take back to your suite, walk over to The Country Store.

After a day on the slopes, it’s refreshing to know you can return to a resort that lets you really relax, from soaking away the soreness in the hot tub to gathering around the fire pit. But one of the best parts is that you can be assured of a ski vacation every year by buying timeshare or Club Wyndham points.

Ski season is relatively short-lived and the best ski weeks available can be hard to come by. When buying timeshare, you can secure your favorite week before they become available on the open market. With resale prices discounted 50-60% off resort prices, the deal becomes even better.

Accommodation Layouts

accommodation layouts

Accommodations at Club Wyndham Bentley Brook range from Studio units to one- and two-bedroom suites. Each layout comes with a fully equipped kitchen, which is rare in a timeshare resort and lets you save on dining costs by preparing some meals in your unit.

Studio units are a bit larger than the usual one-room units at 404 square feet and come with designated living room and dining area, again a pleasant surprise in a studio. The primary bed is a queen-sized Murphy bed that pulls down, which gives you the extra space to enjoy in your unit when you’re not asleep. The sofa pulls out into a queen bed as well, so the unit sleeps up to four comfortably.

One-bedroom suites are 781 square feet in size and can sleep up to 8 people between the two queen beds in the bedroom, the Murphy bed in the living room and the queen-sized sleeper sofa. The Suite comes with two bathrooms as well as the full living room, kitchen and dining area – plus a balcony or patio to enjoy a cup of coffee when looking out over the snow-blanketed landscape.

The largest suites at up to 1432 square feet in size, the two-bedroom units have it all and also sleep up to 8 people. Enjoy the king bed in the master bedroom, with two queen beds in the second bedroom and the queen sleeper sofa.

Two bathrooms, full kitchen, living room, dining table and convenient in-unit washer/dryer give you all of the conveniences of a vacation home. And maybe more with the Whirlpool tub in the master bathroom and the terrific views from the balcony.

Resort Amenities and Activities

resort amenities and activities

A great benefit of Wyndham Bentley Brook is the location – since the amenities at Jiminy Peak are like bonus amenities adding value to the resort. The ski in-ski out access is big, as is the storage option for your ski equipment, but there is also the sauna and hot tub to soak away your cares when you get back from the slopes.

The indoor pool is a nice reward during the winter, with an arcade game room and movie theater to entertain family members of any age. Fire pits are always fun, while the warmer months take you to the outdoor pool and other activities like tennis, basketball, the outdoor barbeque area for some grilling and the hiking, horseback riding and mountain biking the area offers in summer.

Plus, during Autumn the fall foliage is legendary so keep that in mind as well when looking for an alternative time for a vacation. One of the great things about Club Wyndham points is that you can spilt them up to use for multiple, shorter stays. Maybe for a long, leaf-peeping weekend and then a few days of skiing once the calendar turns to winter.

Winter Activities in the Berkshires

winter activities in the Berkshires

We can’t overemphasize how impressive the Jiminy Peak Mountain Resort is – much more than just some slopes and lifts that you pull up to.

Day and night skiing is available at this Berkshire ski resort with nine lifts and trails for all skill levels ranging from easy to Low Intermediate, Intermediate, High Intermediate, Most Difficult and Extremely Difficult. Six Black Diamond and three Double Black Diamond trails are on offer, if you dare.

With an elevation of 2380 ft, the 45 skiing and snowboarding trails cover over 167 acres, with all trails funneling back to the base area. Various lesson programs cater to everyone from the first-time beginner to kids-only KidsRule program, group lessons, private lessons and even adaptive lessons for those with physical, cognitive, and developmental disabilities.

For those looking for a ski style that is a bit different, try Snowshoeingwhich is a type of cross-country skiing. It gives a great, aerobic-type activity around the perimeter of the property with terrific views of the Jericho Valley or through the rolling New England forest. Snowshoeing equipment is available to rent onsite, as is all types of ski equipment.

Even during winter, live entertainment is featured at Christiansen's Tavern through the Peak Music Series, so check the Jiminy Peak website for the artist’s performing schedule.

For those looking for a different set of slopes for a change of pace, head down to Bousquet Mountain just south of Pittsfield. With four lifts and 22 trails it is smaller than Jiminy but does offer snow tubing which is great for the kids.

Places to Go Near Club Wyndham Bentley Brook