Wind in the Pines

The Resort & Its Setting

Wind in the Pines is an independently run timeshare resort in Great Barrington, a Berkshire County town known for its mix of rural New England character and cultural depth. The resort's RCI affiliation means owners aren't limited to using their week on-site — it can also be put toward an exchange elsewhere in the RCI network, which gives a week here more flexibility than a purely fixed-use property.

The Area & Things to Do

Great Barrington sits in a region built around four-season outdoor life and arts programming. Tanglewood Music Center, the Boston Symphony Orchestra's summer home, is about 3 miles away and runs concerts from June through August. The Norman Rockwell Museum (roughly 5 miles) and Berkshire Botanical Garden (around 7 miles) round out the cultural and horticultural side of things, while Monument Mountain (2 miles) offers hiking with wide Berkshires views, and the Housatonic River, less than a mile out, is popular for kayaking and fishing. Downtown Great Barrington, about a mile from the resort, is a walkable mix of independent restaurants, galleries, antique shops and a weekly farmers market. Each season brings something different — spring festivals, summer concerts and markets, fall foliage and hiking, and quieter winter months — which is part of why owners here often use their week at different times of year rather than sticking to one season.

Selling or Renting a Week Here

If you own a week at Wind in the Pines and are ready to move on, or just want to rent it out for a season, listing it privately is usually more cost-effective than going through a broker. On BidMyTimeshare.com, owners list their own week, set their own asking price, and deal directly with interested buyers or renters through the platform — there's a one-time listing fee and no commission taken from your sale.

Because Wind in the Pines is independently managed, resale isn't processed through a brand like Marriott or Hilton — it goes through the resort's own owners' association or management office. Before agreeing on a price with a buyer, it's worth asking the association directly for the current transfer fee and the latest annual maintenance fee, since these aren't published figures and can change year to year. Ask, too, whether the association holds a right of first refusal on resales, as some independent resorts do — this can affect how long a sale takes to close. A resale buyer typically takes on the week itself and the ongoing maintenance obligations that come with it, but won't inherit any RCI exchange history or banked points tied to the previous owner's account; exchange eligibility through RCI is generally established fresh once the transfer is complete.

Practical Notes for Buyers and Renters

Renters coming to Wind in the Pines are usually drawn by the Berkshires setting itself — proximity to Tanglewood, hiking, and a walkable downtown — rather than resort amenities alone, so it helps to mention nearby attractions and travel times in any listing. Great Barrington is about 2.5 hours from Boston and 3 hours from New York City by car, which makes it realistic for both weekend trips and longer stays. July, August, September and October are the busiest months thanks to the concert season and foliage, so weeks during those periods tend to attract more interest from renters, while May, June and September offer a quieter shoulder-season alternative with more flexible availability.