Eastover Resort | My Family Travels
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Known for its adult retreats and Old World hospitality, this Massachusetts resort grants families their own special weeks.

Quiet and relaxing, tucked into the Berkshires of Massachusetts, near several metropolitan areas, Eastover has long enjoyed a special place in the hearts of vacationing New Englanders. Come summer, the resort fills with fishermen and golfers; come fall, with leaf peekers and seniors; come winter, with snowshoers. While adult-oriented for most of the year, during the holidays and other special periods Eastover loosens its collar, slips into jeans and welcomes all ages to old-fashioned outdoors fun.

In the Past

Originally built in 1910 by a wealthy stockbroker from New York City, this grand “cottage” was the summer home of his family of five, who were well taken care of there by a staff of 65 servants. After briefly becoming the Duncan School for Boys, Eastover was purchased by George Bisacca, who had emigrated to Danbury, Connecticut from Italy with his family in 1906. As a young man, Bisacca tried his hand at several businesses, and with hard work and ingenuity had amassed enough savings to embark on the adventure of developing a summer resort, originally intended for young singles.

His vision became a reality, and Eastover remains an informal recreational resort, open year-round, still operated by the Bisacca family. The singles have married and have had families, so the resort now caters, at specific times, to the entire Eastover Family of singles, couples and families with children. Adds owner Ticki Winsor, “We’re proud to say that we are celebrating our 63rd-year anniversary this year — same family ownership! In great part that is due to our ability to adjust to varying weather conditions and to the special needs and wishes of our guests.”

In the Present

Located on 1,000 acres of woodlands near Lenox in the Berkshire Hills of Massachusetts, Eastover Resort (413/637-0625; 800/822-2386) is a three-hour drive from New York City, two hours from Boston and one hour from Albany, New York. The emphasis here is on the casual and informal, and the mansion and surrounding cabins offer rustic but comfortable accommodations. All rooms are uniquely decorated and offer a variety of sleeping arrangements. Please note that there are no TVs in the rooms, only 50% have telephones and no liquor is served (though guests are welcome to bring their own). The dining room is informal for all meals.

In summer, enjoy the outdoor pool, mountain biking, hiking, and tennis. In winter, the indoor pool, downhill and cross-country skiing, and the toboggan run or, just relaxing and soaking in the natural beauty, will make for a pleasant getaway. When weather permits, the resort offers free alpine skiing for guests at Bousquets, about 5 miles away, and snowshoeing as well as cross-country skiing on the property.

In all seasons, the indoor pool, Kids Camp, nightly activities and dances for all guests keep guests entertained. If Mother Nature doesn’t cooperate with Eastover’s many outdoors pastimes, they adapt by arranging mountain hikes and trips to the nearby Norman Rockwell Museum. The quaint town of Lenox is fun to explore, as is nearby Hancock Shaker Village. And, don’t go home in summer without attending a performance at the Williamstown Theatre Festival or a concert at Tanglewood! 

For the Family

Only during the special Family Weeks or Weekends offered throughout the year, the resort becomes a playground for everyone. Families can choose to spend time together, participating in a wide variety of supervised games and sports, such as relay races, limbo contests, miniature golf and nightly movies. Daredevil relatives will like the toboggan slide that reaches 35 mph. The team sports are especially popular at family reunions, and Eastover does a good job helping reunion planners organize special meals and time together.

Alternatively, young kids (potty trained or accompanied by an adult) can participate in the daily Kid’s Camp Program, for morning, full-day or evening sessions, giving mom and dad some time alone. At day’s end, you can all join a Buffalo Safari to see the resort’s herd, try a hayride, or catch an evening movie.

Rooms and Rates

Eastover offers all-inclusive rates for family getaways that include accommodations and three meals a day, plus poolside dining, snacks and late night pizza. Please note that the resort does not have a liquor license, but you may B.Y.O.B. and the staff will provide juices, soft drinks and ice.

Also included is use of all resort facilities including free skiing and instruction in archery, golf and tennis. Extra fees are charged for ski and bike rentals and horseback riding; however you may bring your own bicycles, if you wish.

During 2009, rates are $116.50/N (midweek) or $129/N (weekend) per adult. Children under 3 are free, 3-7s pay $58.50/N, 8-12s pay $86/N and children 13 and over pay as adults. The resort has two suites available for larger families whose rates are 35%-50% higher than the standard rooms.

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This story was accurate when it was published. Please be sure to confirm all rates and details directly with the companies in question, and stay up to date with current events to ensure a safe and successful trip.