Tranquil vacation homes for a getaway in the Berkshires of Massachusetts

If you're looking to escape the crowds and enjoy some peace and privacy this year, vacationing in the Berkshires in western Massachusetts might be a perfect fit. For those who seek a socially distanced getaway, this rural region in the mountains will delight.

There are plenty of outdoor activities, antiques, a rich arts scene, and all the farm-to-table food you could want. And there's no bad time of year to visit the Berkshires! Enjoy skiing and ice skating during the winter, annual festivals including the Boston Symphony Orchestra’s residency at Lenox’s Tanglewood Music Center in the summer, and stunning fall foliage in autumn. Positioned between New York and Boston, the Berkshires area offers scenic countryside mixed with culture and art.

Find a home swap in the Berkshires for a vacation where you can truly unwind and be at peace in nature.

Huge designer home exchange in Lenox, MA

Escape city quarantine in this designer retreat surrounded by woods, the perfect place for a family or group of friends to relax and get away. The home is beautifully furnished, has comfortable beds, sunroom, fireplace, movie system, and more. Just bring your toothbrush and enjoy your peaceful, relaxing getaway.

"We thoroughly enjoyed meeting Tatyana and her family. It was what HE is meant to be meeting pleasant people that you appreciate and become your friends. We will plan a visit to their home in the future...for sure." -Raul and Miriam

Tranquil mountainside sanctuary in Great Barrington, MA

This beautiful home in the Berkshires is built into a steep, secluded, forested mountainside with a stunning view. Your only neighbors will be the local wildlife! The stocked pantry, endless kitchen appliances, in-home entertainment, and nearby attractions will keep the whole family content during your getaway.

"David's home is even better than the pictures suggest. It's immaculately clean and organized, and equipped with everything you'll need for a great trip to the Berkshires. The area is wonderful—charming main streets, great restaurants, and excellent hiking. David was helpful and responsive through the whole process. We would definitely stay at David's home again." -Brian

Spacious, modern home in the Berkshire Mountains

This custom post and beam house was just completed in 2020 and is set on nearly three acres. A creek runs through the property and there are hiking and ski trails right out the back door, making this retreat a nature lover's paradise. The rural location means your family will have total privacy in this gorgeous home.

Charming cabin in the Berkshires

This cozy four-bedroom home is in the heart of Southern Berkshire County, close to skiing, the town beach, and great restaurants. The home features all the amenities a family could need, from a farm table kitchen to a rocking chair front porch. Use this home as a launch pad to explore all the best attractions in the Berkshires, or just enjoy the peace and quiet in this welcoming home exchange.

Historic 1770 home on 12 acres in the Berkshires

This beautiful 1770 home is located on 12 acres of fields, woods, gardens and fruit trees bordered by a mountain stream. There is plenty to do, including ping pong, foosball, a pool table, and hot tub. For a slower pace, just enjoy eating al fresco on the patio or reading on the hammock beneath the apple trees. The home is in a quiet, private setting but just eight miles from the center of town.

"It is a really unique, beautiful home with tons of character. Their property was just beautiful, and our children particularly enjoyed checking the chicken coop for eggs and picking apples from the many trees throughout their property. We came home to a spotless apartment that was just as clean (if not cleaner!) than we had left it. We had a great weekend getaway and would exchange with them again in a heartbeat." -Kim

Charming Berkshires home ideal for ski lovers

This cozy vacation home is close to local ski resorts during the winter and outdoor and cultural offerings in the summer. It sits on 4.5 private acres, with a fully finished basement and screened porch that overlooks the beautiful yard. Guests can choose to stay in and cook using the home's stocked kitchen and outdoor grill, or eat in one of the many excellent restaurants in town.

Spacious Victorian house in the heart of the Berkshires

This spacious Victorian home is situated in a tranquil small-town neighborhood in the southern Berkshires. It has a spacious deck that overlooks flower and vegetable gardens, and a terrace perfect for entertaining. The comfortable family home is full of books and surrounded by beautiful trees. You can truly unplug and get away from it all in this charming home and peaceful neighborhood.

"We had a wonderful family reunion at Karen's home in the Berkshires. It was cozy and comfortable. We enjoyed walks into town and also just hanging around the house playing board games. It was a great house for a large group and especially for the three kids with us." -Bette

Charming country home in the Berkshires

This beautifully renovated barn on 3.5 acres sits on a quiet, secluded road where you will have total peace and privacy. Sit on the screened in porch and enjoy the landscape and gardens, spend the day bird watching, swimming or hiking, or tour all the Berkshire attractions— art, music, culture, swimming, hiking, skiing, and incredible dining.