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Highland Farm is a classic New England farmhouse set on rolling hills with sweeping pastoral views. With 6 bedrooms, a grand fireplace, and a classic barn, this spacious property is ideal for family reunions, retreats, and group celebrations.
"What a great place for a bigger group to gather! Plenty of bedrooms, with a nice in-law suite for those who like less noise at night. The kitchen was well equipped, and the outside is awesome!"
"I had the absolute best experience staying here. Lots and lots of space, a great pool and hot tub, fun games and activities. The hosts went out of their way to help us have the best experience. Absolutely would recommend!"
"Plenty of rooms for our entire family, including enough bathrooms for each family. The game room and hot tub were a big hit with our grandchildren, and the fire pit was so relaxing. We would love to visit again!"
Cheshire, MA
Lanesborough, MA
Looking for an intimate, beautiful setting for a small wedding or celebration? Several of our Berkshire Stream homes can be booked as a private venue for gatherings of up to 50 guests.
Exclusive use of the home and grounds for your event, spacious living areas, decks, fire pits, and stunning mountain and countryside backdrops for your photos.
Events are booked as an add-on to your stay, with a venue fee of $2,000-$2,500 in addition to the nightly rate. This covers the additional use, setup flexibility, and care required for hosting.
Tell us your dates, guest count, and what you have in mind, and we'll put together the details. Reach out through our contact details and we'll respond quickly.
Final event pricing and terms confirmed per property and date.
