What Guests Are Saying About Their Massachusetts Stay
“Our group of 11 had an amazing time. Plenty of room, everything we could possibly need was thought of, and it was so peaceful.”
“We had a lovely stay at the Butterfly Cottage! Perfect amount of space for four adults. We enjoyed spending evenings together by the fireplace. Perfect place in the woods but also not too far away from Lenox or Stockbridge. We hope to return again!”
“Everything was great! Highly recommend this place, very private, close to lots of great trails, and a very calming atmosphere.”
“Very happy with our stay. Peaceful, quiet, beautiful. Can only imagine what it looks like in later spring/early summer. Look forward to visiting again.”
“Our stay at the cabin was lovely! We were looking for a quiet weekend getaway and this fit the ticket perfectly. It was exactly as cozy as it was described in the listing and was the perfect size for two people. The large soaking tub in the bathroom was especially luxurious and relaxing. The communication about check-in and check-out was very clear. We are definitely planning to come back!”
Discover Massachusetts
The western edge of Massachusetts is where most travelers head when they’re after the full Berkshires experience: ski mountains in winter, world-class arts in summer, classic small-town main streets, and trails that turn into afternoon highlights. It’s a region that rewards a flexible itinerary and a few easy drives.
Winter weekends in the Berkshires are built for unhurried ski days. Jiminy Peak in Hancock is the largest mountain in the region and a strong all-around option for families and mixed-ability groups. Ski Butternut in Great Barrington is a long-running local favorite for relaxed days and learners, and Catamount sits right on the Massachusetts and New York border for an easy day trip. Most of our Berkshires vacation rentals put you within 30 minutes of all three, so a full day on the slopes still ends with a fireplace and a real kitchen waiting.
The Berkshires is one of the most culturally dense corners of New England, and a Massachusetts vacation rental is a great basecamp for it. Tanglewood in Lenox is the signature summer experience: the Boston Symphony Orchestra under the stars, picnics on the lawn, and a full season of pop and chamber concerts. The Norman Rockwell Museum in Stockbridge is worth a slow afternoon, and Jacob’s Pillow in Becket adds dance to the lineup. North in Williamstown, MASS MoCA and the Clark Art Institute round out a serious museum circuit, and Shakespeare and Company in Lenox keeps theater fans happy on cooler evenings. Most of our Lenox and Stockbridge area homes put you within 15 to 20 minutes of Tanglewood, so a 9pm encore still leaves time for a calm walk back to the porch.
For the outdoor reset, the Berkshires has the trail roster to back it up. Mount Greylock is the tallest point in Massachusetts and pays off a full day with summit views over four states. Monument Mountain in Great Barrington is the move when you want a shorter loop with a real overlook moment, and Bash Bish Falls on the New York border is the kind of waterfall stop that quietly becomes the highlight of the trip. The Appalachian Trail runs through the region too, with mellow day-hike sections near Cheshire and Tyringham for anyone who just wants a few hours in the woods.
Half the appeal of a Massachusetts trip is just driving between the towns. Lenox is walkable and lively, with bookshops, coffee, and a good restaurant on every block. Stockbridge has the storybook main street and the kind of slow, classic feel that makes you want to linger. Great Barrington brings more of an arts and food scene, while Williamstown up north pairs college-town energy with two of the best museums in the region. Several of our homes sit just a short drive from these centers, so a relaxed morning of browsing fits naturally between trail days and dinner reservations.
The food scene in the Berkshires is one of the quiet joys of a Massachusetts getaway. Brava in Lenox is a small, well-loved wine bar that locals will tell you about within five minutes. Around Stockbridge, The Red Lion Inn is the iconic stop for a polished dinner with deep New England roots, and Prairie Whale in Great Barrington is the go-to for a relaxed farm-to-table night out. For something low-key, the Marketplace Kitchen in Sheffield and No. Six Depot in West Stockbridge handle excellent breakfasts and casual lunches. With a stocked kitchen at your rental, it’s easy to alternate big nights out with simpler dinners cooked in, especially after a long day on the trails.