Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

Bedroom 1: Full Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed | Bedroom 4 (Loft): Twin Bed with Twin Pullout (Can be converted into a King), Full Bed You'll find this rustic property hidden away in a semi-remote, wooded area, with very few neighbors nearby. Mornings here offer incredible views and quiet surroundings - best enjoyed with a warm cup of coffee on the deck. This property is located right on Round Pond. With crystal clear water untouched by busy beaches or motor boats, this lake is ideal for swimming and fishing! Take a dip off the dock, or venture out on the rowboat provided. After a day on the lake, head inside to enjoy some downtime. The living room is complete with cathedral ceilings, floor-to-ceiling views, and a cozy wood-burning fireplace, altogether creating the perfect place to unwind. End the day with a hearty meal made in the fully-equipped kitchen. Follow dinner with a sweet treat of s'mores by the outdoor fire pit! When you're ready to retire for the night, 4 bedrooms offer space for up to 10 guests.

Named as the #1 best place to live by Smithsonian Magazine, Great Barrington is a small-but-mighty town brimming with activities and charm. Take some time to tour the Berkshires. Within 15 minutes you'll be able to hike across Monument Mountain, shop and dine in Great Barrington, stop by the Norman Rockwell Museum in Stockbridge, or test your winning streak at the Springfield Casino just 40 minutes away. The famous Tanglewood lies just 10 miles away. Since 1937, Tanglewood has served as the summer home for the Boston Symphony Orchestra. Concerts here will take your breath away! The Berkshires turn into a winter wonderland when the snow falls. You'll find multiple mountains within 10 minutes of the property, including Ski Butternut and Catamount Ski Area, with Bousquet Ski Area, Jiminy Peak, and more just a short drive further!