Holiday rentals in New Marlborough

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

Stay in Downtown Canaan

This light-filled space is in a separate wing of my house with its own private entrance. There is one bedroom with a king-sized bed, spacious living room with table for meals, a large TV, a refrigerator/freezer stocked with bottled water and 1/2&1/2 for coffee, microwave and coffee maker with coffee pods are provided. You will hear the train as it travels through town. There are several places to eat nearby. Be sure to check out GUIDEBOOK on my listing to see what our area offers!!!

Converted Berkshire schoolhouse on a quiet river

Renovated schoolhouse on a quiet river in the Berkshires. This is the perfect place to unwind. Great for families and friends to relax and reconnect. Take a walk to the waterfalls, play croquet on the lawn, gather dinner from our seasonal garden and enjoy 'smores around the fire pit. Very private and woodsy, but close to Butternut for skiing, Great Barrington for shopping and access to all the music and art the Berkshires has to offer. Home is stylish, comfortable and inviting.

Belle Meade

Open concept home with a Zen feel and made for relaxation. Nestle into the covered porch and spend hours of peaceful contemplation with nature all around! When you’ve had enough recharging, plan a backroad trip to endless possibilities. Tanglewood and Jacob’s Pillow are nearby via beautiful country roads. There are hikes for any level. Great restaurants, farmer’s markets and Guidos gourmet market just minutes away. Eat out or stay in with a cook’s kitchen and grill deck.

Berkshire Treehouse Retreat

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

A luxurious farm hideaway in the treetops

Want to get away to your own private hideaway, overlooking rolling hills and a pastoral farm? The space is small but luxurious, with a well-equipped kitchen, a comfortable bed with high-end 100% cotton linens, lots of soft throw blankets, real leather furnishings, and a marble-tiled bathroom. The views from the deck are stunning. Plenty of hiking spots, fine dining, and cultural sites nearby. Or just lounge by the pool (Memorial Day through Labor Day)

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Berkshires Cabin in Woods with Mountain Views

A private hilltop Berkshires cedar cabin nestled amongst beautiful woodlands. Unwind with breathtaking mountain views from charming double balconies. Gather on the serene screened-in porch for meals. Get cozy with s’mores by the fire at night with an unobstructed view of the stars. Head to nearby Great Barrington for dinner. This is a perfect getaway to relax in peace and quiet and connect with nature, family and friends.