Holiday houses in Dalton

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

Historic Stone Church in The Berkshires

<b>Hinterland Hall</b> was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Places in 1972. Ripe with history and impeccable beauty, Ian & Jane purchased the old stone church in May of 2021, completing an extensive restoration process in accordance with the Massachusetts Historical Commission. It is with great pleasure that we open our doors to you for a wondrous stay. <b>Follow us @hinterlandhall</b> Please inquire about weddings & events.

Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere

Welcome to Lake Ashmere! Our newly and completely renovated cottage features two bedrooms with comfy queen size beds, a loft with two full size beds, cathedral ceilings, a year-round six person hot tub and a large working kitchen stocked with everything you need. The living space is bright and airy. WiFi in the cottage is over 500 mbps, making it ideal for longer stays. The spectacular lake is just a three-minute walk from the cottage and has a kayak and inner tubes available to our guests.

Brooksong, the perfect Berkshires getaway

Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

Wildlife Lakeside Cottage; views/wildlife

Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. There is an incredible amount of wildlife, especially all types of birds. Sunny views abound. The house boasts a bright wood interior with a cozy feel. It has two and a half baths. There is a first floor queen bedroom with cathedral ceiling, and on the 2nd floor another queen room and a twin room-2 single beds.The adjacent lake teams with wildlife, seasonal weeds do grow. Contact us for conditions.

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Private Paradise in the Berkshires

Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.

1843 House - Bright and Airy 5 Rooms (2 Bedrooms)

Just bring your clothes and food! Everything else is here. Everything to cook with clean, shower, linens and extra blankets. Nice front and back porches. Plenty of parking. Centrally located in the beautiful Berkshires, a short drive to anything. The stairs are very quirky and not for the faint at heart. You'll love them or hate them! See picture. ***NOTE: We are family-friendly! We make an extra effort to ensure that children and pets feel welcome and are comfortable.

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Gorgeous Working Farm in the Berkshires

Get away from it all when you stay on our beautiful 4th generation working farm. Farmhouse backs up to 1000 acres of woodlands with trails, brooks and small bodies of water. See farm animals out grazing in the fields while you get cozy in our 5 bedroom farmhouse. Toast marshmallows over a campfire, walk the many roads and trails, or just sip some wine on the porch and enjoy the clean air and delightful views. Night skies are breathtaking on a clear evening.