Holiday rentals with a fireplace in Hancock

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!

Luxury A-Frame Cabin in the Woods with Sauna

🔨 Heads up: We’re currently making improvements to the property and there’s a chance of construction activity nearby on weekdays between 8am–4pm for the next few months. Evenings, nights, and weekends are completely peaceful and unaffected. 🏡 Modern A-frame in the Catskills with woodland views. Cedar barrel sauna, outdoor shower, smokeless fire table, and wrap-around deck. Queen bedroom with forest views, outdoor fireplace, fast Wi-Fi. Minutes to trailheads, waterfalls, and farmers markets.

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

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!

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.

Beautiful Jiminy Peak Townhome Family Friendly

Leave the city behind and come work remotely from our 3 bedroom, 2 bathroom newly renovated townhome. Whether you're visiting the Berkshires area in the winter for skiing at Jiminy Peak, or you're seeking summertime adventures on the lakes and the hiking trails, this 3 level home with puts you right in the middle of the action. Perfect for families, this rental is located in a community just a mile (3 minute drive) from the mountain and managed by Moresi Property Management.

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my cozy home sitting on 3 acres of land with in-ground saltwater pool. Enjoy the private, rural feel at this property with picturesque sunsets on the hills beyond. Under 5 min to Onota & Pontoosuc lakes, 15 min to Jiminy Peak & Bousquet ski resorts & a short drive to Lenox/Williamstown/North Adams. Light a fire in the living room & enjoy the ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

Lake House in Averill Park, NY

Our lake house is on Glass Lake in Averill Park, NY. In case you want to venture off, it is close to Saratoga (race season!), the Berkshires MA, Albany NY, and Vermont. Incredibly private with spacious property. Our lake house is great for families with kids and couples, and handicap accessible. It is great for any season (leaves, skiing, fishing, swimming). Kayaks, row boat.....and the lake!! Booking guest must be at least 25 years old.