Orlofseignir í Wood Creek Pond

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Rustic getaway in the beautiful Litchfield Hills of Northwestern Connecticut featuring a 2-acre pond and access to 9 miles of unique hiking trails on 450+ wooded acres. Cozy 1700's farmhouse comfortably sleeps 4 adults in 2 bedrooms, with an additional kids room that has a fold-out double futon and loft with one double air-mattress, perfect for children's sleeping bags. There is a pull out sofa in the living room. Dogs welcome! The house is next to Norbrook Farm Brewery, which you can walk to.

Rustic Pond Cabin: Nature, Stars & Serenity

🦉Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. All natural pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay n walk the trail around the pond, have campfires outside in firepit! Clean & no crazy rules! Surrounded by acres nature! Private-Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires!🦉

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

70’s Retro House

Reconnect with nature and loved ones in this familiar 70’s retro family-friendly place. Located in the Northwest hills of rural Connecticut. All seasons outdoor activities just minutes away. Hiking, mountain biking, disc golf, sport climbing, tennis, golf, pickle ball, skiing, snow shoeing and curling! Local live show and music theaters. Several local breweries. Two bedrooms and two full bathrooms. Kitchen, dining and sitting room with fireplace . Full use of yard, deck, fire pit and bbq grill.

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Waterfront oasis in heart of Berkshires

This house is a one-of-a-kind waterfront retreat that offers total privacy, spa-like serenity, and easy access to all the Berkshires has to offer. You'll find a fully stocked, professional-grade kitchen, a dining room perfect for family meals, and a living room with a wood-burning stove. There are two bedrooms downstairs and two upstairs. The house is close to skiing and tubing at Butternut, farm-to-table dining, shopping in Great Barrington and Lenox, Jacob's Pillow, and Tanglewood.

Grand View

Forget your worries in this spacious and serene space. Whatever your reasons for traveling you will find everything you need here. This is a great getaway but still not to far to enjoy the many amazing experiances the Berkshires has to offer. A beautiful 20 min ride to downtown Great Barrington will bring you to a variety of wonderful resturants and shopping. Or, maybe enjoy the theater, music or a movie. There is no shortage of hiking or exploring to be done. And the view is gorgous!

Retreat w 50 acre forest, waterfalls, tennis/bball

Perched above a brook in the woods. See the seasons fold and unfold in 50 acres of private forest, waterfalls, & pond. Fall asleep to sounds of the creek below. Wake to a canopy of beams, dappled sunshine, breakfast on a screened porch. Respite, creativity, and play (hike, sledding, 5 minutes from Mohawk Mtn Skiing). Hand built, inspired by Japanese teahouses, featuring tongue & groove construction, shoji screen doors, & tatami mats. Video: "Cornwall Hollow Teahouse" on YT or IG

Family friendly house with fenced yard & fire pit

Hillside Haus is a modern house close to Catamount Mountain & Ski Butternut and Hotchkiss School. Enjoy high ceilings, a cozy fire pit, fenced yard, family-friendly amenities (including crib and high-chair), and fully stocked kitchen. Sleeps 6 comfortably, and includes an office space. Perfect for year-round getaways—ski in winter, hike and picnic at nearby lakes and campgrounds in summer. Quick drive to charming and vibrant Great Barrington for shopping, art, and restaurants.

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.

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.

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.