27,207 properties available

Located in New Marlborough, Massachusetts, United States. Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm. Newly renovated house in the Southern Berkshires on small horse farm. Huge kitchen, 5 bedrooms. Close to Butternut mountain, Garfield Lake, Great Barrington, Lenox, Tanglewood and Jacob's Pillow.We just finished a gut renovation of this property. The kitchen has a restaurant quality stove and tons of amenities. There is a fireplace, a deck and a lovely stream that follows the line of the property. Behind the house is a small barn with four horses. The house has 5 bedrooms, four bedrooms have queen sized beds and the fifth has a bunk bed with a bottom double bed and a top single bed double and a trundle bed. The other bedrooms have queen size beds. The house has a built with an interior cooling vent which keeps the house nice and cool during the summer. Air-conditioner on main level adds to cooling.Sorry! We do not rent the house for weddings or large events, we do not allow large parties at our house.

Located in Sheffield, Montana, United States. Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton! Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre property overlooking 200 acres of conservation land. Warm nights by the fire & scenic views all in our fully stocked home 8 min from Great Barrington. Within literal steps of Sunset Meadows Winery, walking distance of Big Elm Brewery & Berkshire Mountain Distillery. Peloton included. Pet-Friendly. Minutes to hiking, skiing, antiquing & moreSeasonal Hot Tub available May 15 until Oct 15*WINTER RENTALS (Oct 15 -May 15) SEE BELOW*

Located in Monterey, California, United States. Jaw dropping mountain & lake views in this stylish mountain home…. 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, 15 minutes to Great Barrington, 20 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.Great Room: Spacious open floor plan great for entertaining friends and family. Living room is furnished with 2 comfortable deep seated sofas, accent chair and 2 ottomans and 2 large coffee table’s, Relax and enjoy collection of movies on dvd players, listen to music on the stereo system or play games (we have a variety of board and card games).Family room (downstairs) with large sectional and daybed for extra sleeping. There is a TV and dvd player. Chef’s Kitchen: Stainless

Located in New Marlborough, Massachusetts, United States. Lake Buel Lakefront - 4 Bedrooms with private dock Idyllic Berkshire lakeside 4 bedroom cottage offering swimming, fishing, water sports and hiking.Located directly on the shore of Lake Buel in New Marlborough MA just minutes away from Tanglewood, Jacobs Pillow and many other attractions. Our family home boasts a 30 foot screened in porch for dining and enjoying the beautiful lake.All rooms are on one floor. You can drive right up to the front door. Great for older people or families with little kids.The Living room dining room combination is knotty pine finish with a 14 foot stone, wood burning fireplace (decorative only, not used for heating). The kitchen is fully equipped with a gas stove (built-in air fryer) dishwasher, microwave, toaster, refrigerator and coffee station. Included are linens and blankets, towels, cookware, dishes, an outdoor Gas BBQ grill with associated cooking utensils. The family room has a large sectional and a dining table that seats 8.This lake front cottag

Located in Glendale, Pennsylvania, United States. Peaceful Woodland Home in the Heart of the Berkshires The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails through the woods, a meadow, and a lovely babbling brook. Despite its secluded feel, the house just a short drive from many of the area's favorite attractions. The Residence provides a wonderful for base for enjoying all that the Berkshires have to offer, though guests may decide to spend much of their stay exploring the rustic beauty of the property itself.The house gets beautiful sunlight and has a fireplace and a deck overlooking the woods. The property includes a separate ping pong room that owners may access. Interested guests may inquire about use of the “The Office”, a studio space that can be used for writing, art, or meditation; with prior notice, this space can usually be made available as well.The house is conveniently located near many of the area's attractions, including the shops and restaurants of Great

Located in Lee, New Hampshire, United States. Mountain View Retreat w/ Hot Tub by Evergreen Home Exceptional VIEWS!! Take in the sunrise sipping coffee on the front porch & the sunset in the evening while relaxing on the back deck or soaking in the salt water hot tub. 4 bedrooms, beautiful eat in kitchen with those sunset views, gas fireplace & home gym. This location is perfect for exploring the Berkshires. Minutes from Tanglewood, Great Barrington, skiing, hiking, theatre. Wonderful restaurants, shopping, antiquing, golfing, kayaking are all close by no matter what experience suits you!If you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.Golden Hill Rd is a peaceful rural road with beautiful views and surrounded by farmland. Only 5 minutes to the center of Lenox, 10 minutes to the center of Lee and I-90.Guests will have private access to the entire home, and property.This beautiful country home has accessible features including show

Located in West Stockbridge, Massachusetts, United States. Secluded Mountaintop Retreat in the Heart of the Berkshires This secluded 6 acre property is just a 3 minute drive to the village of West Stockbridge. The house is set back from the main road at the end of a private .25 mile driveway that winds through a bird sanctuary, and uphill to the house. The house looks west to a beautiful Berkshires mountain crest.This light-filled house has a spacious 3,200 sq ft of living space spread out over two floors. The ground floor has a large living room with wood burning fireplace, formal dining area, kitchen, breakfast nook, master bedroom suite, and powder room. The second floor has two bedrooms, each with its own bathroom, and an open hallway with a cozy landing overlooking the front of the house. One of these two bedrooms is over 400 sq ft and has its own wood burning fireplace. There is a basement den and washer/dryer, and front and back patios with plenty of seating and a grill. Eclectic antique furnishings throughout the house make this a uniq

Located in Great Barrington, Massachusetts, United States. Stunning Renovated Victorian Located in the beautiful Berkshires, MA, the 5000 sqf home is located in a desired neighborhood known as "the Hill.” The sun filled house is on a quiet no outlet road and sits on 2.5 acres of landscaping including blueberry bushes, maple tree, lawns, mature flowers, and custom cobblestone. Connections to the Appalachian trail within 10 minutes. Lake Mansfield is a short 10 min walk. The Green River, with a swimming hole, is a 15 min hike through the woods. The Mahaiwe, a movie theater and the great thriving restaurants, boutiques, toy stores and coffee shops of downtown are a 15 minute walk. Tanglewood is a 20 minute drive.The house was built in 1910 and has been lovingly renovated and restored from the ground up. Many original details were restored to new condition (windows, radiators and the like) and modern conveniences added. There is central air conditioning, whole home audio system, movie room w/ mounted 65 inch 4k television, surround sound, double p

Located in Lee, New Hampshire, United States. Perfect Holiday Retreat, Completely Renovated, Central Location Our completely renovated farmhouse is set upon a hilltop overlooking downtown Lee. It is a perfect spot for culture, sports, relaxation, holidays and gatherings with family and friends. Take in the mountain / town views from the front wrap-around porch, or enjoy dinner and cocktails on the private back deck. The kitchen is newly renovated with granite counters, all new cabinets/appliances with a slider to the back deck and open to a charming sitting room. There is a formal dining room and a front family room with distant views. The new addition features a first floor master bedroom, bathroom with shower (also accessible from the hall) and laundry closet. The second floor has a newly renovated bathroom with shower and three bedrooms.

Located in New Marlborough, Massachusetts, United States. Sunset Falls: A Berkshire Mountain Luxury Retreat Welcome to Sunset Falls, where luxury meets nature in this modern architecturally significant home on 167 private acres. Open-concept living areas, floor-to-ceiling windows, and spacious great room. Breathtaking mountain views and full-service luxury amenities. Perfect for family gatherings and romantic getaways, this private oasis provides a serene escape, promising a unique, pampered experience with concierge service, ensuring a stay beyond the typical experience. Inside, the living room features floor-to-ceiling windows, allowing nature's beauty to seamlessly become a part of your surroundings. A curving roof adds a touch of architectural elegance, creating a haven of comfort and style. The great room and sunroom provide additional spaces to unwind and soak in the breathtaking views. Surround yourselves with nature while enjoying peace and serenity. BEDROOMS:Each bedroom in Sunset Falls is designed for ultimate comfort and tranquilit

Located in Becket, Montana, United States. Beautiful four season lakeside log home close to all Berkshires attractions. Very comfortable and private log home on a non motor lake. West facing (beautiful sunsets over the lake). Three bedrooms (two downstairs and master bedroom upstairs), two baths and a huge screened porch for lovely summer dinners. New in 2020 solar panels and AC upstairs and downstairs! Ultra fast fiber optic wi-fi. Wood stove. Music system with speakers inside and outside. Large lawn. Bicycle, kayak and canoe available. Walk down to the lake and go for a swim! Or go fishing! (catch and release)Close to all Berkshires attractions, only 5 minutes to Jacob's Pillow. Lots of hiking (Becket Quarry and Sanderson Brook Falls @ Chester-Blanford State Forest are nearby) and biking too. Legendary Dream Away Lodge restaurant 10 mins away.Available year-round. Very well equipped. No pets.

Located in Great Barrington, Massachusetts, United States. Contemporary 3-bedroom home with views, fireplace & close to Butternut Ski area Guests can take in the view from the front porch, and the house has plenty of space, including the basement game room and the backyard. The house has everything you need to enjoy Great Barrington. You are only one mile from the main street and the shops, restaurants, and bars.The large great room has seating for eight, a TV, and plenty of board games and puzzles. After a day of exploring the Berkshires, you can enjoy watching TV in front of the fireplace. There is a smart TV, so you can connect your streaming apps to enjoy your shows. You can also snuggle up under a blanket while enjoying the propane fire table on the front porch. The well-stocked kitchen has stainless steel appliances, granite countertops, and gas cooking. It also has all the necessary appliances plus a dishwasher, making cleaning up a breeze.The kitchen has all the cooking/serving necessities, including cookware, pots, pans, plates, cups,

Located in Great Barrington, Massachusetts, United States. Cozy escape in the trees of the Berkshires We are thrilled to share our country escape with you and hope you enjoy it as much as we do. Set on 5 acres of land, with an open backyard with a trampoline and trees surrounding you, our fully stocked home is true escape from the busy, over scheduled days of city life. We are a few minutes away from many wonderful, scenic hikes, a few breathtaking swimming lakes and skiing in the winter. Warm up by the fireplace after a long day outdoors or turn on the bbq for a delicious outdoor meal on the porch.

Located in Great Barrington, Massachusetts, United States. A spacious Log Home on 11+ Acres of Private Forest 5 minutes from Ski Butternut A private oasis on 11 forested acres on the backside of Butternut Mountain. Whether for skiing in the winter or hiking in the summer, our home is the perfect getaway. Our central location is ideal for experiencing all of the culture and nature The Berkshires has to offer. This well kept log cabin has five bedrooms, 2 full baths, an office, and basement with ping pong and laundry. There is a lovely porch with seating and sprawling green lawn. The cabin is set back far away from the road up a private drive. Ideally located, our cabin has easy access to the many sites and attractions the area has to offer..5 mi from the Appalachian Trail1.5 mi from Ski Butternut Resort4.5 mi from Downtown Great Barrington8 mi from Stockbridge14mi from TanglewoodDay trips to the Hudson valley (Hudson NY is only 45 min away), Mass MoCA, The Catskills, Williamstown, and Jacob's Pillow. Lastly, The Berkshires are a haven for lo

Located in West Stockbridge, Massachusetts, United States. Private Home on 17 acres 10 minutes to Tanglewood and other Berkshire Attraction Enjoy your stay in heart of the Berkshires! This 3 bedroom, 2 bath ranch vacation house in set on 17 private acres. Enjoy the sounds of nature while sitting on the private back deck sipping on coffee or enjoying a fire in the fire pit. This property is within walking distance to the Williams River - a perfect area to go swimming, fishing or a stroll.

Located in Stockbridge, Wisconsin, United States. Stockbridge Estate with Mountain Views Available for the week of LABOR DAY 2023. Completely reserved for June, July & August 2023. The estate is located a 5-minute drive from Stockbridge Village, 10 minutes to Tanglewood / Lenox, and less than 15 minutes to Great Barrington. This historic home has been lovingly maintained and offers a true getaway from the city, with a sweeping view of the Berkshire mountains. A heated pool, formal gardens, and acres of manicured grounds make at trip to this estate a perfect way spend the summer with family and friends.The home is meant for entertaining, with a large eat-in kitchen, enormous wraparound 3-season porch that is glassed-in with multiple entertaining and dining areas. There are 4 bedrooms and 5.5 bathrooms. 3 bedrooms have en-suite bathrooms and views of the the Berkshire and Taconic mountain ranges. There are multiple spaces to comfortably work from home. Formal living and dining rooms along with a library and family/TV room complete the

Located in Great Barrington, Massachusetts, United States. Serene Renovated Barn w/ Firepit About this spaceMinutes from downtown Great Barrington and at the top of a quiet property, this design-forward 1 bed/1 bath horse barn turned loft is the ideal getaway to enjoy all that the Berkshires has to offer. Explore the nearby hiking trails, boat on Stockbridge Bowl, swim in the Green River, shop and dine downtown, or ski at the local mountain resorts! At the end of the day, grill up some dinner, have drinks around the firepit, and stargaze from the lawn. Welcome to your perfect Berkshire escape!The spaceINSIDEAs you enter the barn on the first floor, you will find beautiful clapboard surrounding the dining area, which comfortably seats four. The kitchen and bathroom are also fully equipped with all the essentials for your stay. The coffee station includes a French press, locally roasted coffee, an electric kettle, and an assortment of teas for a slow morning.Upstairs, you will find the bright, open loft living room filled with natural light from

Located in Otis, Florida, United States. Nature retreat by Brook Long term rental November through MayThis Rustic contemporary cabin with barn beams/boards has a loft master bedroom suite with balcony views of the Brook & pines w/en-suite jacuzzi tub/showerfull bath downstairs and spare bedroom downstairs Bonus room: Den with wood stove heat has wrap around windows A huge custom fireplace in dining area w/a fully equipped kitchen w/pass thru windows & sliders that open to a spacious patio with views of Brook Seating area around fireplaceSkiing right down street in winter (5 miles away)& other ski resorts nearbyTanglewood, Jacobs pillow. arts venues aboundkayak on private beach/lake Amenities galore: heated pool, tennis, pickle ball, gym and hiking trails all within community Huge clubhouse with holiday events

Located in Great Barrington, Massachusetts, United States. Recently Renovated, steps to Lake Buel, close to Great Barrington & Stockbridge This charming and appropriately named "Little Cottage" was newly renovated in 2017. Enjoy a short walk (300 feet) down a dirt road to a small beach and private dock on Lake Buel, beautifully situated in the heart of the Berkshires. Experience new and contemporary furnishings in a country setting. Antiquing, rustic dining, skiing, hiking, theater and performing arts are only minutes away! Clay tennis courts on site. Great for families and outdoor enthusiasts or those that just want to unplug from it all.The cottage is just steps from the water where you can enjoy fishing, swimming, and boating on Lake Buel. There is a private community beach and dock. There is also a public boat ramp and parking lot just one street over. This Property is just a short walk from Camp Half Moon, a co-ed sleep-away summer camp for kids ages 6-16 that also offers half-day camps. Experience all the Berkshires has to offer.

Located in Otis, Florida, United States. Restored Historic Home Half Mile to Ski Resort! Escape to The Berkshires and explore endless adventures in the area’s mountains, forests, and arts venues! This 4-bedroom, 2-bath vacation rental lies within walking distance of Otis Ridge Ski Resort — a picturesque and family-friendly ski area — and offers all the modern comforts inside a classic-yet-updated living space. No matter the season you’re traveling, you’ll find fun adventures for the whole group with several lakes, state forests, and Jacob's Pillow dance venue a few minutes away.-- THE PROPERTY --Tax License: C0144032250 | 1,800 Sq Ft | Antique Heatilator Fireplace | Free WiFiBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin Beds | Bedroom 4: Full Bed | Additional Sleeping: 2 Queen Air MattressesINDOOR LIVING: Wood-burning brick fireplace (wood provided), historic furnishings & decor, hardwood floors, exposed beam ceilings, updated amenities, dining table, flat-screen TV, 2 shower/tub combosOUTDOOR LIVING: Back d

Located in Stockbridge, Wisconsin, United States. Berkshire Retreat- Stone's throw to downtown Lenox Berkshire Retreat - A stone's throw to downtown LenoxOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Privacy and peace abound in this beautiful Stockbridge home! Conveniently located about a mile to downtown Lenox and close to Stockbridge when you want to get out to the arts, explore, eat, play, and shop- you can The house is only minutes to Tanglewood, Shakespeare & Co., Kripalu, Great Barrington and the Stockbridge Bowl. In fact, the house has Stockbridge parking access! On days you would rather stay close to home, sit outside and soak in the sun from the home's spacious outdoor area. Surrounded by lush greenery and mature landscaping, this place is one of peace.Inside, the light-filled living room is cozy and kept warm thanks to the wood stove. Snuggle up while tuning into your favorite TV shows and movies. The adjacent well-equipped kitchen boas

Located in Great Barrington, Massachusetts, United States. Cozy Great Barrington Home ~ 1 Mi to Ski Resort! Art and history meet breezy mountain adventures at this Great Barrington vacation rental! This 4-bedroom, 2-bathroom house boasts a private setting, the comforts of home, and an ideal location 1.3 miles from Butternut Basin Ski Lodge. See the sights at the Norman Rockwell Museum, attend a summer concert at Tanglewood, or stop by the Naumkeag, a 48-acre masterpiece known for its elegant public gardens and historic home - all within 15 miles so you can make the most of your stay in the Berkshires.-- THE PROPERTY --1,650 Sq Ft | Dutch Colonial | Completely Remodeled | Outdoor Gazebo w/ Gas Grill (seasonal)Modern updates and comfortable accommodations make this exquisitely located home the ideal spot for your weekend getaway with friends!Main Bedroom: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Beds | Living Room: Full Rollaway BedINDOOR LIVING: 40-inch wall-mounted & gaming quality Smart TVs (in each bedroom)

Located in Lenox, New York, United States. Mid-Century Modern Berkshires Getaway on 6.5 Acres! Explore The Berkshires while staying in a beautiful mid- century modern deck house. Nestled within nature on a premier road in Lenox with 6 acres of woods that go to Lilly Pond in Stockbridge. Less than a mile from Tanglewood, downtown Lenox, Stockbridge Bowl, hiking trails, Kirpulau, the Mount and many other cultural institutions.

Located in New Marlborough, Massachusetts, United States. 1847 New Marlborough Farmhouse. a 4-BR home right in our quiet village. Our home is located in the beautiful village of New Marlborough - 15/20 min. from Gt. Barrington & Sheffield. The porch is where you will want to spend much of your time, overlooking cows grazing on the field across the street and wonderful sunsets. With its original wide floorboards, plaster walls and lots of light, there's room to spread out and enjoy yourselves.Walk to foot & drink at both the renouned Old Inn on the Green https://oldinn.com/ in the village center or Gedney Farm. The New Marlborough Preserve (paths + streams in the woods) is 200 yards down the road, The Farm New Marlborough https://thefarmnm.com/ is less than a mile with self-serve sustainably grown eggs & meats. Just past is the amazing Southfield Store (breakfast, lunch, some dinners).My wife and I have lived in the Berkshires since 1990. Raised our kids here. We moved down to this house from Lenox in November. Every summer we go up to Maine