358,603 properties available

Located in Sandisfield, Massachusetts, United States. Waterfront oasis in heart of Berkshires This waterfront retreat offers total privacy and spa-like serenity. Steps from a private pond, it's also minutes from everything the Berkshires has to offer: skiing  at Butternut, dance at Jacob's Pillow, concerts at Tanglewood, farm-to-table dining in Great Barrington and Lenox, and much more. Outside, you'll find a furnished patio, perfect for watching the sun set over the water, and two firepits to gather around after dark. Inside is a fully stocked, professional-grade kitchen, a spacious dining room perfect for family meals, and a cozy living room and beautiful great room, both with wood-burning stoves. There are two bedrooms downstairs and two upstairs, and the house is fully equipped with everything you need to feel at home: fast wireless internet, washer/dryer,  microwave, toaster oven, coffeemaker and all the kitchen amenities, and canoes and kayaks for the pond.

Located in Becket, Montana, United States. Serene, Private Waterfront House --Perfect Summer Retreat! Enjoy everything the Berkshires has to offer from this beautiful, secluded, nicely renovated waterfront house set on two acres of forested land. Perfect for families or couples. Swim, fish, or boat from the backyard. (Canoe, Kayak and lifejackets provided.) Explore the stream that runs through the property. Picnic down by the water, or lounge on the deck. Make a fire in the fire pit and eat s'mores. Or just sit down by the crystal clear lake and listen to the sounds of nature while feeling the warm sun on your face. Very private--just one near neighbor. And if you want more activity, head to cultural activities such as Tanglewood, Jacob's Pillow Dance Festival, Shakespeare & Company; Mass MOCA, the Berkshire Museum, and Norman Rockwell Museum; historic homes such as those of Edith Wharton and Herman Melville; outdoor activities such as kayaking, canoeing, horseback riding, bicycling and hiking; and antiques and outlet shopping.

Located in Monterey, California, United States. Stunning Lakefront Berkshire Rental, Lake Garfield: private dock, boats, more Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, paddleboard, sunbathe, hike, bike, explore during the day. In the evening perhaps take a short drive to Tanglewood, Jacobs Pillow, Shakespeare & Co, or Mahaiwe Performing Arts, or to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the fabulous restaurants nearby, or have it at home as you watch the sunset over the lake. This private, modernized (major renovation completed 2018-19), 5 bedroom* cottage consists of two floors. The upper floor has a fully equipped kitchen , a large great room with a dining and living area, featuring a beamed cathedral ceiling, skylights, a dramatic fireplace, and an entertainment area with a wide screen TV. The dining room table seats eight and overlooks the lake. A transitional kitchen "island" seats an additional four. A screened porch overlooking t

Located in Monterey, California, United States. Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks Get carried away to this quaint 3-bedroom, 1-bath vacation rental in beautiful Monterey, Massachusetts. Surrounded by scenic landscapes, this cozy cottage is the perfect place to rest and recharge. Spend your days enjoying water sports from the private dock, hiking the Appalachian Trail, or taking a scenic drive to the town of Great Barrington. In the evenings, relax on the deck and fire up a feast. Immerse yourself in the natural beauty and serenity of the Berkshires at this delightful home!-- THE PROPERTY --MassTaxConnect ID C0467761930 | Walk to Private Boat Dock | Free WiFi | Washer & Dryer | Near Outdoor RecreationBedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Full Bed | Additional Sleeping: Pack ‘n PlayOUTDOOR LIVING: Spacious deck, screened-in porch, gas grill, dining area, 2 kayaks, beach towels, fire pit (wood not provided)INDOOR LIVING: Open layout, Smart TVs, breakfast barKITCHEN: Refrigerator, microwave, stove/oven

Located in Lee, New Hampshire, United States. Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood! Bright and airy, cathedral ceiling, Post & Beam home situated in the heart of the Berkshires, minutes from Lenox, Tanglewood, Stockbridge, Jacob’s Pillow, Mount Greylock, Rail to Trails, October Mountain, the Appalachian Trail, 5 different ski mountains, Great Barrington, antiquing and shopping, and the world’s best sweets at Peace, Love & Chocolate. Three minutes to Lee town center, 6 minutes to the Lee outlets, and 7 minutes to both Stockbridge and Lenox. With 4 bedrooms and a Bunk Room, the house can sleep 12 people in beds, and 14 including a pullout sofa bed. DescriptionFrom the moment you walk in to a wall of westerly facing windows full of afternoon sun and a Great Room with a 32ft ceiling, it is relax time. Comfortably furnished and well appointed with all the touches of home, you have multiple ways to relax indoors or out. You can flop down on either of the overstuffed club chairs or couch and put your

Located in Becket, Montana, United States. Wildlife Retreat in the Forest Home in the Birkshires! 12 minutes away from Jacob's Pillow, 2.5 hours away from NYC. Our Beautiful Lindal Cedar Contemporary home has everything you'll need. It is tucked away on a private 9+ acre estate with 4 large bedrooms, 2.5 baths. The Master Bedroom can be your own private getaway with 2 balconies. One overlooks the large living room with floor to ceiling windows and stone fireplace. The other overlooks the expansive property. It's definitely a tranquil place to rest and relax.One overlooks the large living room with floor to ceiling windows and stone fireplace. The other overlooks the expansive property. There is plenty of room. It's definitely a tranquil place to rest and relax.

Located in Becket, Montana, United States. Shales Brook Cottage Shales Brook Cottage is a newly renovated 2 bedroom and 2 bath, fantastic place. Vintage Malm wood burning stove for cooler nights. Central air. Screened porch and a deck that both overlook Shales Brook with serene sounds of water. Close to many fabulous Berkshire attractions. Light filled and stylish, you will enjoy everything this cottage has to offer.

Located in Great Barrington, Massachusetts, United States. NEW! Luxury GB home w/ heated pool less than 10 min from Butternut & Catamount Perfect location for summer, fall foliage, and winter skiing! A recently renovated home on 10 acres less than 10 minutes from downtown Great Barrington. With two primary suites with balconies, a heated pool, and a screen-in porch, you'll get ultimate privacy while also having accessibility to all the amazing things the Berkshires have to offer!Please reach out with any questions or if you'd like to discuss booking options.Two primary suites One suite on the lower level with sliding doors out to a private deck overlooking the pool areaOne suite on the upper level with a private balcony with sweeping viewsScreen-in porch overlooking pool areaBrand new three level oversized patio Heated pool*Built-in grill with barBuilt-in fire pitAttached garageCentral A/CUV light water filtration systemNote: propane for pool heat will be additional cost. Pool is open Memorial Day through Labor Day.

Located in New Marlborough, Massachusetts, United States. New England Family Home with Hot Tub and Pool Family-Friendly New England style 5 bedroom home located in the Berkshire hills, remote setting minutes from Stockbridge and Gt Barrington. Located on a quiet dirt road it is less than 3 miles from Gedney Farm and the historic Old Inn on the Green. This home offers a small in-ground pool, hot tub and a master bedroom with Jacuzzi bathroom. This relaxed setting is the perfect stay for long-term visits. High speed internet is available as of 5/1/21

Located in Great Barrington, Massachusetts, United States. Elegant Lake Buel Home Totally renovated and updated lake house with access to Lake Buel right across the quaint road. Sit on your large screened porch and take in the water view. Fiber optic cable installed for fast internet. Open plan living with a half bath on the first floor. 3 bedrooms and a full bath upstairs. French doors open to the modern, screened-in front porch. 5 minutes to Butternut Ski Area, 10 minutes to the center of Great Barrington and 15 minutes to Stockbridge. Also minutes to Bear Town State Forest and other trail heads for hiking. Close to all the local Berkshire sites and amazing restaurants (Cantina and Inn on the Green) just 5 minutes away.

Located in Monterey, California, United States. Cozy Lakeside Cottage Oasis Welcome to our charming lakeside cottage on Brewer Pond, the tranquil extension of Lake Garfield, with a neighboring standalone barn/rec room! If you're seeking a serene getaway with an array of outdoor activities, this is the perfect spot for you.Whether you're an adventure seeker, nature lover, or simply wish to unwind in a peaceful environment, our cottage has something special to offer for everyone.Stunning Lake Views: Start your day with breathtaking views of the shimmering waters right from the comfort of the cottage. Enjoy the stunning sunsets while sitting on the private deck or around the fire pit in the evenings.Water Activities: Embrace the wonders of Brewer Pond with our provided kayaks & canoes. Paddle along the peaceful waters, explore the hidden coves, and immerse yourself in nature's beauty. Fishing enthusiasts will find the pond teeming with various species to catch. Make sure to say hi when paddling past the local beaver lodge!Biking Advent

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.