27,207 properties available

Located in Stephentown, New York, United States. 2 Bed Berkshire Getaway minutes to Jiminy Peak Ski Welcome to the historic Stephentown Hotel! Private apartment located minutes to Jiminy Peak Mountain in the world famous Berkshire Mountains! Right on the NY / MASS border in beautiful Stephentown. Surrounded by nature and serenity. Beautiful 2 bedroom apartment with a private entrance, completely renovated, new kitchen and bathroom, fire pit, BBQ and old fashion popcorn machine on site! Every stay includes water bottles, granola bars, oatmeal packets, coffee and tea! Parking in front.The apartment was renovated in 2023; brand new kitchen and bathroom. Large eat in kitchen with gas stove, dishwasher and Keurig machine. Bathroom features an incredible rain head shower, Bluetooth light / speaker in the shower to listen to your favorite music. (x2) Comfy queen beds, black out curtains and more. Private entrance and parking directly in front of the apartment. There is a fire pit with chairs and a BBQ. There is also an old fashion popcorn m

Located in Hancock, Florida, United States. Cozy couple resort style condo overlooks the beautiful Massachusetts mountains. A dream getaway. Perfect for a couple or family. Enjoy a late night swim and or a game of pool in the clubhouse. Wake up and enjoy a workout at the state of the art gym. Or simply enjoy the Mountain view from your room.

Located in Hancock, Florida, United States. Great Pet Friendly Condo at Jiminy Peak for all Seasons Beautiful condo at Jiminy Peak's Country Village. Two-bedroom condo with a full bath and laundry, completely renovated in 2022, including a new min-split a/c. Open living area for entertaining inside and deck for outside fun. Enjoy all of the amenities Jiminy Peak has to offer across all seasons. The condo is a two minute drive or eight minute walk to the base of the slopes and the main building, which has a small fitness room, game room and heated outdoor pool.Outdoor activities during the non-ski season include the mountain coaster, zip lines, giant trampoline and more.There is also a convenience store on the property that has everything you need from groceries to wine, as well great breakfast and lunch sandwiches.Many other great amenities close by, including golf, hiking, museums and Tanglewood.

Located in Canaan, New Hampshire, United States. Private home on a Beautiful lake. Large deck for entertaining Lakehouse 5 bedroom home. Steps from the lake. Large patiofor entertaining . New kitchen, Fully furnished. Washer and Dryer, Outside fireplace, Inside gas fireplace, Towels and bedding included. Hardwood floors, New Dock. Long private road leads to the house.

Located in Pittsfield, Wisconsin, United States. Cozy Berkshire cottage with fireplace. Relax at this unique, tranquil getaway. Minutes from all the Berkshires' offer; Tanglewood, Bousquet and Jiminy Peak ski resorts, museums, Colonial and Barrington Theater, Shakespeare and Co, Naumkeag, and many more. Conveniently located on the Pittsfield/Lenox line, close to many restaurants and shopping areas but tucked into the woods with hiking trails on the property. Our kitchen has all your cooking essentials. We have smart TV's and WIFI to relax with after your Berkshire adventures. The South Mountain House is a cozy one level with a nice open flow from the front driveway through the house to your own private back patio. Three bedrooms, one queen, one full, and one twin. The couch doesn't pull out but it's very comfortable. The house sits on 9.5 acres all for your enjoyment. There are cleared paths behind the house that you are encouraged to explore; from the patio, to the orchards, the fire pit to the boulders, there is plenty to

Located in Pittsfield, Wisconsin, United States. Large, comfortable house and yard located on a beautiful lake. Bring extended family or a group of friends to this great house with lots of room for fun, on a beautiful lake, just minutes drive from downtown Pittsfield. Spend time together in the open dining room & living room, play games, do puzzles, prepare meals in the large kitchen, watch TV (there are 4 TVs in the house). BBQ on the back deck and enjoy the large yard. In summer, swim & relax by the pool, & use the dock to take kayaks or a canoe out for a paddle. The house is a short walk from the town beach that has a public swimming area and a paved walking path along the beautiful lake. 20 minutes to Jiminy Peak. 15 minutes to Bousquet Mountain Ski Area. 25 minutes to Tanglewood. 35 minutes to Mass MoCA.

Located in Lenox, New York, United States. Historical Downtown 1bedroom Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for two, stainless appliances, and an array of cooking essentials. Provided are pots, pans, cooking utensils, glassware, flatware, dishes . The living room features a comfortable sectional and a flat screen TV for relaxing. Wi-Fi is available throughout the space. Central heat and air to provide a comfortable environment in any season. All linens and towels are provided.Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for two, stainless appliances, and an array of cooking essentials. Provided are pots, pans, cooking utensils, glassware, flatware, dishes . The living room features a comfortable sectional and a flat screen TV for relaxing. Wi-Fi is available throughout the space. Central heat and air to provide

Located in Hancock, Florida, United States. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone Summary:You want to pop out of bed, walk outside, and be right on the mountain - this is the place for you. This 1BR, 1BA Suite w Mountain Views features a king bed in the master bedroom that sleeps two, plus a second fold out queen sofa bed in the living room which sleeps an additional two. The Kitchenette comes complete with Keurig, Toaster, pots, pans, and more. The unit is equipped with games for those nights in, along w two TVs. As a guest, you have full use of all of Jiminy and the Inn, including yr round heated pool hot tub sauna, fitness center and moreAll of our deluxe rental suites, apartments, and condos are very different from the standard ones offered by mountain owners. Our accommodations are fully redone, privately cleaned, and all are RIGHT ON THE MOUNTAIN! Instead of dated lodgings, experience new furnishings, in-suite perks such as Keurig machines, air fryers, board games, plentiful

Located in Lenox, New York, United States. Luxury Berkshires Retreat in Lenox - Main House & Studio A private retreat in Berkshires set on 5 acres in prime location in Lenox - our all-season property offers secluded luxury whilst offering close proximity to Tanglewood, Ski slopes, hiking trails, Lakes, the historic town of Lenox and other Berkshire towns. Chic furnishings, eclectic artwork and modern amenities make this house the perfect spot to unwind in the Berkshires. You can rent the whole property for up to 15 people. There are two buildings on the property, the Main House sleeps 11 and the Studio sleeps 4.Main House [4400sqft]: This charming 1920s log cabin has an expansive layout with a breezeway connecting a newer section. Inside you will find five well-appointed bedrooms, three beautifully renovated bathrooms and a powder room. The heart and soul of the house is an expansive living room with a brick fireplace, furnished with stylish antiques and big comfortable sofas, a TV area, and a grand piano. Step out of the livi

Located in West Stockbridge, Massachusetts, United States. Enchanting Country House on 18 acres, Sunset Views,

Located in Hancock, Florida, United States. Family Friendly Townhouse in the Heart of Jiminy Peak Enjoy the Jiminy Peak Mountain Resort and explore the Berkshires during Spring, Summer, and Fall in this highly desirable Mountainside setting. This destination resort offers great off-season recreation. Some of the attractions include a Mountain Coaster, Alpine Slide, Trampoline Park, Aerial Adventure Park, Mountain Biking, Hiking, Scenic Chair Lift Rides, and 13 Nights. Guests can also enjoy 2 Outdoor Pools, Tennis Courts, Christiansen's Tavern, The Country Store, and more. Just a short drive from Jiminy Peak are even more Berkshire area events and attractions: first-class art museums - like Mass Moca and the Clark Art Institute - Ramblewild Adventure Park, the Tanglewood Music Center, Great Barrington, Williamstown, many fine restaurants, Mount Greylock, Pontoosuc Lake, and the list goes on...And yes, if you're here to ski or snowboard over Christmas or during February recess (our only Winter availability) - it's only a 2 minut

Located in Canaan, New Hampshire, United States. Berkshires Year-Round Home-Great mountain & lake views, sunsets, close to Lenox NEWLY RENOVATEDThis house has some of the most amazing views in the Berkshires, looking west over Queechy Lake; incredible sunsets and amazing fall foliage. Located 12 min from Tanglewood and Stockbridge Bowl, 15-40 min from summer theater and dance; 15-20 minutes from skiing, and close to museums and sculpture gardens. 15-25 minutes to Lenox, Stockbridge, Lee, West Stockbridge, Pittsfield, Chatham, HudsonExpansive wrap around decks on upper and lower levels. Heated endless pool built into a deck. Hiking, canoeing/kayaking and biking nearby.First floor: Living room with fireplace, kitchen, office, small bedroom, main bedroom suite, breezeway and 2-car garage. Powder room at entrance. There is a room off the entry foyer that may be used as an office/study or additional sleeping area as it has a pull-out couch. (Desk, printer, bookcase)Large main bedroom suite (Bedroom 1) with king bed and fireplace that ope

Located in Pittsfield, Wisconsin, United States. Lake View, Kayaks, Elec Bikes, Hot Tub, Large Open Great Room, Lrg Kitchen Families, couples, remote workers, and skiers, your Berkshires vacation rental search stops here! Bluescape is your place to reset and find calm with year-round lake views. Centrally located, start/end your outdoor or cultural adventure at this home away from home. Get more done at your distraction-free remote office with high-speed internet, including whole-home wifi with an option to be hard-wired. End each day with the quiet of the night while relaxing in the jacuzzi or by the fire table.Comments from previous guests:"Kristine’s house was perfect for our family ski getaway. It is very spacious and everyone was happy with their bedrooms and every common area. The massage chair and hot tub were huge bonuses after a day of skiing. Everything was clean and well-appointed. We will definitely be back!!" "This home was perfect! Very spacious for our family gathering. The house is much bigger than it appears! Huge li

Located in Lenox, New York, United States. The best of both worlds, Country and Culture 5 bed rooms, 3 full baths, large kitchen with a prep pantry. Master bedroom on the 1st floor, another master on the 2nd. En-Suite in the back of the house 2nd floor with a view of October mountain, the largest state park in Massachusetts. The house sits on the front of our 2-1/2 acre field, dotted with a few apple trees. 5 minutes from the bustle of downtown Lenox. 10 minutes from the great music of Tanglewood, all while in the country Go for a hike in the morning, catch a play at night, or go to one of the many museums for the day and have dinner at night at one of the many 5 star restaurants in town.

Located in Hancock, Florida, United States. Home in the Berkshires We are renting our 4 bedroom vacation house on 3 acres in the Berkshires for the summer/fall/winter. It has 2 master suites and 2 smaller bedrooms. Each bedroom sleeps 2. Other: 2. 5 baths, tv/play room with sofa, hiking in the back of the property, 10 minutes to a beautiful bicycling trail (Ashuwillticook rail trail), 5 minutes to skiing at Jimminy Peak and Ramblewild tree to tree adventure park. Farmers' markets, yoga, fishing, kayaking, hiking trails, antiques, farm to table outdoor dining.... etc everything that the Berkshires offer. A truly great place to get away from it all, relax and take long walks enjoying the secluded scenery. 2. 5 hours from Fairfield and Westchester Counties, 2. 5 hours from New York City, and 2:45 minutes from Boston. Please send me an email to discuss minimum stays. In the winter the house gets alot of snow and 4 wheel drive is required and snow tires are reccomended.

Located in Hancock, Florida, United States. Jiminy Peak Mountainside Getaway in the Berkshires This beautiful 3 bedroom, 3 full bath condo nestled in a quiet cul-de-sac is a short hop to the bunny ski lift! Newly renovated in Jan 2022, you will enjoy all new kitchen cabinets, appliances, countertops, flooring, vanities, toilets, & furniture. 2 living rooms, 2 TVs & extra amenities to make you feel at home. 2 parking spots in front of the condo, a ski locker & access to Jiminy's resort facilities(restaurants, pools, equipment rental, gym, ski shop) but removed from the busy crowds and noisy snow making machines. We're surrounded by trees making for beautiful scenery when covered in snow. Relax on the deck or by the fireplace with Netflix, Prime, etc. This is THE PLACE to come back to year-round!This spacious condo is the closest unit to the bunny lift (3 min walk)and the Doc Maynard pool in Hemlock Village. 2 bedrooms and a full bath are located upstairs. A mudroom, full bath, kitchen, living room and large deck are on the main f

Located in Canaan, New Hampshire, United States. One-of-a-Kind Breathtaking Berkshire Retreat 15 Acre One-of-a-Kind Luxury retreat with Close Access to Berkshires/Jiminy Peak with breathtaking views of the Catskill Mountains, all modern amenities in 3 bedroom, 4 bathroom extra-large living areas with 2 additional pull out couches for extra guests. Home is ideally located only 25 minutes to Tanglewood, Shakespeare & Co., The Mount, Norman Rockwell Museum. Close to Skiing, Hiking, golfing, shopping, museums & theaters or just to sit, relax and enjoy the views.

Located in Pittsfield, Wisconsin, United States. Ray of Sunshine Berkshire Home on Pontoosuc Lake Brand new construction directly on Lake Pontoosuc. This home sleeps 14 guests. There is a brand new chef’s kitchen! There are spectacular lake views from wherever you stand. A family room as well as an extra den/game room area. The house offers a side deck with a BBQ that gets sun all day long. There is also a shaded patio are in the back. But the icing on the cake is the bird’s nest on the top floor that looks out over the entire lake and has a outdoor fireplace. It is a really special spot. This home is available for renting Sunday to Sunday during the summer months.

Located in New Lebanon, New York, United States. Stone Villa: 20 minutes to Tanglewood This property is like nothing you've ever seen. After 2 years of renovation, we welcome you to the Stone Manor --a 150-year-old former Shaker workshop, now a modern home that combines 21st amenities with the historic past of a Shaker settlement. If you are interested in hosting a wedding here, please search The Ruins at Sassafras.The spaceThis house was the Shaker Brethren's Workshop where the Shakers packaged seeds. We renovated every inch of the house but retained the Shaker details: wide board pine floors, peg board, even the paint colors are those approved by the Shakers. The house is elegant, yet comfortable. Five en-suite bedrooms, a sitting room, family room, and professional kitchen abound with creative touches and overlook a pond, waterfall, historic ruins, meadows, woods, and perennial gardens. You'll never forget the spectacular views of the Lebanon Valley. We also offer the Caretaker's Cottage next door, which sleeps six. Guest accessYo

Located in New Lebanon, New York, United States. Sweeping Mountain Views in the Berkshires Mountain views in the Berkshires for every season! Country home in quiet neighborhood on 11 acres surrounded by farms. Perfect house for families! Enjoy a beautiful view of the Berkshire mountains while sitting out on the expansive deck or from bright and sunny sunroom. Enjoy the fenced in, heated, 20x40 inground swimming pool during the summer. Corkscrew Rail trail abuts the property offering 5 miles of flat, wooded trail perfect for biking, walking, running, exploring. Close to all the Berkshires has to offer! Discounts available for multi-week or longer term stays. Please send us a message! For holidays (thanksgiving /Christmas/ New Years) a Saturday night stay is required. For summer, bookings are for a minimum 7 nights, Saturday to Saturday.

Located in Lenox, New York, United States. Urban Peak Escape, Lenox, MA Discover Urban Peak Escapes in Lenox, MA—a charming New England town in the Berkshires. Just 1 mile from Tanglewood and Kripalu, our cozy rental is perfect for couples escaping city life. Enjoy breakfast at Haven Cafe across the street and explore downtown's shops and galleries. Hike scenic trails or visit Great Barrington (20 mins) and MASS MoCA in North Adams (40 mins). Immerse in culture with Shakespeare & Company and Jacob's Pillow. Relax in comfort with mountain views and modern amenities.

Located in Canaan, New Hampshire, United States. Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires 5 acres & a newly renovated 1 bed/1 bath cabin with a huge deck & screened porch overlooking a large pond. All you hear are bullfrogs, birds, train. Sleeps 4 with a full bed & queen pullout couch. Full kitchen has everything you need. There’s a charcoal bbq, 2 Midea AC units, Apple TV, Bluetooth sound bar, etc. Perfect if you need to write a book or just get away from it all. Great forest walks & trails surround the property. Pass to the members only swimming beach on nearby Queechy Lake available!One bedroom, dining/hang out room, screened in porch, large open kitchen/living room with large sliding glass door that goes to the massive deck with steps down to the pond. Fiber optic WiFi.The land all around the pond is cleared with a great hill and expansive lawn. The surrounding acres are great for exploring, hiking, finding a comfy spot to relax. Hiking trail abuts the land.5 wooded acres and hiking/walking

Located in Richmond, Utah, United States. Adorable Berkshires Loft on Quiet Dirt Road. Close to Tanglewood. Sweet loft on quiet dirt road. First floor has kitchen, eating area, living room, bathroom with laundry, three season porch overlooking private back yard, deck. Second floor is an open space with two sleep areas. One sleep area has a queen bed. The other sleep area has two twin beds. Quiet dirt road and pond to explore.

Located in New Lebanon, New York, United States. Beautiful 3 BR Berkshire Home - Mountain Views and Privacy on 10 Acres Beautiful, bright & clean 3 bedroom home is not a 'rental' house (we use it as our family ski house all winter). It sits on 10 acres and is very private. Has outstanding views, an enormous private yard (great for kids), and tastefully landscaped. The furnished screened in porch sits upon a very large wrap around deck to enjoy the views and beautiful summer nights in the Berkshires. There is a stream running along the entire property that is very relaxing to listen to at night. The proximity to the stream and woods also offers great exploring.Large open floor plan with living room and kitchen on first floor with an oversized stone floor-to-ceiling fireplace in the living room. All three bedrooms are on the second floor. The master bedroom has vaulted ceilings, master bath and a private deck overlooking the mountains.A large picture window that overlooks the property and mountains.Master Bedroom; king bed (2nd floor