27,207 properties available

Located in Pittsfield, Wisconsin, United States. Stylish cottage located by Pontoosuc Lake with lake views! Kick back and relax in this French influenced, stylish cottage located in one of the best Pontoosuc Lake neighborhoods there is. You'll be walking distance to the lake for all winter activities including snowmobiling, cross country skiing, skating and ice fishing with a few ski mountains all under 10 miles away. When you return, warm yourself up in the hottub by the rustic firepit that's built for some serious heat.

Located in Lanesborough, Massachusetts, United States. Charming Apt in 18th c Berkshire Farmhouse Enjoy the Berkshires while staying in a historic farm house minutes from Jiminy Peak Ski Resort, walking distance to coffee and breakfast, and at the base of Mt. Greylock. In the summer enjoy blueberry, raspberry, and flower picking from our (Second Drop Farm) beautiful fields. Wander our walking trails or take a dip in our private creek. In the fall, enjoy the best fall foliage New England has to offer. And in the winter take a drive down the road to Jiminy Peak and enjoy some skiing!

Located in Hancock, Florida, United States. Snowdrop Lodge - Beautifully Renovated Condo Beautifully renovated berkshire condo within Jiminy Peak grounds. Corner unit with ample parking, only a short walk to ski slopes and steps away from community pool. You’ll also have full free access to Jiminy’s facilities including their year round heated pool, hot tubs, sauna and gym. The master bedroom has a full bathroom, and the kitchen/dining area is fully quipped and opens into a spacious living room with a fireplace and a work area. Another bedroom and half bath complete the unit. The unit has a washing machine/ dryer and has a private deck to enjoy the beautiful mountains. Want an adventure? Hop in your car and in under 5 minutes Ramblewild awaits, offering tree to tree adventures for all skill levels. We think you'll find the condo a wonderful base to enjoy all that the Berkshires has to offer, not only during ski season, but all year long!

Located in Hancock, Florida, United States. Close to Jiminy Peak! Wyndham Bentley Brook 2 Bd. dlx. Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent choice for rest and rejuvenation. Well-known for its family-friendly environment and proximity to great restaurants, Wyndham at Bentley Brook makes it easy to enjoy the best of Hancock. Rooms at Wyndham at Bentley Brook offer a flat screen TV, air conditioning, and a kitchenette providing exceptional comfort and convenience, and guests can go online with free wifi. Whether you're traveling for business, pleasure or both, Wyndham at Bentley Brook is sure to make your visit to Hancock one worth remembering.Items to note: * The bed sizes/layout can vary within this unit style. * Closest shopping/entertainment/additional dining: 30 minutes away * Closest nightlife is in Albany, 45 minutes away * Vehicle recommended to enjoy area KOALA Disclosure Summary:*IMPORTANT: Payments appear as “KOALA VACATIONS” on credit ca

Located in Hancock, Florida, United States. Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More! Dreaming of waking up, heading downstairs, and being right on the mountain? This is the place for you. Conveniently located near all area hospitals, yet packed with fun amenities on-site, this 1BR 1BA Suite is nestled right within the Country Inn of the Year-Round Jiminy Peak Mountain Resort. Enjoy all the convenience without the bustle—there's nothing better.This super comfortable 500 sq ft condo features a King bed in the master bedroom that sleeps 2, plus a pull-out sofa bed in the main room that sleeps another 2—perfect for guests or family. The kitchenette in the suite provides a stovetop, along with an air fryer, microwave, toaster, and all necessary cookware. A Keurig Machine is included for your morning coffee. Everything is brand new.The bathroom comes stocked with an opening supply of organic shampoos and soaps. For cozy nights in, enjoy a variety of board games and cable smart TVs with all your fav

Located in Hancock, Florida, United States. Wyndham Bentley Brook-Ski In/Out, Pool, Next to Jiminy Peak - Only 25% Deposit! *Vrbo is currently experiencing technical issues related to displaying accurate information under “Rooms & beds.” The correct information associated with this listing is as follows:(1) king-size bed in the primary bedroom(2) double-size beds in the guest bedroom(1) queen-size sleeper sofa in the living area(2) full bathroomsWHAT YOU’LL LOVE:Nestled among the Berkshire Mountains, you will find a true New England treasure; Wyndham Bentley Brook. Located a mere 200 feet away from the premier Jiminy Peak Mountain Resort puts you in position to take part in the area’s best skiing and snowboarding. After a full day on the slopes, warm up and relax in a cozy studio, one- and two-bedroom units. Rooms here showcase both scenic mountain and valley views, and are filled with all the comforts and conveniences of home. All units feature a full kitchen, equipped with a stove, oven, dishwasher, microwave, and all the coo

Located in Pittsfield, Wisconsin, United States. Apartment Newly Remodeled Super Location Large 2nd floor fully furnished apartment in 2 story corner house with plenty of parking and separate back entrance/staircase. Eat in Kitchen with all new appliances including a washer and dryer. Freshly refinished hardwoods throughout and new kitchen vinyl planking. All new furniture and bedding including area rugs. An additional bonus room that can be used as a sitting room or study. Plenty of closet and storage space. Large covered porch off the living room. Downtown Pittsfield Is 2 miles. Close to lakes and 5 minutes from Bousquet ski area.

Located in Hancock, Florida, United States. Outside Adventure-Skiing, Hiking, and Relaxation Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent choice for rest and rejuvenation. Well-known for its family-friendly environment and proximity to great restaurants, Wyndham at Bentley Brook makes it easy to enjoy the best of Hancock. Rooms at Wyndham at Bentley Brook offer a flat screen TV, air conditioning, and a kitchenette providing exceptional comfort and convenience, and guests can go online with free wifi. Whether you're traveling for business, pleasure or both, Wyndham at Bentley Brook is sure to make your visit to Hancock one worth remembering. Items to note: * The bed sizes/layout can vary within this unit style. * Closest shopping/entertainment/additional dining: 30 minutes away * Closest nightlife is in Albany, 45 minutes away * Vehicle recommended to enjoy area KOALA Disclosure Summary:*IMPORTANT: Payments appear as “KOALA VACATIONS” on credit card st

Located in Pittsfield, Wisconsin, United States. Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield! New listing ! Looking for a centrally located place to stay? This Berkshires home is 5 minutes from Bousquet Ski Resort , 20 minutes from Jiminy Peak, and minutes from hiking and museums.Tanglewood in Lenox only 15 minutes away. Hang out on the deck, play yard games and cook out on the grill with friends and family.

Located in Hancock, Florida, United States. Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn Summary:You want to pop out of bed, walk outside, and be right on the mountain This 1BR 1 BA Ground Floor Unit Charming Mountain Yeti Decorated Suite right by the entrance features a king bed in the master bedroom, plus a fold out queen sofa bed in the living room. The kitchen comes complete with all your needs, incl Keurig, pots, pans, etc. The unit is equipped with board games , along with cable TVs that have all your favorite shows . The Inn amenities are yours including heated year round poolThe Space:This suite is fully redone, with new furnishings, kitchenette, beddings, linens, etc. All 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, a

Located in Old Chatham, New York, United States. Mountain View Retreat in Hudson Valley near Berkshire Attractions Sweet guest cottage perfectly located for exploring Columbia County, the Berkshires or simply lazing on the lawn with a lemonade and a good book.Totally renovated in 2019, the cottage has an open layout with kitchen, living room, dining area and 2 bedrooms. It's set in a sunny, open meadow surrounded by woods with views of the Berkshire mountains. Walk down a grassy path to a bass filled pond complete with an ancient dock. For hiking, there's a spectacular conservation area a mile down the road.The kitchen is designed for people who love to cook with all new appliances including dishwasher, stove, oven, refrigerator, microwave andcoffeemaker. Central AC and heat, W/ D, WiFi and TV with an Amazon Firestick. Feel free to walk anywhere on the 9-acre grounds. On weekends we stay in the Main House up the dirt road. You can always explore Chatham’s wonderful restaurants, cafes, bookstore and brewery only 9 min. drive. Also we

Located in East Nassau, New York, United States. Get away and get back to nature! Connecting with nature doesn't mean you have to rough it. The Owl's Nest is a cozy campsite located in the heart of the Berkshires. 32 acres to explore and wildlife to watch. There is a hawks nest on the property and if timed right you can watch them hunt the field. Please also view , The Hawk's Nest & The Owl's Nest. All the same features but each are unique.Disclosure: We are a couple miles from Lebanon Speedway and some of the races can be loud. Extremely quiet otherwise.

Located in Hancock, Florida, United States. Mountainside Wyndham Bentley Brook! 2 Bd. dlx. Everyone needs a place to lay their weary head. For travelers visiting Hancock, Wyndham at Bentley Brook is an excellent choice for rest and rejuvenation. Well-known for its family-friendly environment and proximity to great restaurants, Wyndham at Bentley Brook makes it easy to enjoy the best of Hancock. Rooms at Wyndham at Bentley Brook offer a flat screen TV, air conditioning, and a kitchenette providing exceptional comfort and convenience, and guests can go online with free wifi. Whether you're traveling for business, pleasure or both, Wyndham at Bentley Brook is sure to make your visit to Hancock one worth remembering. Items to note: * The bed sizes/layout can vary within this unit style. * Closest shopping/entertainment/additional dining: 30 minutes away * Closest nightlife is in Albany, 45 minutes away * Vehicle recommended to enjoy area KOALA Disclosure Summary:*IMPORTANT: Payments appear as “KOALA VACATIONS” on credit card stat

Located in Hancock, Florida, United States. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn Summary:This is the MOST UNIQUE suite in the Berkshires, specially designed for an incredible experience. The Master Bedroom Features a King Bed, and the main room has a Queen Sofa bed for extra room. This Peaceful Suite features a luxurious massage chair, waterfall, color changing lights, Ionic Salt Diffuser, Zen Garden, and tons of surprises you just have to see. There is even a professional massage table in the closet! The King BR comes with Oil Diffuser, Sound Machine, Bamboo bedding.The Space:The entire place is geared toward tranquility and fun. Your suite is center mountainAll 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, boa

Located in Lenox, New York, United States. Enjoy a renovated private home right in downtown Lenox Our lovely home is literally a stones throw from Lenox's downtown shops and fabulous restaurants but also in a very quiet neighborhood. A newly renovated 100 year old home with historic charm but with all the immensities of of 2018 ! Exactly 1.1 miles to Tanglewood's front gate which makes for a wonderful summer stroll to the venue without dealing with traffic.3 BR's on the 2nd floor, (2) lovely porches, front & back. The front is fully enclosed with screen windows, the back open and airy under a roof cover. Lovely back yard with fireplace, gardens and serenity, A MUST SEE !!

Located in Lenox, New York, United States. Lenox Retreat Near Tanglewood, Including Rescued Mini Donkeys! Our property is a renovated 1770s stage coach stop. The upstairs of our home (with separate entrance) is our rental apartment space which is hotel style, meaning 2 big bedrooms, a big common area, a nice big bathroom, and some basic appliances (mini fridge, microwave, and coffee pot). Washing dirty dishes in our bathroom is not allowed. Paper goods will be supplied. We encourage folks to eat out, pick up food, or have food delivered. Local restaurants -Antimony, 110 Grill, Mazzeos, Jae's, Bousquet's The Lift, Alta, Brava, Heritage Tavern, Balderdash Winery, Haven, Lenox Coffee, Betty's, Zinc, Firefly, Boema Pizza, the Locker Room, Vongs, and Frankies to name just a few. There are many old Inns that also have bars and restaurants. Balderdash Winery and Antimony are amazing places that have live music on the weekends!There is a community meditation field, roughly 20 acres, across the street for walking or meditating. There

Located in Hancock, Florida, United States. SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2 This ski-in, ski-out condo is located right at the base of the mountain in JJ’s Lodge in the heart of the village at Jiminy Peak. Unmatched access to all of Jiminy Peak’s year-round activities. Skiing, mountain biking, hiking, tennis, swimming, fall foliage leaf peeping, shops, restaurants and the Mountain Adventure Park including the famous Mountain Coaster, Alpine Super Slide, Euro Bungy Trampoline, Soaring Eagle, Giant Swing, and climbing wall.Experience all the Berkshires have to offer with swimming, boating, and water skiing on nearby Pontoosuc Lake, Donnybrook Country Club with 18-hole golf course open to all, historic Lenox and Stockbridge, Tanglewood, summer stock theater festivals, and more. This two bedroom, two bath unit with porch overlooking the mountain sleeps 9 and is perfect for one large family, two families, or three couples. Large, fully equipped kitchen has everything you need to make yo

Located in Hancock, Florida, United States. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count Summary:Welcome to the Woodlands. This unique Suite lies right on Jiminy Peak Mountain within the Country Inn. 1st Floor, mountain views, private parking in gated lot on Jiminy. No detail was missed in this adorable 1BR 1 BA Suite which Sleeps 4 comfortably with its King Bed and Pull out Queen Sofa in main room along with Kitchenette and Full Bath. Located in the BEST location At Jiminy - The Country Inn at the base of the mountain, you need to see this suite to believe it.The Space:The most unique Suite in the Berkshires - This gorgeous woodland Themed Hotel Room will bring forest magic to your summer retreat or Ski Getaway. No detail was missed in this adorable 1BR 1 BA Suite which Sleeps 4 comfortably with its King Bed and Pull out Queen Sofa in main room along with Kitchenette and Full Bath. Located in the BEST location At Jiminy - The Country Inn at the base of the mountain, you need to see thi

Located in New Lebanon, New York, United States. Historic New Lebanon Hideaway on 33 Private Acres! Get the cozy bed and breakfast feel all to yourself at this New Lebanon vacation rental. This sprawling home with 5 beds, 3 full baths, and 2 half baths at the base of the Berkshires still has all of the charm from its construction in 1790 and then some! With multiple sitting rooms and 33 private acres of lush landscape to explore, the whole crew will find relaxation at this beautiful retreat. Visit historic sites and museums, hit the ski slopes, or simply enjoy the views from the deck.-- THE PROPERTY --Jetted Tub | On-Site Pond | 8 Mi to Ski Area | 3,600 Sq FtBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Twin Bed | Bedroom 5: 2 Twin Beds | Loft: Full Sleeper SofaINDOOR LIVING: Flat-screen TV, board games, fireplace, WFH workspace, dining table, en-suite bathroomOUTDOOR LIVING: Private acreage, deck, dining areaKITCHEN: Cooking basics, dishware/flatware, dishwasher, refrigerator, stove, microwave, coff

Located in Hancock, Florida, United States. SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1 This ski-in, ski-out condo is located right at the base of the mountain in JJ’s Lodge in the heart of the village at Jiminy Peak. Unmatched access to all of Jiminy Peak’s year-round activities. Skiing, mountain biking, hiking, tennis, swimming, fall foliage leaf peeping, shops, restaurants and the Mountain Adventure Park including the famous Mountain Coaster, Alpine Super Slide, Euro Bungy Trampoline, Soaring Eagle, Giant Swing, and climbing wall. Experience all the Berkshires have to offer with swimming, boating, and water skiing on nearby Pontoosuc Lake, Donnybrook Country Club with 18-hole golf course open to all, historic Lenox and Stockbridge, Tanglewood, summer stock theater festivals, and more. This three bedroom, two bath unit with porch overlooking the mountain sleeps ten and is perfect for one large family, two families, or three couples. Large, fully equipped kitchen has everything you need to ma

Located in Lanesborough, Massachusetts, United States. Lakeside Berkshires Home Near Hiking & Skiing! Escape to the Berkshires for a peaceful mountain respite at this charming, rustic 3-bedroom, 2-bath lakeside home. Choose to enjoy music at Tanglewood or swim in Pontoosuc Lake, then relax on the neighborhood beach after a day packed with adventures. Come autumn, soak in the vibrant foliage on trails and lookouts. In the snowier months, pay a visit to nearby Jiminy Peak. With everything this homey Lanesborough vacation rental has to offer, the perfect weekend getaway or family vacation awaits!-- THE PROPERTY --C0289563456 | 2,327 Sq Ft | Lake Views | Family & WFH FriendlyEnjoy scenic views overlooking Pontoosuc Lake and light-filled spaces at this quaint family home, providing a relaxing retreat from the business of everyday life, while still maintaining a close proximity to all the Berkshires hottest attractions.Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed | Living Room: Futon | Additional Sleeping: CribHOME FEATURES:

Located in Hancock, Florida, United States. Huge Beautiful House-2 families-16 Acres -Low rates- 2 min from Jiminy Peak 2 MIN TO JIMINY PEAK - right down the road! Close to Lenox and Williamstown! Reduced rates. Great for 2 families (max 8 persons! Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 2 minutes from Jiminy Peak, 15 min to Williamstown and 30 minutes to Lenox!! Book now!!! House comfortably fits 2 families with small children- see reviews With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy feel. Each one of the 3 large bedrooms has walk-in closets and beautiful new furnishings. The master suite has a king size bed and matching furniture with a 50” Samsung LCD HDTV. The attached master bathroom has a huge Jacuzzi tub for two. Step out onto the balcony from the living room for a magnificent open view of the mountains. Enjoy a movie on your 65” Samsung smart H

Located in Stephentown, New York, United States. 5 Bed / 3 bath Apt Near Jiminy Peak Berkshires Welcome to the Stephentown Hotel in the heart of the Berkshire & Taconic Mountains. Completely gut remodeled, the building reopened in 2023. This is the "crown jewel" unit! 5 bedrooms / 3 bathrooms / 2 living rooms / 1 kitchen / 1 arcade. Private W/D in unit.This is for Apartment # 3. Beautiful apartment in the Stephentown Hotel, located in the only Stephentown on Earth! The building has operated almost continuously since the 1860s! The Stephentown Hotel is well known locally. The building went through a 3 year gut renovation. We are minutes away from Jiminy Peak Ski Resort, located in the world famous Berkshire & Taconic Mountains! Many fun activities nearby including Ramblewild Adventure Park, Tanglewood, New Lebanon Speedway, Cherry Plains State Park, Mount Greylock, Cinch Em Horse stables, multiple lakes, hiking trails and more! The kitchen is fully stocked with all essentials and household items. The kitchen features a large fridge, d

Located in Lanesborough, Massachusetts, United States. Mounatin Getaway in the Heart of the Berkshires! Welcome to the Lynne Court Guesthouse in the heart of the Berkshires!We are happy to share our gorgeous, nature-surrounded home with you! Your hosts are Rick and his daughter, Deena. For the most part, Deena will be the person you will interact with during your stay. Check out and check in as you please with our easy key-drop system. We offer a spacious, light-filled and attractive rental. Your stay will also be close to SO many fun activities and attractions in the beautiful Berkshires!---------------------------------------------------------------------Our big yellow house is located at the end of a cul-de-sac in a quiet Lanesborough neighborhood. Surrounded by farmer's fields and open land, our home provides stunning views of the Berkshire mountains. The best part of our rental is its LOCATION--centrally located in the beautiful Berkshires, we're close to so many options for cultural attractions and fun activities. Our large driveway