94,639 properties available

Located in Lebanon Springs, New York, United States. Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home Escape to the Berkshires and step back in time with a stay in our charming historic home, conveniently located near the Shaker Museum. Built in the late 1800s, this beautifully restored home offers modern amenities while preserving the character of its past.Enjoy the serene sounds of the waterfall from the outdoor deck or take a short walk to visit the historic Lebanon Springs. With private access to Queechy Lake, enjoy a refreshing swim or paddle in the clear waters.Take a scenic drive to Tanglewood, just minutes away, and experience the beauty of the Berkshires along the way. Explore the galleries and shops in Great Barrington, hike the nearby Appalachian Trail, or stroll through the beautiful gardens at Edith Wharton's The Mount.Whether you're planning a family vacation, a romantic getaway, or a trip with friends, our historic home offers the perfect blend of comfort, charm, and natural beauty that will

Located in Hancock, Florida, United States. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor Summary:You want to pop out of bed, walk down hall, and be right on the mountain This 1BR 1 BA Ground Floor Unit Charming Mountain 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 smart 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 new, 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

Located in Hancock, Florida, United States. Ski-in and Ski-out your front door! Wyndham Bentley Brook 2 Bd. 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

Located in Lanesborough, Massachusetts, United States. Cozy Rustic Apt in 18th c Berkshire Farmhouse This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four cute apartments. Newly updated kitchen, bathroom and furniture. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife.

Located in Pittsfield, Wisconsin, United States. Chic Pittsfield Home With A View! Summary:This true country home has a quirky layout allowing guests to gather in different areas as well as retreat to private corners. With three bedrooms, two living rooms and mountain views, this home will have a place for everyone. You’ll enjoy a gourmet kitchen, gorgeous hardwood floors throughout the home, a wood burning fireplace, and large comfortable seating. There is a large deck off of the dining area with gorgeous views of mountains. The setting is just magical!The Space:Pulling up to this home, takes you to a secluded hill surrounded by trees and picturesque views of the mountains. The main living room has comfortable seating, a crackling wood burning fireplace and large windows to help bring the beauty of the outside in. The family room boasts a large sectional sofa, a floor to ceiling brick fireplace retro-fitted with a warm pellet stove and a large Smart TV that you can log into your streaming apps such as Netflix, Hulu, amazon Prime,

Located in Williamstown, Vermont, United States. Quiet & private small horse farm only 1.5 miles to Jiminy Peak. Pet friendly. The entire second floor of our horse barn is 1000+ square feet of cozy enjoyment, featuring a queen bed in the bedroom, an open concept living room and full kitchen, a large bathroom with a washer and dryer, and a spacious entryway. A queen sleeper sofa in the living room allows for an additional two guests. Plus there is a 12’x36’ deck with a table, umbrella and four chairs, two Adirondack chairs and a gas grill.It is cozy & private, yet so close to the many area attractions such as Jiminy Peak Mountain Resort (1.5 miles), Williams College & The Clark Art Institute (both 12 miles), Mass MoCA (17 miles) and Tanglewood (21 miles). Take in the tranquility of mornings with coffee on the deck while watching the horses graze. Mid-day, grab a frozen pint glass from the freezer and enjoy your favorite beverage under the umbrella. In season, pick fresh vegetables from the back yard garden for a sunset dinner. Dur

Located in Lenox, New York, United States. 51 Church Street, Lenox MA - One Bedroom Unit Refined getawayNewly renovated downtown space fully equipped for all your needs. The kitchen has an array of cooking essentials such as pots, pans, cooking utensils, glassware, flatware and dishes. Comfortable queen bed with linens. The unit has natural light with central heat and AC providing a relaxed environment. WIFI is available through the space making for a friendly work from home environment. Refined getawayNewly renovated downtown space fully equipped for all your needs. The kitchen has an array of cooking essentials such as pots, pans, cooking utensils, glassware, flatware and dishes. Comfortable queen bed with linens. The unit has natural light with central heat and AC providing a relaxed environment. WIFI is available through the space making for a friendly work from home environment.

Located in Hancock, Florida, United States. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor Summary:Welcome to modern country comfort. This unique Suite lies right on Jiminy Peak Mountain within the Country Inn. Mountain views, upstairs by elevator near lobby, spectacular location on the mountainNo 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 redone Hotel Room will bring mountain 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

Located in Hancock, Florida, United States. SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS! This ski-in, ski-out loft is located right at the base of the mountain in the Thatcher Lodgein 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 one bedroom, one bath loft with overlooking the village and the mountain sleeps 4 and is perfect for one family, or two couples. Fully equipped kitchen has everything you need to make your stay easy.

Located in Lenox, New York, United States. 5 STAR CASUAL ELEGANCE for 5 STAR GUESTS HYDRANGEA HILL - It doesn't get much better than this for style and proximity. Hydrangea Hill (circa, 1898) is located on a quiet street less than a half-mile walking distance to downtown Lenox, and only two miles to Tanglewood's main entrance. The yard offers a garden atmosphere with a lightly wooded wetland area on the back and side. You'll recognize it immediately by the white picket fence curving around the front as the brick walkway leads you to the front door. The house features three bedrooms, each with quality linens and mattresses; one with twin beds, one with a queen bed, and a master suite with a king bed. You'll love the master bathroom, which features a Carrara marble top, double vanity, and large walk-in glass and tile shower with a spa bench. Without a doubt, the best feature in the house is the large open living space and fully equipped modern kitchen with all you need for a family gathering or for cooking an intimate gourmet

Located in Hancock, Florida, United States. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base Summary:You want to pop out of bed, walk downstairs, and be right on the mountain - this is the place for you. This 1BR, 1BA Suite features a king bed in the master bedroom that sleeps 2, plus a second fold out queen sofa bed in the living room which sleeps an additional 2. The Kitchenette comes complete with Keurig, Toaster, pots, pans, etc. 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, incl yr round heated pool etcThe Space: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, air fryers, board games, plentiful soft premium beddings, and of course one-of-a-kind t

Located in Pittsfield, Wisconsin, United States. Dancing Horse Lodge Dancing Horse Lodge is located on Horse Farm in the heart of the beautiful Berkshire Mountains with plenty of room for family and friends or just a quiet weekend retreat. Dancing Horse Lodge is a 3 bedroom, 1 bath ranch style house with a large eat in kitchen and living room. It is surrounded by many hiking trails and right next to Bosquet ski area and Berkshire West Athletic Club. It is conveniently located close to many of the best restaurants in the area and cultural venues including Tanglewood and Barrington Stage Company. The gas-wood stove in the living room is wonderful after a cool day of outdoor activity.

Located in Hancock, Florida, United States. Must See Jurassic Dino Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn Summary:Welcome to the Jurassic Era! This is the most epic suite in all of the Berkshires! Brand new, you will love all the intricate details. From the Dinosaur Containment Chamber to fossils, to of course Giant Dinosaurs, no details are left out. It is our pleasure to bring the magic of dinosaurs to your all year retreat! Note: The room is Brand New, and will be the most epic immersive Suite in the BerkshiresThe Space:But more than the most amazing suite ever that will make you an instant superstar to your little dinosaur explorer, this suite is amazing. 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

Located in Old Chatham, New York, United States. A 200 year old center hall colonial between the Berkshires and the Hudson River This property is located on an acre in a small village within easy walking distance of a gourmet country store, a tavern, and the post office. As you can see from the photos, this is a true family home with an up-to date fully equipped kitchen, a formal dining room, comfortable living room with a library of books, and many cozy spaces to enjoy.NEARBY: An easy drive to Tanglewood, Jacob’s Pillow, Hancock Shaker Village, the Norman Rockwell Museum, the Red Lion Inn, Chesterwood, historic Berkshire “cottages” such as Naumkeg and the Mount, the Berkshire Botanical Gardens, Kripalu, the Appalachian Trail, Olana, Hudson’s antique stores, the area’s fresh produce markets, and the Shaker Museum.. It’s a fun day trip to racing at Saratoga, to Mass MoCA, and to the Clark Museum.The house features a new entrance and mudroom at the rear of the driveway. Downstairs the house consists of a large living room, a formal

Located in Hancock, Florida, United States. Ski-In/Ski-Out at Jiminy Peak in the Country Inn Jiminy Peak Mountain Resort is the perfect Berkshire get away for skiing, mountain biking, snow shoeing, mountain coaster, ropes course and MORE right on property while surrounded by cultural attractions.This classic and cozy New England Ski-in/Ski-Out 1 Bedroom/ 1 Bathroom suite sleeps 4 guests with 1- king size bed, 1 - pull out sleeper sofa and a kitchenette. It is located in The Country Inn on Jiminy Peak Resort. For an easy convenient trip once you arrive you will not have get back into your car. Jiminy Peak has everything you need on property bar/restaurants, ski/ snowboard shop, general store, ski/snowboard and snowshoe equipment rentals, ski/snow lessons and school, general store and souvenir shop.The Country Inn at Jiminy Peak Mountain Resort is an all-suite hotel. Winter guests enjoy slope side access, roaring fireplaces in building lounge areas, game room witg ping pong and an outdoor heated pool, open year round. Summer gu

Located in Lenox, New York, United States. Enjoy comfortable elegance in this secluded grand home located in town Ideally located in the heart of the Berkshires on one acre of lovely private land, this five bedroom home offers a peaceful retreat. Just a few minutes walk to the Lenox town center and 2 miles to Tanglewood. This tastefully decorated home has been recently updated. Enjoy the best New England has to offer. Walk to restaurants, shops, art galleries and other local attractions. Enjoy the rich culture and history of the area. Just a 5 minute drive to enjoy Edith Wharton's The Mount, Herman Melville's Arrowhead, Miraval Spa, Blantyre, Canyon Ranch. In addition a 10 minute drive to the Red Lion Inn, Norman Rockwell Museum, Berkshire Botanical Garden, Hancock Shaker Village, and Shakespeare and Company. There is nearby Highlawn Farm where you can visit the calves and purchase local products, one of our favorites. We have theaters, wineries, breweries, pumpkin patches, apple orchards, and maple syrup farms nearby as w

Located in Hancock, Florida, United States. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous Summary:You want to pop out of bed, walk downstairs and be right on the mountain - this is the place to be. This Stylish 2BR, 1BA suite sits RIGHT on the cricket slope in the Doc Maynard Building, right across from Village Center. All the convenience without the bustle. Nothing better. It also comes with its own private parking in front with gate. This large 900 sq ft condo features brand new decor, & sleeps up to 8 with a queen, four bunk beds and a pull out sofa. You will LOVE Jiminy any season!The Neighborhood:Right on the Cricket Slope - Walk out the door and right on the mountain. No need to lug skis anywhere. Beginners will also love you are right in same building as ski school.

Located in Hancock, Florida, United States. Lovely Home for Your Berkshires Trip, Clark Museum or MASS MoCA Visit Discover the Ultimate Berkshires Retreat: The Berkshire Apple House🌟 Luxurious Comfort in the Heart of Berkshires Nestled amid the picturesque Berkshires, our cozy gem awaits discerning travelers. Explore the Berkshires by enjoying the delightful features that make our home truly exceptional. Bright and Comfortable Bedrooms: Three serene bedrooms offer restful nights and rejuvenating mornings.Separate Study Space: Ideal for remote work or quiet reading sessions.State-of-the-Art Kitchen: Equipped with brand-new, top-of-the-line appliances—a culinary haven for food enthusiasts.Inviting Living Room: Vaulted ceilings, a custom-designed library, and a decorative stone fireplace create an ambiance of warmth and elegance.Outdoor Oasis: Unwind on the lovely patio, surrounded by breathtaking mountain vistas.🌲 Explore Nearby Attractions:Jiminy Peak Resort: Just minutes away for thrilling skiing adventures.The Clark Museum: A s

Located in West Stockbridge, Massachusetts, United States. Sophisticated and secluded Lenox Mt retreat minutes from Tanglewood. New listing Escape to this chic Lenox Mountain chalet in picturesque West Stockbridge, just minutes from Tanglewood. In a secluded woodland setting on 5.5 private acres, this contemporary chalet features an open floor plan flooded with natural light, a spectacular fieldstone open fireplace, cathedral ceilings, skylights, all new stylish furniture and artwork, and a new European galley kitchen. Secluded and private, yet close to everything in the Berkshires, while incorporating queen bedrooms with luxury mattress toppers and full bathroom on each of the first and second floors, a third bedroom with two single beds, and a large open den/TV-media/game room with office and fitness equipment. Lower level bathroom with two-person, double walk in shower. Linens provided. Laundry room with washer and separate dryer. Fully glass-enclosed sunroom and spacious wooden deck with extensive seating. AC units which also heat in the w

Located in Pittsfield, Wisconsin, United States. Lake Front Home in Heart of the Berkshires Near Jiminy Peak Lakefront Home for Rent. Amazing location close to skiing, hiking, restaurants, Tanglewood and everything the Berkshires have to offer. 4 bedrooms and an additional finished sleeping area in lower level. Large open layout with two living areas overlooking the lake. Amazing master bedroom with a wall of windows and amazing views, balcony. Three decks to enjoy the views and a patio with built in firepit to enjoy in colder weather. Jiminy peak ski resort 20 minutes away, Tanglewood 20 min, Berkshire Museum 10 minutes, and of course the lake, dock, and kayaks right outside your back door.

Located in West Stockbridge, Massachusetts, United States. Modern Cabin Near Tanglewood Welcome to West Stockbridge in the Berkshires! This newly renovated modern cabin is nestled amongst the trees and located just 3 miles from the famous Tanglewood and Kripalu. Right down the street is main street where you can peruse the shops, grab a gourmet coffee, or listen to more music at the Foundry. There are restaurants, hiking trails, waterfalls and lakes less than a mile away. We are 5 minutes from the turn pike for easy directions! Come hang and enjoy all the activity and beauty.This log cabin is surrounded by tall towering trees with a quaint exterior and a surprisingly spacious open interior. Its design is updated while keeping the integrity of the cabin appeal. All bedrooms and living room have split systems with A/C and heat! The main floor includes a living room, dining room, well stocked kitchen , bathroom with shower and one king bedroom. The basement is a great kids and adult space where you can cozy up and watch movies, shoot

Located in Pittsfield, Wisconsin, United States. Beautiful Waterfront home with deep water dock on Onota Lake Our 3 bedroom, 2 bath home has a huge 3 season sun room on the second floor with an even bigger covered deck below. The main floor has the kitchen, two bedrooms, living room, the sun room and a bath. The lower floor has a huge family room with two sets of sliders onto the deck plus another bedroom and a full bath with clothes washer and dryer. The property also features a large, deep water dock for your boat. Weekly rentals are Saturday to Saturday.This house is located on beautiful Onota Lake, in the heart of the Berkshires. Great for water sports, kayaking, fishing, or just watching the sunsets. Minutes away you will also find Skiing (Bousquet, Jiminy Peak), mountain biking, hiking, live theatre (Barrington Stage, Shakespeare and Company, The Colonial Theatre), golfing (more than 5 within 15 min), water park (Bousquet), bird sanctuary (Audobon).**** Dec of 2015; We just completed several upgrades including a new gas firepla

Located in Lenox, New York, United States. NEWLY RENOVATED THREE BEDROOM HAUS IN LENOX WITH MODERN INTERIOR DESIGN. Modern, bright and renovated. Mid Century vogue furnishings, hardwood floors and central A/C are just some features you will find. Our lovely 3 Bedroom 2 full bath home is located on a quiet dead end street and a short distance into downtown. The Tanglewood Main gate is less than a mile away. Large deck with seasonal lounge and dining furniture overlooking backyard. Enjoy all that Lenox has to offer in this pristine location.Broker owned.

Located in Pittsfield, Wisconsin, United States. Spacious Historic Home in the Berkshires! Just minutes from downtown Pittsfield and surrounded by the beauty of the Berkshires is this lovely 5-bedroom, 2-bathroom vacation rental! Immerse yourself in the arts, wander around history, take a hike, or enjoy the local bites — all possible from this convenient location. After your day around town, come back to this home and sit and enjoy a show in front of the fireplace, take a soak in the soaker tub, or whip up a delicious meal in the large kitchen.-- THE PROPERTY --MassTaxConnect ID #C0404362360 | 7 Mi to Tanglewood | Grill | Covered Porch Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Full Bed | Bedroom 4: Queen Bed | Bedroom 5: Twin Bed INDOOR LIVING: Fireplace, Smart TV, dining table, ceiling fans, board games, books, laptop friendly, soaker tubKITCHEN: Refrigerator, stove/oven, microwave, dishwasher, drip coffee maker, toaster, dishware & flatware, spices, cooking basicsGENERAL: Free WiFi, washer & dryer, towels, linens, com