358,603 properties available

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

Located in Lanesborough, Massachusetts, United States. Wildlife Lakeside Cottage Light and bright defines the newly renovated cabin boasting spectacular wood throughout and freshly decorated rooms. Radiant heated marble tiles offer cozy warmth during cooler moments as guests gather in the large 20 x 20' kitchen. There is a downstairs queen bedroom and full bath with a Jacuzzi tub. The second floor, accessed by a fairly steep staircase, has another queen room, and a third room with two twin beds; these share a conveniently located half bath. The house has a large screened in porch and various spots both inside and out to watch the prominent wildlife. Bird lovers will be allured by an incredible sanctuary where ducks, blue herons, geese, songbirds and even an occasional bald eagle an be spotted! Outdoor activities such as running/biking, fishing/boating are an easy walk away. The abutting lake does grow weeds seasonally, especially in the summer months, which will limit water activities. For conditions during your stay message Jill.

Located in Canaan, New Hampshire, United States. Private Cottage, Come Enjoy Nature! Summary:Experience the captivating charm of a 1920 cottage. Come enjoy and indulge in the tranquility of the spacious front porch, while relishing the blissful seclusion offered by the expansive one-acre property. This location offers easy access to the Taconic Parkway, as well as close proximity to the charming Village of Chatham, Pittsfield and Albany.The Space:As you step inside, you'll be greeted by a welcoming great room adorned with cozy seating arrangements, including a leather sleeper sofa and two upholstered chairs. A tastefully placed area rug and side tables with accompanying lamps perfectly complement the warm wood floors and ceiling beams.The kitchen showcases stunning oak cabinetry that exudes beauty, complemented by modern stainless steel appliances including a dishwasher, flat top range and oven, refrigerator, and stackable washer and dryer for your convenience. Delight in the captivating scenery through the expansive picture window

Located in Hancock, Florida, United States. Mountainside Condo @ Jiminy Peak in the Berkshires Treat yourself and be our guest atour terrific mountainside getaway, a private condo nestled at the base of Jiminy Peak hidden from the ski crowds and busy parking lots! This super clean and spacious 2 bedroom, 2 full bath condo is over 1,500 sq ft and has all the necessities with plenty of extras including: new king bedroom set, stainless-steel appliances, large smart TVs, a Nintendo Switch, a washer &dryer, linens, towels, fully stocked kitchen, gas grill,2 parking spots, andfree access to Jiminy's amenities (restaurants, pools, equipment rental, gym, ski shop).It's conveniently located closeto the bunny ski lift(a 4 min walk). Skiuntil 10pm then leave the crowds behind and relax by our wood burningfireplace with Netflix, Spotify, Prime, etc. You’ll love it!In addition to the king bed and two twins, wealso provide a queen air mattress and a roll away twin bed to accommodate up to6 guests.Guests can park in the two designated spots in

Located in Lenox, New York, United States. The Penthouse, Downtown Lenox by Evergreen Home Luxury Awaits...This downtown Lenox 3 BR, 2 BA apartment just underwent a complete renovation with design, comfort, and beauty in mind. No detail has been spared from the luxurious linens (Parachute & Annie Selke) to the radiant bathroom floors. Enjoy dinner downtown, then retreat to complete serenity just steps away.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.Lenox is central to The Berkshires so anywhere you want to explore in the greater area like museums, hikes, skiing, theater are just a short drive awayGuests will be given a lockbox code to enter through the front door. Free off street parking is available.Walk up the wide stairs into your own personal high end oasis. Quarter & Rift sawn white oak floors span The Penthouse with beautiful and comfortable furniture from Design within Reach and Rove Concepts. The Chef's kitchen feat

Located in Lenox, New York, United States. Colonial House, w/Yard,7min walk to Downtown Lenox A peaceful retreat with a timeless aura, this revamped 19th-century home is brimming with old-school charm–combining colonial-style architecture with a contemporary design. Nestled on a sprawling 8712 sq. ft. lot, our 4-bed home provides ample space for all. Picture yourself on the patio, relishing open-air barbecues under the warm sunshine while your pets run freely in the backyard. Ah, yes, this could be you! And extra perks await, including lightning-fast 1 GB/s Wi-Fi and a 50" HDTV!The spaceStepping into this generous 2,089 sq. foot space, you'll be embraced by a historic elegance and retro allure that enriches your stay. Marvel at the rustic, gleaming hardwood flooring, the sophisticated collection of high-end furnishings, and the house's overall chic and vintage style aesthetic. Expect a bright and light-filled interior by day, inducing a calm and cozy vibe at night.The palpable tranquillity of our expansive estate is sure to bri

Located in Canaan, New Hampshire, United States. Hudson River Valley/Berkshires Rural Retreat Nice Cape Cod-style home located in the foothills of The Berkshires and just 11 miles northwest of Lenox and Tanglewood. The house is situated on a sunny knoll surrounded by 2.8 acres of mature woodlands that offers great privacy. The house features a modern kitchen w/ granite-counter tops, living room, dining room, two bedrooms, full bath, a screened-in, furnished 3-season porch, with TV and a day bed that converts to a twin bed on the 1st floor. The second floor offers one bedroom and a full bath with its own family room/den which includes a trundle bed that sleeps two. There is also an additional kitchen on the second floor. House is easily suitable for two-families or couples vacationing together but also offers privacy for both. The house is ideal for a romantic getaway or family gatherings and exploring the cultural riches of the Berkshires in spring, summer & fall. Come winter, the house is great for couples or families gett

Located in East Nassau, New York, United States. Escape from it all. Woods, birds, campfire and fresh air. 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 Owl's Nest & The Bear's Den. 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 Pittsfield, Wisconsin, United States. Lakeside Home With Pool-Completely Renovated On beautiful Lake Pontoosuc, this 100% renovated home is complete with a heated outdoor pool! Every detail has been attended to from stainless steel appliances, to en-suite bathrooms with king sized beds to a 70" TV in the huge family room overlooking the lake. Perfect for family gatherings, reunions, girlfriend weekends and more.

Located in Pittsfield, Wisconsin, United States. Hidden Oasis in the Mountains by Evergreen Home Escape with family & friends to this hidden oasis in the heart of the Berkshires. Enjoy the beautiful perennial gardens & sip coffee as you watch the sunrise over the mountains from the screened-in porch. Unwind in the hot tub, relax on the stone patio by the fire pit, & dine on the deck. Just minutes from Lenox & Tanglewood, this attractive 5 BR home boasts a large, fully-outfitted kitchen, comfortable Tuft & Needle mattresses, & spacious living areas with stunning mountain views.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.The property is at the top of the hill overlooking October Mountain. You will need AWD/4WD in the winter to ascend the street and driveway. The views are gorgeous and the location is just perfect. All Berkshire attractions are easy to get to from this spot.Guests will have private access to the entire home, and p