27,207 properties available

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

Located in Lenox, New York, United States. Lenox Chalet: Walk to Town, Mobility friendly, Amazing Views. Dog Friendly! Located in a private area of Lenox, right behind Kennedy Park, this chalet has the advantage of combining a feeling of being in the woods, with the convenience of being very close to town and all the great spots Lenox is known for. The chalet steps from Kennedy park, so hiking enthusiasts will be able to walk to an array of treks. Most of the house is laid conveniently out in the first floor, which allows for mobility, and also provides a contemporary feel. A twin, ensuite bathroom makes it convenient for families with kids. The kitchen is well appointed for all types of cooking and we encourage our guests to visit local farms to purchase produce. The house also has a cozy wood stove for winter nights and a generous deck for the summer, where guests can enjoy an amazing view of Parson's Marsh Reserve. All in, it is a magical location for a quintessential Berkshires summer experience. *Note: The property has S

Located in Lanesborough, Massachusetts, United States. Historic Stone Church in The Berkshires Hinterland Hall was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Places in 1972. Ripe with history and impeccable beauty, Ian & Jane purchased the old stone church in May of 2021, completing an extensive restoration process in accordance with the Massachusetts Historical Commission. It is with great pleasure that we open our doors to you for a wondrous stay.When entering Hinterland Hall, the ground-level sanctuary is flooded with natural light from its nine twenty-foot tracery windows, two of which feature original stained glass from 1851. The sanctuary's expansive floor plan includes its original reclaimed wide plank pine flooring with rebuilt pine pews. The thirty-seven-foot cathedral ceilings feature their original shiplap finish.Impossible to miss, the historic & rare hand-pumped organ was crafted in 1862 by the famed organ maker William Johnson of Westfield. It is number 134 of 860 ever made

Located in Lanesborough, Massachusetts, United States. Chic Berkshire Retreat by Evergreen Home Feel like you have entered your own oasis in this charming retreat. A hidden gem set far back from the road, tucked away on almost 3 acres of privacy with lush nature This 3 BR, 1.5 bath home seamlessly blends modern updates with mid-century decor, and features a brand new spacious deck to relax and take in the unobstructed mountain views. Centrally located; 6 minutes to Mt Greylock, 4 minutes to Cheshire Lake and the Ashuwillticock Rail Trail, 12 minutes to adventure at Jiminy Peak.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.This quiet rural community is a beautiful peaceful place in the heart of The Berkshires. Guests have full use of the property excluding a couple locked closets for owners storageThe interior of the home has been updated in a stylish, sleek mid century modern decor and vibe with all modern comforts and conveniences. This

Located in Pittsfield, Wisconsin, United States. Charming Apartment In Berkshire Victorian Home 3rd Floor Penthouse Unit (3 bed/ 1.5 bath). This charming apartment is located in the heart of Pittsfield's Historical District in a beautiful Victorian Home. Enjoy looking out the beautiful stained glass windows original to the home dating back to 1899 or sitting out on the front stone terrace. Whether it is lounging on the rooftop deck, catching up with friends & family in the open kitchen/dining/living area, or reading a book in the office nook; there is a little special spot for everyone's needs!The spaceThe Hollister House is located on a residential street surrounded by other beautiful Victorian homes. This unit is available for short & long-term rentals! The whole group will be comfortable in this spacious and unique space. It is within a short walking distance to the main strip, "North Street" with great shops, restaurants, and activities! Minutes from great entertainment: The Colonial Theater, Barrington Stage Co., & The Berkshire

Located in Canaan, New Hampshire, United States. Four season lake side oasis in the berkshirkes Four-season lakeside oasis nestled between the Berkshires and the Hudson River Valley and a short walk from family-friendly Queechy Lake. Near skiing, Tanglewood, Hudson and Berkshire towns. Town beach rights included.

Located in Hancock, Florida, United States. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat Summary:The most unique Suite in the Berkshires - This gorgeous Disney Themed Hotel Room will bring Mickey Magic to our 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 this suite to believe it. Fully redone for instant Magic.The Space:The Suite has a living Room, master Bedroom, Full Bathroom, and Kitchenette in 500 sq ft of Mountain Living. 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,

Located in Pittsfield, Wisconsin, United States. Berkshire Mountainside Condo Fabulous 4 season Berkshire condo rental has room for 9 guests. Ski from this condo to Bousquet Ski Area; enjoy spring rebirth and bird migration; for summer fun we are minutes to Tanglewood – summer home of the BSO, also Barrington Stage, Jacobs Pillow and world class museums are just minutes away; fall gives you the best views of fantastic foliage including a view of Mt Greylock. Ski, hike, bike and boat - you are close to it all. Let us welcome you to our 4 season vacation home. This is an uphill unit with a large deck of the living room that offers views of the Greylock mountain range and area lakes. The main level has a large great room with gas fireplace and large HD tv. The kitchen dining area is large and has seating for 8. The kitchen is fully equipped with all the necessities you would expect to find in your own home. The primary bedroom and spacious bath is on the main level with a queen canopy bed, dresser, nightstand and HD TV. A half bath is o

Located in Pittsfield, Wisconsin, United States. Beautiful Home away from Home Large comfortable spaces good for conversations, cooking together, yoga, meditation, hot tub, quiet-time and private parties.Great spaces for small pets and extra guests.We have extra bedding for drop-ins

Located in Pittsfield, Wisconsin, United States. Family-Centric Berkshire Getaway by Evergreen Home This renovated 4 BR ranch located just minutes from Lenox has everything your family needs for a relaxing getaway! Ideally located in Central Berkshire County; museums, skiing, lake life, hiking, theaters and shopping are all just a short drive away. When you're home, relax with a movie in our theater room, play corn hole in the spacious back yard, bbq on the grill, how about a game of Foosball or Pac-Man? With room for 6 adults or 8 w/kids, this lovely spot is your perfect family retreat!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.This house is ideally located in Central Berkshire County, close to many activities and features a spacious private backyard.Guests have full access to the house excluding utility room.This renovated ranch home features an open concept kitchen with stainless steel appliances fully equipped for making me