27,207 properties available

Located in New Marlborough, Massachusetts, United States. Converted Berkshire schoolhouse on a quiet river Renovated schoolhouse on a quiet river in the Berkshires. This is the perfect place to unwind. Great for families and friends to relax and reconnect. Take a walk to the waterfalls, play croquet or volleyball on the lawn, gather dinner from our seasonal garden and enjoy 'smores around the fire pit. Very private and woodsy, but close to Butternut for skiing, Great Barrington for shopping and access to all the music and art the Berkshires has to offer. We are very close to some well known restaurants like Cantina 229, Old Inn on the Green and Gedney Farm. Home is stylish, comfortable and inviting. This house is perfectly cozy and you many never want to leave it! We provide all the basic staples ranging from bandaids, shampoo and an iron to coffee, tea, oil, vinegar and some necessary baking items. You will have all the pots and anything in the fridge and cabinets. We have wifi but you can easily unplug if that's what you're looking for. S

Located in Becket, Montana, United States. Tranquil 3-BR Waterfront Retreat Summary:Retreat to the tranquility and calm of this newly-renovated lakeside chalet in the Berkshires. The home is perfectly situated for families and friends looking for a getaway; property features three bedrooms, a breakfast/work nook in the atrium, ping pong table, deck, grill, private dock, and quiant grounds alongside the lake. 5-min to Jacob's Pillow, 25-min to Tanglewood, and 30-min to skiing at Butternut. Ideal for vacations and staycations year-round.The Space:Entire 3-BR bungalow on Long Bow lake with private dock. Long Bow Lake is a small lake, great for kayaking and canoeing. Note there are no motorized boats allowed. Swimming is at your own risk / discretion.Guest Access:Accessible with a smart lockThe Neighborhood:Located in the Sherwood Greens CommunityGetting Around:Vehicle requiredOther Things to Note:Notes & Disclaimers:Wildlife: This is a home in a rural part of the country. You may see wildlife including deer, coyotes, foxes, and be

Located in Becket, Montana, United States. Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits! A beautiful retreat awaits you at this 3-bedroom, 3-bathroom vacation rental in the Berkshires! This Becket home is situated on 11 private acres of wooded land and features a peaceful pond. Venture out to explore the Berkshires, where you'll find 9 lakes, watersports, renowned spas, golf courses, skiing, dozens of hiking trails, and much more. After a day filled with art, music, and theater, enjoy world-class dining at restaurants in neighboring Lenox and Stockbridge!-- THE PROPERTY --11 Acres | Boat Dock | Hiking Trail Access On-Site Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Full Bed, Sleeper Sofa, Twin BedINDOOR LIVING: 2 Smart TVs, DVD player, wood-burning fireplace, wood-burning stove, expansive windows, natural light, dining table, ceiling fansOUTDOOR LIVING: Charcoal grill, outdoor dining, patio, screened porch, fire pit, gardenKITCHEN: Dishwasher, stove/oven, coffee maker, toaster, ice makerGENERAL: Free WiFi, line

Located in Stockbridge, Wisconsin, United States. Cozy Cabin on Lake Mahkeenac Cozy cabin located in the popular Beachwood community which is 2 miles from Tanglewood on Stockbridge Bowl, close to Kripalu, Lenox, Stockbridge, restaurants, hiking and everything else in the Berkshires. Large open yard, good size bedrooms and spacious living room area perfect for entertaining. It’s only a short five minute walk to the lake and private beach with access to swimming and an area to launch your own kayak, canoe or paddle board.

Located in Monterey, California, United States. Dock on Lake Garfield, 10 min to Butternut, Wifi, So Fun! RENOVATED Charm: 1920's cottage with 3 acres of natural surroundings. A short, 5 minute walk via nature trail and stairs to dock on Lake Garfield with Adirondack chairs, 2 kayaks and a large canoe. 5 bedrooms and 2 bathrooms provides plenty of space for your family enjoyment. At home enjoy the large, bright family room equipped with a flat screen TV with Satellite service, high speed internet & DVD player. In addition, there is a large living room and dining room area with a charming old stone fireplace. The screened in porch is another great spot to relax...featuring a table for 6 and a seating area to enjoy the (winter) views of the lake, yard & perennial garden. The kitchen has a large eating island area brightly lit with skylights and stool seating for 5. The kitchen is equipped for every cooks needs...and plenty of cutlery & plates to feed a crowd! The large master bedroom is downstairs with four additional bedrooms up

Located in Becket, Montana, United States. Little Longbow Lakefront Chalet Welcome to your Berkshire Oasis! This rustic lakefront chalet is ideally located right in the heart of the Berkshires in a private community, Sherwood Greens. Only minutes away from Jacobs Pillow, The Appalachian Trail, Otis Ridge Ski Resort, Butternut Ski Resort, and Tanglewood, there are plenty of activities all year round! You are a short drive to Lee, Lenox, Stockbridge, Pittsfield, and Great Barrington.

Located in Becket, Montana, United States. Berkshires Retreat W/ Sauna by Evergreen Home Take a break from the hustle at this unique and tranquil getaway in the Berkshires. This stylish octagonal home boasts a main house which sleeps 3-4 and a bunk house which sleeps an additional 4-5 guests. With 14 acres of beautiful private woods to explore, a red cedar barrel sauna, outdoor shower and access to center pond beach, our guests can relax, unplug and unwind. 10 minutes to Jacobs Pillow Dance, 20 minutes to amazing theater and restaurants, 30 minutes to the Berkshires best skiing.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 home is located in a rural neighborhood. You cannot see any neighbors from the house.Guests have access to entire property and grounds.Two unique spaces, a traditional one bedroom plus loft home plus a separate bunk house. The bunk house has electricity but no running water.The main floor of this home ce

Located in Stockbridge, Wisconsin, United States. Lakeshore cabin with private beach and dock A classic Berkshire cabin nestled under maple trees, on the shore of the Stockbridge Bowl cove. Serene, peaceful and private, yet close to all area attractions. Private beach and dock. Swimming and kayaking. Large lawn with lots of trees. Newly renovated. Large light-filled living room with cathedral ceiling and skylights. Main bedroom on ground floor with en suite bathroom. Two bedrooms and balcony overlooking lake upstairs. Enclosed porch and large deck with gas grill. Forest trail and waterfall next door. Easy access. Plenty of parking. 5 minutes to Tanglewood and Kripalu.Ground floor: Living room with cathedral ceilings and skylights, two sofas, chairs, electric fire and smart TV, CDs, DVDs, games, air conditioning unit, yogibo beanbag, dining room table can seat six. Bedroom with queen bed and en suite bathroom, sliding door to porch, TV monitor, work space, air conditioning unit, ceiling fan. Bathroom with shower. 2nd Bathroom with tub/

Located in Becket, Montana, United States. Berkshires Lakefront Gem. Cozy home w/ hiking, swimming & all things cultural! The perfect getaway for people who want to unwind from the grind of everyday life. Little Robin Lake is located right in the backyard! Swim, kayak or canoe directly from the private beach and dock. Hiking, dining and all the culture that the Berkshires has to offer are nearby. Tanglewood, Jacob's Pillow, Lee Premium Outlets and many unique restaurants are in close proximity. Sherwood Shoppe is a friendly country store in our neighborhood. This is a private, cozy, year-round lake house. Dine in the screened in porch or on the brick patio with full lake view, is a delight! Soak up the sunshine during the daytime, and then enjoy the night sky for stargazing. This home has an open concept living room/kitchen area with 2 sliding glass doors leading to the porch. Each room has a TV and there is fiber optic WiFi throughout the house, reaching the outside areas.There is a comfortable finished room in the lower

Located in Stockbridge, Wisconsin, United States. Centrally Located Gorgeous Cape Cod Home for Tanglewood or Shakespeare & Co Stylish Berkshires Retreat: This charming home, nestled in the heart of the Berkshires, awaits your next visit. With 5 bedrooms, dining room, 2 living rooms, 2.5 restrooms, and a screened porch, it offers both cozy comfort and spacious living. Step onto the stone patio and soak in the character of this unique property. Wake up to the soothing sounds of a nearby brook as you savor your morning coffee. Explore over 2 acres of lush land surrounding the house—a perfect setting for daily walks. Tanglewood is just a 5-minute ride away. Positioned between downtown Stockbridge and Lenox, you are close to the renowned Norman Rockwell Museum and Edith Wharton's House, near the serene Stockbridge Botanical Garden. And when the sun sets, the Stockbridge Bowl becomes your favorite summer hangout. Your daily priority list will be mostly about choosing from an array of entertainment and dining options all around you.Whether

Located in Monterey, California, United States. Monterey Home w/ Hot Tub, Pool & Game Room! Gather up your friends and family for the ultimate group getaway at this Monterey vacation rental! The home has nearly 4,500 square feet of interior space — including a game room, a huge sunroom, 6 bedrooms, 4 full baths, and 2 half baths — and plenty of outdoor space for everyone to enjoy. Plus, you’ll have easy access to endless outdoor adventures. Hit the slopes at Butternut Ski Area or Otis Ridge — both less than 10 miles away — take a hike on the local trails, or catch a show at Tanglewood!-- THE PROPERTY --MassTaxConnect ID C0463041930 | Deck w/ Gas Grill | Furnished Sunroom | 8 Mi to Butternut Ski Area | 15 Mi to TanglewoodBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed | Bedroom 5: Queen Bed | Bedroom 6: Queen Bed | Office: Queen Sleeper Sofa | Basement Bonus Room: Queen Bed, 2 Twin Sleeper Chairs | Additional Sleeping: Full Air Mattress INDOOR LIVING: 3 Smart TVs, fireplace (wood provided), pi

Located in Monterey, California, United States. Gorgeous Log Cabin in the Berkshires -- Perfect All Year Long. Stunning log cabin in The Berkshires on 10 wooded acres complete with brand new 4 season hot tub, pickleball court, fire pit, hammock, veggie garden, outdoor shower, new Weber grill, tons of indoor and outdoor games, beautiful screened in porch, stocked gourmet kitchen, radiant heated floors, family room with fireplace, finished basement with billiards, darts, big screen TV. 3 gorgeous bedrooms, 3 big bathrooms with beautiful tilework and heated floors, and even 2 extra twin beds downstairs. This is a great getaway from the hustle/bustle. Near the beach, town of Great Barrington with great stores and restaurants, Tanglewood, Stockbridge, Lenox, Butternut, theaters, and more. Relax and enjoy! It's all new, furnished and has everything you need for a perfect getaway with just family or with friends from afar.

Located in Great Barrington, Massachusetts, United States. Private Berkshires Getaway Minutes to Ski Butternut Newly renovated 4 bedroom and 2 full bath home set back from the road is a peaceful oasis. 2 minute drive to Ski Butternut, 8 minutes to downtown Great Barrington. Vaulted ceilings, heated tile bathroom floors and 2 wood burning stoves and minisplit AC/Heating systems in every room. Gas grill, covered gazebo and a firepit perfect for a year round escape. Child's play structure with two swings and a slide also on premise.

Located in Otis, Florida, United States. Farmhouse on Otis Pond A spacious farmhouse with room for 10 has a large porch with rocking chairs, access to the pond, large yard, fire pit. Quiet, peaceful, and spacious. Room for the whole family including your four legged family members

Located in Great Barrington, Massachusetts, United States. Family vacation home in Great Barrington Spacious house in excellent condition on 3 secluded acres in Great Barrington, the heart of the Southern Berkshires, available for periods from 1 to 3 weeks (1 week minimum, 3 week maximum). Rural feel, yet only 5 min from the center of town and even closer to supermarket. Skiing at Butternut within 10 minutes' drive, Tanglewood 20 minutes away. Lee outlet shopping, hiking, antique stores, etc., all within 20 min. NYC and Boston 2-1/2 hours drive. Great Barrington is a charming small town with lovely boutiques and unparalleled food stores. Winter swimming and health club at South County Community Center, a mile away.House features screened porch with teak outdoor furniture, barbecue, and deck. 4 bedrooms, 3 with queen beds, 1 with two twins. Spacious front and back yards, woods for exploring. Living room/dining area with cathedral ceiling, skylights, multi-room air conditioning, wood-burning stove. Washer/dryer, 2-car garage, fully equippe

Located in Lenox, New York, United States. Lenox, private setting, close to Tanglewood rents by month This beautifully furnished, well-located Lenox home has a brand new kitchen ! Central Air Conditioning, a King bed in both the Main bedroom and one of the guest rooms. 2 twin beds in the third bedroom. All 100% cotton linens and towels provided. The entire house and kitchen are fully outfitted with every item you could need. There is a cathedral ceiling in the large living and dining room, a great wood burning fireplace, Baby Grand Piano. The kitchen and laundry are fully equipped. The Main bedroom has French doors opening out to a large private screened porch. Hardwood floors throughout. This home is beautifully furnished and there is plenty of closet space. The 2 car garage is attached to the house and has an electric door opener for easy access in any weather. Shorter stays may be available for fall, winter and spring. Contact me ans if renting for a month. We can discuss actual dates You want. Everything is o

Located in Great Barrington, Massachusetts, United States. Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB! In 2016 Smithsonian Magazine deemed Great Barrington, "The Best Small Town in America." Manor Lane is a private French Country Estate located only 5 minutes from the heart of the Berkshires. Situated 10 minutes to both Butternut and Catamount ski mountains and 25 minutes to Tanglewood. Manor Lane is a private Estate where each room has been endowed with notable charm. A French Manor House with private pool and tennis court, formal living and dining rooms, fireplace, study and unique Gauguin Bar. The house has welcomed numerous noteworthy guests along the way including: Donovan, Roger McGuinn and Leslie Gore, jazz artists; Bobby Watson, John Hicks and Victor Lewis. Settle into the relaxing tempo of Manor Lane and let us indulge you with the kind of thoughtful extras that we take pleasure in providing.

Located in Otis, Florida, United States. Custom Home In Scenic Wooded Area near small lake, Sleeps up to 16 The House - Set privately within the heart of the Berkshires, this sky lit, bright and immaculate year round home, will bring a smile to any face! The 'great room' splashed with sunlight and a soaring 20 foot granite fireplace is the heart of this wonderful getaway. Featuring 4 king bedrooms, and a huge upstairs loft with 4 queen beds. 2 full and 1 half bath, , smart TV in sitting room with library. Direct TV and internet access, 20 x 20 patio. Outdoor entertainment includes several games to choose from: Full length Bocce court, Corn Hole Toss, Dart Board, Ring Toss, Badmitton. Let your imagination run wild, creating family fun and laughter together!After spending your day out and exploring, come back to cook away in our AWARD winning Gourmet 'Country Kitchen Magazine'. Plenty of room for all to gather while 3 or more cooks create in the kitchen. Enjoy friends and family in this open concept 16 seat dining area. Coo

Located in Austerlitz, New York, United States. Foggy Bottom Studio Foggy Bottom Studio was created for budget conscious travelers seeking a getaway without having to rent an entire vacation home. Perfect for creative people or individuals seeking escape to a secluded paradise to vacation or focus on their work. The Studio features a bedroom, living room, bathroom and kitchenette and is available weekly, Sunday through Thursday. The Studio is part of our mountain retreat, Fog Hill Cabin (located just minutes from The Berkshires, Tanglewood, Stockbridge and many popular attractions). To ensure privacy, we never rent the main Cabin and the Studio at the same time.

Located in Stockbridge, Wisconsin, United States. Two Blocks from the Red Lion Inn & next to Berkshire Theater My place is close to Stockbridge center, Berkshire Theaters, Great Barrington, Lenox, and the Berkshires in general - great views, the city center, art and culture. You’ll love my place because the view from our home looks down upon the Housatonic river, and the oldest preserve in Massachusetts - the neighborhood, the ambiance, the comfy beds, the light, the outdoors space. My place is good for couples, solo adventurers, business travelers, and families (with kids). The place is newly renovated.

Located in Becket, Montana, United States. Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards! Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. NOW WITH SUPER HIGH SPEED INTERNET (1GB service!)We are located close to Lenox, Stockbridge, Lee, Great Barrington and more.Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our local lake is a beautiful respite and available for picnicking and swimming all day long. We also have a tennis court in town that is public.A scenic drive away from the iconic Berkshires destinations including: Jacob's Pillow, Tanglewood, the Norman Rockwell Museum and historic Lenox, Stockbridge and Great Barrington where you will find dining, music, and culture. Near Williamstown where you can enjoy The Clark and Shakespeare Festivals. Fall foliage, spring in bloom, and picturesque winters are what keep us tied to the splendor of the Berkshires. Is skiing your thing

Located in Lee, New Hampshire, United States. Romantic Boutique Hotel / Bed and Breakfast - Standard King With Gas Fireplace La Chambrette is our economy oriented "Little Chamber," a room as charming as its name. Its private bath with a whirlpool tub, a small sitting area with a gas-operated fireplace, telephone, television and room-delivered breakfast provide for all your basic needs.With French-inspired design and nine exceptional rooms, this nineteenth-century parochial school turned country inn possesses a unique character that celebrates it as a truly distinctive landmark in the beautiful Berkshire Hills. Located in the heart of Lee, Massachusetts, this unique historic hostelry has delighted guests since its opening in 1990. The Inn offers spacious 500-square foot suites which include elegant canopied beds, comfortable sitting areas with warming fireplaces to end a day on the slopes, private baths with soothing whirlpool tubs, a desk, phone, and cable television. Eight-foot windows and embossed thirteen-foot ceilings, desi

Located in Austerlitz, New York, United States. Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape! Welcome to Chester! Fall head over heels in love with this gorgeous country home in the tranquil town of Austerlitz, NY. High vaulted ceilings, large view-facing windows, a fireplace, a formal dining area, and a chef-worthy kitchen are just a few of the many amenities that make this home a vacationer's paradise. Outside, you can take in the fresh air from the large patio with breathtaking views as far as the eye can see. There's plenty of comfortable seating and a dining table to accommodate dinner with your whole crew. When you're ready, head to the Berkshires for more outdoor activities, views, hikes, museums, and art exhibits than you could ever hope to see in one visit. Book now!AvantStay provides an upscale experience with services that elevate your stay and save time so you can enjoy every moment. Guests have access to a 24/7 support team. Whether it’s fridge stocking or in-home massages, AvantStay offers a

Located in Hillsdale, Georgia, United States. Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount Sunset views, huge deck, chef's kitchen, fireplace, high-speed WiFi. This home is fully-equipped for your comfort and relaxation.This home is located in one of the most beautiful areas of the Hudson Valley/Berkshires, on a quiet dead-end road, close to skiing, hiking, lakes, farms, and wineries, yet very private on the deck with endless mountain views. The house has been renovated to include an open, spacious living area and stunning new chef's kitchen with gas stove. 5 generous bedrooms, 3 full bathrooms, and 2 powder rooms make this a comfortable house for everyone to spread out.This is the perfect spot to bring together family or friends to eat on the screened porch, look at the stars from the deck at night, gather around the firepit, read by the fireplace, or watch movies in the media room on a 75" TV. Cable internet means everyone can study and work efficiently during your stay. 15 minutes to Great Ba