27,207 properties available

Located in Great Barrington, Massachusetts, United States. Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB **20% Discount for month-long stays/ 10% discount for week stays automatically applied**.*Inquire: Seasonal rental discount! **SUMMER Time is perfect to dip your toes in our local Lake Mansfield or nearby Lake Garfield*** ***Warm Right up this Winter. Featuring an OUTDOOR Hot TUB**** ***WINTER Skiing and Snowboarding- This is your spot*** 4 miles to Ski Butternut & 8 miles to Catamount Ski Mountain**Combining the beauty and solitude of our 5+ acres of wooded hills, all the while sitting conveniently just 0.7 miles from the magnificent town of Great Barrington. Sleeps 10 | Wi-fi | 2 Zone AC and Heating.---THE PROPERTY---Nestled by trees and tucked at the end of a long private driveway. Tons of yard space provide fresh views while sitting on the large front porch or sipping your favorite drink in the ultra-comfortable screened in back porch. Cap off the night sharing stories and making memories by the outdoor firepi

Located in Lee, New Hampshire, United States. Great Place - 2 BD - Kitchen - Pool  After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge We offer multiple units at this property, all of them consistently designed to give you a beautiful place to stay. While the style is consistent, the layout and view may vary by apartment.    • Apartment style accommodation with 823 square feet• Queen-size bed and pullout sleeper sofa • Fully equipped kitchen • Two full baths• TV in living room and bedroom • Accommodate up to 6 people  BEDROOM 1 - 1 Queen bed  BEDROOM 2 - 1 Queen bed  LIVING ROOM – 1 Pullout sleeper sofa   

Located in Lee, New Hampshire, United States. Modern And Spacious Berkshires Retreat 5 bdrm 3 bath This is a completely renovated 5 bedrooms and 3 baths house that is situated on a private street, 5 min drive to either Lee center or Lenox center.The main floor has an open layout that is full of light. The gourmet kitchen is fitted with top appliances and a Blue Star gas range. The main floor also has four bedrooms and two full bathrooms.The lower level has a a family room with a pool table, another bedroom, a full bathroom and the laundry/mudroom.Our house is situated on a private street where all the houses are beautifully maintained. Family friendly and incredibly quiet. The house is also very close to Lee and Lenox, 2 very quaint and charming towns that are full of nice restaurants, coffee shops, diners, antique shops, fashion boutiques and art galleries.Tanglewood, Jacob's Pillow, Shakespeare and company,Kripalu Yoga Center and Spa are all just 10 min away. During winter time, Bousquet Ski Area is just 15 min away and Ski Butt

Located in Lee, New Hampshire, United States. The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History ** Check out the Playhouse on the Netflix series The World's Most Amazing Vacation Rentals. It's included in the Gourmet Stays episode.**The Playhouse is the PERFECT venue to house friends and families of brides and grooms. Unfortunately WE CANNOT ACCOMMODATE WEDDINGS. Featured in Berkshire and Boston Magazines, #1 on VRBO in the Berkshires.Built by Westinghouse and then part of a Vanderbilt Estate, and the first property in the world to be powered by AC electricity, The Playhouse is a renovated iconic Berkshires property that once served as a theater space for America's greatest innovators, with visitors from President McKinley, to Nikola Tesla and Lord Kelvin, and is now hung with fine art, and includes an in-house yoga studio, two kitchens, seven sleeping areas and five bathrooms; amenities include lakefront access (an 8 min walk), and the best Berkshire views. Come relax at this historic home under 25' cathedr

Located in Austerlitz, New York, United States. Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires! Discover the best of the Berkshires and Hudson Valley at the Barn at Bald Mountain! Situated along the mountainous border of NY + MA; enjoy close access to Catamount and Butternut Ski Resorts, hiking trails, orchards, wineries, State Parks, 15 mins to Great Barrington, MA, 15 mins to Tanglewood, 20 mins to Bash Bish Falls, and 30 mins to Hudson, NY.This is the perfect escape to disconnect for family or friends looking to explore Upstate NY and the Berkshires and all it has to offer in every season!The spaceOur recently renovated modern styled barn is equipped with 4 bedrooms with comfortable Queen Beds w/ luxe linen bedding, 3 Baths with showers, a quaint kitchen with brand new stainless steel appliances, dining room, and two family rooms (one with a pullout couch).Plenty of space for groups up to 8 people, and your pup!Guest accessYou and your guests will have full access to The Barn at Bald Mountain sitting on R

Located in Great Barrington, Massachusetts, United States. Berkshires Tranquil Retreat With Pool Summary:Escape to your very own serene haven in Great Barrington with a private, in-ground pool on a 4-acre property. This home offers a patio, grill, and cozy fire pit, ideal for outdoor enjoyment. Inside, find a spacious kitchen with modern appliances, hardwood floors, and a living room with a Smart TV. Accommodates six guests in three bedrooms. Enjoy the convenience of having an onsite EV charger. All this, makes for a perfect spot for lasting memories in the Berkshires. Pets welcome!The Space:Welcome to your picturesque haven in Great Barrington! Outdoor enthusiasts will delight in the expansive 4-acre property, complete with a patio, in-ground pool, and fenced area for safety and privacy. Grill up a feast on the gas grill, or gather around the fire pit for cozy evenings under the stars. There is a fence that partially surrounds the house. It surrounds the pool, pool shed, and the patio. This inviting retreat offers a spacious open kitchen equi

Located in Housatonic, Massachusetts, United States. Sweet Cozy Victorian in Housatonic. Close to everything. Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.The two story duplex is airy and light. Living space downstairs has a large kitchen with a pantry, washer and dryer. Spring drinking water provided.New Dansk cookware and dinner set. Nepresso coffee machine and pods. Dining room off the kitchen seats 4 to 6 people which flows into a small lounge area. The couch pulls out incase you have guests. Upstairs is three bedrooms. One with a queen bed, one with a full bed, one with open bunks ( full on the botto

Located in Great Barrington, Massachusetts, United States. 2 bedroom Riverhouse in the Heart of the Berkshires Located between the villages of Stockbridge, Housatonic and Great Barrington. Most unique Riverhouse property located on the bank of Rising Pond of the Housatonic River.Built around 1860, the Riverhouse has been updated and outfitted for modern-day convenience but retains its charm and unique appeal. From original painted-board floors and claw-foot bathtub with shower to modern amenities this property offers spectacular views of foliage and wildlife from the deck, picture window and bathroom of this upstairs artist’s aerie, filled with original art by local artists.The only house located directly on the banks of Rising Pond of the Housatonic River, it offers spectacular views of fall foliage and wildlife and makes for an authentic Berkshires experience. Easy access from the bank of the property for small boating and sculling. Located in the heart of the Berkshires; the Appalachian Trail, Tanglewood, Shakespeare and Co., the Rockwell

Located in Lee, New Hampshire, United States. Stonebridge Cabin: Modern Amenities, Enjoy Nature! Summary:Our quiet, peaceful and nestled in the woods, is a meticulously updated modern retreat offers the quiet comfort of a home away from home. Only 5 minutes from town and in the heart of the Berkshires, this cozy cabin is a perfect escape from everyday life. Enjoy the fully appointed trappings of modernity—high-speed internet, a beautifully updated and well-stocked kitchen, hot tub, brand new stylish and comfortable furnishings, TV room, and more!Find us on social media: @stonebridgecabinThe Space:This newly renovated, beautifully designed, and tastefully decorated home can accommodate 8 guests in 4 bedrooms and 2 bathrooms.Our brand new, fully-stocked, and modern kitchen has all new stainless steel appliances, including a gas range for cooking, and a dishwasher to make cleaning up a breeze. We’ve stocked all the cooking and serving necessities, including cookware, pots, pans, plates, cups, silverware, and more. And of course, a co

Located in Chatham, New Jersey, United States. Gorgeous large renovated historic home on 10 acres with pool Built it 1850, this incredible home is one the loveliest in the area. Recently fully restored and updated, our 5 bedroom home with living room, formal dining room, den, library, and eat-in chefs kitchen is fully equipped with everything you would need to host up to 14 people, and many more on extra mattresses to be provided if needed. With 10 Acres, an enormous pool and fabulous gardens and fields, this house is set up for you and your family and friends to enjoy a country escape.

Located in Great Barrington, Massachusetts, United States. Mason's Lodge · Luxury Home - 3 Fireplaces Mins to Ski & Town Welcome to our cozy Berkshires retreat, located just a stone's throw away from downtown Great Barrington and minutes to ski slopes at Butternut! With three wood-burning fireplaces, this three-bedroom spacious and charming house is the perfect place to unwind after a day of exploring, eating, skiing, and everything else the Berkshires have to offer. We look forward to welcoming you and making your stay unforgettable!Once you step inside Mason's Lodge, you're immediately struck by the warmth and coziness of the interior. The first thing you notice is the beautiful hardwood floors and a five-flute fireplace crafted by the long-time owner and skilled mason by profession. On the first floor is a spacious living room with one of the three fireplaces that is the perfect spot for curling up with a good book or enjoying a glass of wine with family and friends. When ready, move to comfortable couches and enjoy your favorite show or mo

Located in Lee, New Hampshire, United States. Fox Hollow Luxury Ranch Laurel Lake Awesome Berkshire Location. 1000 feet of Laurel Lake frontage shared with private dock , 2 canoes and 2 kayaks. Large oversized deck with 8 person 100 jet hot tub, fire pit, grill, seating for 11. Across the street from 1500 Acre High Lawn Farm. On 220 acre Fox Hollow Estate in both Lenox and Lee. Large open concept ranch design. 5 TV's, cable, highspeed wifi. High end Kitchen-Aid appliances and amenities. Private bath in every bedroom. Parking for six vehicles, sleeps 9 - 11. Comes with lots of TLC.

Located in Egremont, Mississippi, United States. Charming historic farmhouse minutes to Great Barrington MA and Salisbury CT Update 5/31: We are new to VRBO and are thrilled with the feedback we have had from our guests thus far. You will love staying at our property if you love an old home. Please note that we offer a 10% discount for weekly rentals until our calendar books up.Experience the breathtaking views of Mt. Everett from one of the oldest homes in the Berkshires. Our meticulously maintained 1740s homestead maintains many of its original features and is a perfect place for those looking for a quiet and private place to relax and recharge.Location:Minutes to local ski areas, downtown Great Barrington, and many more attractions such as Tanglewood, Jacobs Pillow, Shakespeare and Company, Lime Rock Park, Berkshire School and more. Space:Cozy up next to one of the many fireplaces and unwind with your favorite read. Don't worry if you forgot your book, our bookshelves are stocked with a variety of interesting reads both fact and f

Located in Great Barrington, Massachusetts, United States. Historic 4-bedroom riverside home in Berkshires Summary:Elsewhere in the Berkshires was built in 1900 and thoughtfully redesigned in 2022. Tucked back from the road, the only thing you hear is the river that runs through the property. Original wood and stone work throughout, 2 fireplaces, and beautiful original touches like lead glass windows and intricate wood paneling. 5 minute drive to Butternut Skiing. 10 minute drive to Catamount Mountain Resort. And 1/2 hour drive to Bousquet Mountain ski area.The Neighborhood:The home is a quick 5-minute drive to historic downtown Great Barrington. 5-minute drive to Butternut Skiing. 10 minute drive to Catamount Mountain Resort. And 1/2 hour drive to Bousquet Mountain ski area. Norman Rockwell is from nearby (five minute drive) Stockbridge, MA and there’s a very nice Normal Rockwell museum there. Lots of farms and hiking trails around including the Appalachian trail, which is only a five minute drive. There’s great food and shopping scene in th

Located in Egremont, Mississippi, United States. Charming 7-BR 1800s Retreat 8-Min to Catamount Summary:Step into the past with this charming 7-BR 1800s retreat, just 8 minutes from Catamount. Amidst its historic charm, find modern comforts like a full kitchen, dining area, and spacious living room with a fireplace. Perfect for gatherings, it´s seven bedrooms offer ample space for family and friends. Immerse yourself in the tranquility of this historic gem and experience a blend of old-world charm and modern convenience. The residence is a 10-minute drive from Great Barrington, offering access to dining, shopping, and amenities, while Catamount is just 8 minutes away.The Space:Private 7-BR residence located 8-Min to Catamount.Guest Access:Accessible with a smart lock.The Neighborhood:Located in Egremont down the street from Prospect Lake. 3-min to French Park, 8-min to skiing at Catamount, 10-min to Great Barrington.Getting Around:Vehicle is recommended, with 4x4 or AWD in the winter. Ride shares may be unreliable.Other Things to Not

Located in Austerlitz, New York, United States. Sunny Pond by AvantStay | Secluded Estate w/ Private Pond, Gym, & Movie Theater Escape to the enchanting retreat of Sunny Pond, a charming estate nestled on a private pond among the serene forest of the Berkshires.The inside of this estate boasts multiple living areas, allowing plenty of room to spread out. The main living area welcomes you with a fireplace, and cozy ambiance, while the second living area features a casual atmosphere, making you feel right at home. These spaces invite you to kick back and spend quality time with your group. A third living area offers a more intimate setting, with a brick fireplace, rich brown interior decor, and plush leather seating.The spacious, gourmet kitchen is fit for a chef. A wrap-around island counter provides plenty of prep space, while a second island within features barstool seating for a quick snack. Fully equipped with top-of-the-line stainless steel appliances, including two dishwashers, two ovens, and two sinks, it's ready for you to co

Located in Stockbridge, Wisconsin, United States. Historic Stockbridge Villa on 25 acres sleeps 23 At the end of a tree-lined driveway, this huge private eleven bedroom villa sits by the edge of a field with garden and blackberry patch surrounded by 25 acres of woods. Walking paths reveal rocky knolls and paths circling through pine and maple trees. The private estate has ample space for a retreat, a workshop, a grand party or just family togetherness in a beautiful place, far from the madding crowd but close to highways, shopping, spas and everything you might need.Villa Favorita is ideal for a large extended family, with 6 bedrooms that can comfortably sleep couples with multiple children, and 5 bedrooms comfortable for couples or individuals.Five large rooms on the first floor are homey and rich in historic detail. The dining room with large French doors is joined to the modern kitchen through the butler’s pantry. The utility room has a new washer and dryer and a half bath. The living room with built-in bookshelves opens into a spa

Located in Great Barrington, Massachusetts, United States. The Great Escape Ski Cottage w/HOT TUB @ Great Barrington Well appointed Vacation Cottage, newly renovated by the Owners; An Architect and an Interior Designer as a Modern Farmhouse. 5 bedrooms, 4 bathrooms, 2 large living rooms, an entertaining playroom and a well-equipped Kitchen, Front and Rear covered porches w/ a Hot Tub overlooking the open forest view.The large open lawn hosts volleyball net, soccer goals, picnic tables with lighting for outdoor dining, Solo fire pit sitting area, BBQ grill and yoga matts for your early am flow.The Hot Tub for 5 is conveniently located under the covered rear porch overlooking the forest. 5 min drive from Lake Mansfield and the town of Great Barrington and other beautiful surrounding hiking trails.Complete privacy yet only about 10 min drive from 2 Ski resorts, Butternut & Catamount. 5 min drive from Lake Mansfield and the town of Great Barrington and other beautiful surrounding towns with many options for Restaurants, Shopping, Balling Ally’s,

Located in Stockbridge, Wisconsin, United States. *Labor Day Special* S Summary:"Feels good staying here! We built this house with our own hands. We chose materials and a design that we loved and we think you will too! There are ash hardwood floors, custom white pine trim and mahogany decks. The interior has an open-concept floor plan inviting abundant natural light. Guests must agree to a rental contract prior to booking."The Space:"The house is perfectly located in the center of the Berkshires. It is no more than 10 minutes from Lenox, Lee, West Stockbridge and Great Barrington. Central heating and air conditioning as well as other great features.  Guest access to near by swimming, skiing, apple picking, fall foliage views, hiking, theater, and great restaurants.  I live near by and I am happy to assist any time there are questions. My Dad is retired in the area and is also available to help.  There is a sidewalk in front of the house that goes to town. The neighborhood is great for walking, jogging, or bike riding."Guest Access:Che

Located in Hillsdale, Georgia, United States. Charming, Quiet, River Front A cozy modern log cabin nestled in the hills of the Berkshires in a large wooded area with landscaped yard and fishpond. The house was built in 2002. It is two floor log cabin with all the comforts of home. Inside is a full service kitchen and a great-room with dining and lounging spaces. You can relax and enjoy a full entertainment center with furnished recorded music and movies. Bedrooms and baths are on both the 1st and 2nd floors. There is a large wood burning fireplace with plenty of firewood. Outside you can enjoy the sounds of the Green River, which is just off the large deck that hosts a chiminea & propane firepit, to take off the chill of the evening and/or morning, and a complete charcoal BBQ including charcoal. (We also have a propaneNearby adventures: Norman Rockwell Museum, Falcon Ridge, Lenox, Bash Bish Falls, Catamount Ski Resort, Jiminey Peak, Butternut, Stockbridge, Tanglewood, Historic Egremont, Great Barrington, Lee Outlet Malls, Pittsfie

Located in Great Barrington, Massachusetts, United States. Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard Kick back among the wooded hills of the Berkshires at Half Moon. The rustic exterior of this log cabin gives way to naturally chic spaces inside. Take in the fresh air from the large deck, complete with plenty of comfortable seating, or grill out and relax in the covered outdoor dining area. Contemporary decor and a colorful kitchen create the perfect atmosphere for playful connection at home, while the charming town of Great Barrington is just a ten-minute drive away with shopping, dining, and entertainment. Surrounded by trees and tucked at the end of a long private driveway, Half Moon is a woodsy retreat packed with style, privacy, and convenience.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 variety of upgrades & experiences to enhance your

Located in Stockbridge, Wisconsin, United States. Charming home in private Beachwood Community on Lake Mahkeenac, Stockbridge This 3 bedroom, 1 bathroom home of 1000 square feet with an additional 200 square foot screened in porch with a table for outdoor dining and lounge furniture. It is located in the prized, private, lakefront community of Beachwood in Stockbridge, MA. The house is in a quiet location near the end of a dead end road and is surrounded in back and one side by woods. Fully equipped kitchen, access to private beach, a few miles from numerous cultural hotspots including Tanglewood, Shakespeare and Co., the Norman Rockwell Museum, Berkshire Theater, etc.

Located in North Egremont, Massachusetts, United States. In the beautiful Berkshires, wheelchair-accessible home-20min toTanglewood A wonderful Berkshire vacation home for the entire family to enjoy! This charming and spotless home is fully wheelchair/handicapped accessible, if needed for someone with mobility issues. It has 5 bedrooms, 3 full bathrooms and 2 half-baths. Included in all this, there is an attached one bedroom apartment, which can double as a home office. The house has a large open, fully equipped kitchen with a dining table that accommodates 10. Family and friends can relax in the huge screened-in porch room, or in the large living room with Smart TV, including Netflix and Amazon Prime. An outdoor deck off the kitchen and covered front porch are also spaces for sitting and relaxing.Master bedroom on the first floor has a king bed, and large private bath with grab bars by the toilet and in the roll-in shower. A separate bath tub is in this bathroom as well. There is also a second bedroom/office with private half bath on th

Located in Boston, Connecticut, United States. Airy Downtown 2BR w/ W/D, nr. Boston Common, by Blueground Discover the best of Boston, with this two bedroom apartment in Downtown/Financial District. with views over the city. It’ll be easy to simply show up and start living in this elegantly Blueground furnished apartment with its fully-equipped kitchen, cozy living room, and our dedicated, on-the-ground support. (ID #BOS244)Designed with you in mindThoughtfully designed with bespoke finishes, modern furnishings, and a fully-equipped kitchen, you’ll enjoy that “I’m home” feeling with this Blueground apartment. Whether you’re lounging in your stylish living room streaming the latest and greatest entertainment on the smart TV or premium wireless speaker, or getting some well-earned rest on the superior quality mattress with luxury linens, you’ll fall in love with everything this Downtown/Financial District apartment has to offer. Sleeping arrangements Queen Bed, 63in/160cm Queen Bed, 63in/160cmAmenitiesBuilding amenities uni