Vacation Rentals By Owner In Great Barrington, MA

CATAMOUNT SKI RESORT IS SEVEN MINUTES AWAY. 11 MILES TO SKI BUTTERNUT.brHIGH SPEED FIBER OPTIC INTERNET brbrOur vacation home is built into a steep, secluded, forested mountainside, near the village of South Egremont. It is a short distance from all the wonderful attractions located in Berkshire County, as well as Columbia County in New York -the heart of the Hudson Valley (only 1 mile over the mountain), and Litchfield County, Connecticut (only a 10 mile drive). There is no light pollution, and other than the sounds of nature, it is so quiet at night you can hear the beating of your heart. The house has two large decks and a smaller side deck that provide great views of the surrounding countryside. The only likely neighborhood residents you will see (we have) include bear, deer, moose, fox, eagles, hawks, ravens, and numerous owls. brTimberdoodle is close to many of the attractions for which the Berkshires of Western Massachusetts are noted for. It is five minutes away from one of the best restaurants in Berkshire County-the Old Mill. Hiking, skiing and other outdoor recreation are within 10 minutes of our vacation home, including the Appalachian and South Taconic Trails, the Jug End State Reservation, and Bash Bish Falls-the State's highest. The picturesque town and local commercial hub of Great Barrington is only a 7 mile drive. The house is only 21 miles from the famous Tanglewood Music Center, the summer home of the Boston Symphony Orchestra. Nearby cultural venues abound, including Jacob's Pillow Dance Center, Shakespeare & Company, the Mahaiwe Performing Arts Center, and the Colonial Theater.brThe kitchen, although compact, has all the appliances and equipment necessary to make fantastic meals from the locally raised and grown food that you can obtain at the many farmer's markets in the area. All essentials are included, such as towels, bed sheets, soap, toilet paper and pillows. There are fully stocked pantry shelves including coffee beans, essential kitchen staples, condiments and dry goods. The kitchen includes a Kitchen Aid ceramic top convection range, Bosch dishwasher and Fisher Paykel french door refrigerator/freezer. The kitchen inventory includes a Breville toaster, Panasonic combination microwave, steamer and convection oven, Vorwerk Thermomix (a German blender on steroids), an Instant Pot, Cuisinart food processor, Baratza Coffee Grinder, and a Technivorm drip coffee maker. The kitchen has been provisioned with fine kitchenware including from Cristel, Le Crueset, Mauviel, Finex, Wusthof and ScanPan. The upper deck contains a gas grill, and a Blaze Kamado-style charcoal grill is located in front of the house near the lower deck. For in-home entertainment, the living room has a 4K high definition television connected to a Dish satellite receiver. Both this television and the one located in the large top-floor bedroom are connected to internet streaming services provided by Roku boxes. We have no air conditioners. Because of the cool mountain air and the 1300 feet elevation, we only occasionally use the provided fans on the hottest Summer days.brTwo of the bedrooms have queen beds and the third bedroom has two twin beds.brbrA SUBSTANTIAL DISCOUNT IS AVAILABLE FOR SEASONAL RENTALS

Timberdoodle-a mountainside retreat

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$610.64

Higgins House: A 1920 Folk Victorian Retreat Close to the Town CenterbrbrWelcome to Higgins House, a beautifully restored Queen Anne Folk Victorian cottage built in 1920 and set 100 feet off the road in its own quiet, private setting. Located just a short stroll to downtown Great Barrington, Lake Mansfield, and Berkshire trailheads, this home blends historic charm with thoughtful, newly renovated comfort — the ideal retreat for families, couples, and culture-seekers alike.brbrFlooded with all-day sunlight and surrounded by mature trees, this Berkshire gem is designed for slow mornings, long dinners, and cozy evenings viewed through the lens of nature.brThe SpacebrHiggins House honors its Folk Victorian roots with original clapboard siding, cedar shakes, and a charming enclosed porch — classic New England character softened by warm, modern interiors. Inside, intentional design choices, natural materials, and curated color palettes give the home its distinctive sense of place.brFarm Kitchen & Living SpacesbrThe heart of the home is the kitchen, featuring:br • A charming breakfast nook and farm-style island. br • A gas stove with range hood, microwave, and quiet dishwasherbr • Sunlight pouring in from morning to afternoonbrbrBeyond the kitchen sits a warm, relaxed dining room and a double parlor complete with comfortable sofas and accent chairs, and a large smart TV streaming access to all popular entertainment channels. brbrMultiple seating zones allow one group to watch TV while others play games or chat in the adjacent lounge — connected but not crowded.brBedrooms (Sleeps 6 Comfortably)brHiggins House offers three spacious bedrooms, each with high-end memory foam mattresses, cotton sheets, down-alternative duvets, and four pillows per bed.brBedroom 1 – Main Suitebr • Queen bed (high-end memory foam)br • Streaming-enabled TVbrBedroom 2br • One queen bedbr • 12-inch memory foam mattressbrBedroom 3br • One queen bedbr • 12-inch memory foam mattressbrbrThe layout is ideal for families, multi-couple travel, small retreats, and visiting friends of the Berkshires.brBathroomsbrYou’ll find 2.5 bathrooms, all newly renovated:br • Full Bathroom 1: Shower with excellent water pressurebr • Full Bathroom 2: Shower/tub combo with rain shower head + handheld sprayerbr • Half Bath: Conveniently located for shared livingbrOutdoor LivingbrHiggins House is designed for following sunlight throughout the day:br • Morning: Enjoy coffee in the front porch as the sun rises over East Mountainbr • Afternoon: Move to patio to enjoy the beautifully designed goshen-stone patiobr • Evening: Consider grilling outside and enjoying the quiet hillside brUnbeatable LocationbrEverything is at your fingertips:br • 10- minute walk to restaurants, cafés, and shops of downtown Great Barringtonbr • 5 minutes to Ski Butternutbr • 15 minutes to Catamountbr • 20 minutes to Tanglewoodbr • Short drive p to Lake Mansfield — swimming, a lifeguarded beach (seasonal), picnic areas, fishing, and a flat walking trailbrAmenitiesbr • Central heatingbr • Mini splits units in every bedroom, the living room, and kitchenbr • Fast, reliable WiFibr • Laundry in basement with washer & dryer (detergent provided)br • White oak floors in living spaces; exposed wide pine floors and rugs in bedroomsbr • Parking for up to 4 carsbr • Luxury linens, towels, hairdryer, iron + ironing boardbr • Smart TV with atteamung appsbrEverything is set up to help you relax from the moment you arrive.brWhy Guests Love Higgins Housebr • A 1920s Queen Ann Victorian home with newly renovated comfortsbr • Peaceful hilltop setting with mountain and treetop viewsbr • Walkable to town, swimming, dining, and hikingbr • Perfect for families and groups seeking space, style, and serenitybr • Designed with warmth, attention to detail, and an unmistakable Berkshire spirit

3-Bedroom Victorian home within walking distance of downtown Great Barrington.

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$635.3

Summary:brbrWelcome to your home for the week in Great Barrington—a spacious, nature-surrounded retreat. Just a 2-minute drive or 15-minute walk to downtown GB. Your stay includes three bedrooms and three bathrooms, accommodating up to eight guests. Highlights include a primary suite with a jetted tub, al fresco dining on the deck, a ping pong table, and more! Experience comfort, convenience, and natural beauty in this serene getaway.brbrbrbrThe Space:brbrWelcome to your spacious retreat in the heart of Great Barrington. This comfortable home features 3 bedrooms and 3 full bathrooms, accommodating up to 8 guests. The upstairs primary suite boasts a king-sized bed, walk-in closet, and an ensuite bathroom with his-and-her sinks, a jetted tub, and a walk-in shower with a skylight. The upstairs guest room also has a king-sized bed, closet, and an ensuite bathroom with a walk-in shower featuring a skylight. The downstairs guest room includes a large closet, while additional sleeping arrangements include a trundle bed in the living room.brbrbrbrFor easy planning here are the bedroom layoutsbrbrPrimary Suite With Ensuite Bathroom: 1 King Bed (second floor) brbrBedroom 2 With Ensuite Bathroom: 1 King Bed (second floor)brbrBedroom 3: 1 Queen Bed (a third bathroom is next to it)brbrLiving Room: Trundle Bed (2 twin beds)brbrbrbrThe kitchen is fully equipped with a refrigerator, electric range, microwave, sink, dishwasher, and ample counter space. Enjoy meals at the table in the dining room set for 6, with additional seating for 2 if needed. The deck features a dining table set for 6 and a bistro table. Large windows in the kitchen offer stunning views of the surrounding nature, and a Cuisinart coffee maker is available for your convenience.brbrbrbrThe living room is a peaceful haven with a large rug, and a square-shaped coffee table. It also includes a media console with a 70 Vizio TV outfitted with Apple TV and a Sonos bar, and a welcoming fireplace. brbrbrbrThere are TVs with Apple TV in every room, offering access to streaming services like Netflix, Disney+, and ESPN+. The Sonos sound system is installed throughout the house.brbrbrbrYou can enjoy the entire outdoor space, including the deck with dining and bistro table, as well as table and bench sets near the driveway. The property is surrounded by nature, providing opportunities to spot deer, owls and a variety of other wildlife right from the house. The home is conveniently located just a 2-minute drive or a 15-minute walk from town.brbrbrbrOther things to get excited about: brbr-The driveway accommodates up to 6 cars, you'll have ample parking. brbr-For your convenience, a washer and dryer is available brbr-Two steps lead to the front door and thirteen stairs with a landing in between lead to the upstairs bedrooms. brbr-Google Nest camera located above the garage. brbr-Hot water baseboard heat and cooled with Mini Splits A/Cbrbr-Decorative fireplace! brbr-Have a fun night in with amenities such as: a ping pong table, board games and yard games.brbrbrbrBook your stay today and immerse yourself in the serene surroundings and cozy atmosphere of our Great Barrington retreat.brbrbrbrWe look forward to welcoming you soon, standard rules like no smoking, no partying, no pets and being respectful of the neighbors apply.brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrThe Neighborhood:brbrGreat Barrington, nestled in the scenic Berkshires region of Massachusetts, is a charming small town known for its vibrant arts scene and stunning natural beauty. The town offers a variety of activities for outdoor enthusiasts, including hiking at Monument Mountain, which provides trails with breathtaking views of the Housatonic River Valley, and enjoying the serene waters of Lake Mansfield, perfect for swimming, picnicking, and boating. Beartown State Forest offers additional opportunities for hiking, mountain biking, and winter sports like snowshoeing and cross-country skiing.brbrbrbrCultural attractions abound in Great Barrington, with the Mahaiwe Performing Arts Center hosting a diverse range of performances, from concerts and theater productions to classic movie screenings. The Triplex Cinema is a beloved independent theater that showcases an eclectic mix of mainstream, indie, and foreign films. For those interested in history and literature, the W.E.B. Du Bois National Historic Site honors the life and legacy of the renowned civil rights activist and scholar, who was born in Great Barrington. Fans of folk music can visit The Guthrie Center, located in the Old Trinity Church, which serves as both a venue for community events and a tribute to Arlo Guthrie.brbrbrbrThe town's downtown area, particularly Railroad Street, is lined with unique shops, boutiques, and galleries, making it a delightful spot for shopping and exploring local art. The Berkshire Co-op Market, a community-owned grocery store, emphasizes local and organic products, reflecting the town’s commitment to sustainability and supporting local farmers.brbrbrbrGreat Barrington also boasts a diverse and vibrant dining scene. The Prairie Whale is renowned for its farm-to-table menu, offering hearty, rustic dishes made with locally sourced ingredients. Baba Louie's is a local favorite for its wood-fired pizzas, crafted with organic and locally sourced toppings. Gypsy Joynt provides a quirky and eclectic atmosphere with a menu that includes sandwiches, burgers, and a variety of vegan and vegetarian options. The Marketplace Café is a casual spot for breakfast and lunch, known for its fresh, locally made sandwiches, salads, and baked goods. For a taste of Mediterranean cuisine, Aegean Breeze offers an array of Greek dishes, including seafood and grilled meats. Number Ten is a standout steakhouse known for its high-quality cuts of meat and extensive wine list, while Bizalion's Fine Food offers a deli experience with gourmet sandwiches, soups, and salads, alongside specialty groceries like cheeses and charcuterie.brbrbrbrThe town hosts several annual events that draw both locals and visitors, such as the Great Barrington Arts Walk, which showcases local artists in galleries and shops throughout downtown, and the Berkshire International Film Festival, featuring a mix of independent and international films. The Holiday Stroll in December is a festive event with caroling, shopping, and family-friendly activities, adding to the town’s charm and sense of community. With its blend of outdoor activities, cultural experiences, and culinary delights, Great Barrington is a delightful destination for both residents and visitors.brbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon, standard rules like no smoking, no partying, no pets and being respectful of the neighbors apply. The fireplace is strictly decorative. For the comfort of all guests and to help us maintain the space, pets are not allowed on the property, even for short visits.brbrbrbrPlease note that the ping pong and foosball tables are located in the unheated garage. During the winter months, the garage may be too cold for use and storage of the patio furniture, limiting its suitability for gameplay.brbrbrbrDon't worry about accidental damage! Your rental includes an accidental reported damage waiver fee of up to $800. The cost to repair any accidental and reported damage to the rented property, including any missing or broken items up to a maximum of $800, will be covered at no charge to you as long as the damage is reported to your host before you depart.

Perfect Nature Haven In Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$516.73

The Berkshires and all its attractions are at your doorstep in this newly renovated, well-insulated 1900 Victorian, situated on a quiet residential street in downtown Great Barrington. A 5-minute stroll takes you to the heart of Main Street, while short drives take to you all the area's attractions: Butternut and Catamount ski centers, Tanglewood, the Appalachian Trail, Rockwell Museum, beautiful Lake Mansfield less than a mile away, and the multitude of mountain lakes in our region. brbrThe eclectic look and feel of my home reflects my twenty years as a boutique innkeeper and restaurateur in Bali, as well as being the daughter of a New York art dealer. You'll rest well on the comfy mattresses, 100% percale cotton bedding, duvets, and both down and microfiber pillows and enjoy fine Turkish cotton towels. I've stocked the kitchen with the high-quality cookware, equipment, and utensils (think vintage All-Clad, Lodge, Cuisinart, Vitamix, Nespresso, Microplane etc) that help produce a great meal. I also have my personal spice collection that I leave for guests to use. The spacious deck behind the house has a gas grill, dining table, comfortable chairs, and sun umbrella, suitable for 6-8 people. brbrWith the house's dimmable lighting throughout as well as decorative lamps and bedside reading lamps in every bedroom, you will feel the warm ambience of every space throughout the house. brbrAnd I never like having to check out at as early as 10 am, so please settle in and sleep in. Check out time is 2 pm. brbrbrbrbr

An In-Town Beauty with Late Checkout

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$785.87

Evergreen Home Vacation Rentals invites you to this Great Barrington retreat, nestled on 4.7 park-like acres. This 3BR/3BA home is designed for wellness, featuring a private hot tub, a rejuvenating sauna, and a full gym.brbrEnjoy the convenience of a first-floor bedroom and den, plus two full baths on the main level. Located just 14 minutes from Butternut Ski Area and central to everything the Berkshires have to offer, this is the perfect base for relaxation and adventure. Book your stay!brbrIf 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.brbrbrThis private home is surrounded by beautiful hiking trails and central to many Berkshires activities.brbrGuests have access to all spaces within this home with the exception of a designated owner closet and utility room.brbrbrThis home is part of a large property, but is completely private and almost a football field away from the guest house. This is not a shared space.brbrThe open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided wood-burning fireplace, providing a cozy ambiance for your enjoyment. Delight in preparing your favorite meals at home with the convenience of our spacious kitchen island, offering ample room for culinary creativity. The open kitchen comfortably accommodates seating for four, with an additional kids' table for our younger guests to enjoy. The dining area in front of the fireplace comfortably seats 6 guests. brbrOn the ground level, you'll find one bedroom and two full bathrooms, offering both convenience and comfort. The first-floor bedroom is furnished with a Queen bed and a desk, perfect for those who need to work remotely. Both full bathrooms are conveniently located adjacent to the bedroom areas for added accessibility and ease. Additionally, there's a versatile den/office space that can easily convert into an extra bedroom with a queen-size pull-out sofa. brbrSunlight fills the hallway that connects the second floor. The second floor contains a spacious primary bedroom adorned with a Queen bed, alongside a charming second bedroom featuring two twin bunk beds. Completing this floor is a well-appointed full bathroom, offering comfort and convenience for all guests.brbrDescend into the finished basement, a haven for rejuvenation and activity. Unwind in the dry sauna, or make use of our fully-equipped gym, boasting a Peloton bike (bring your shoes!), bench, free weights, kettlebells, and all the essentials for your workout routine. Elevate your yoga practice with mats, blocks, and a full-length mirror, all while staying entertained with a motivating TV. For our younger guests, a dedicated children's play space awaits, brimming with an array of toys for endless fun and creativity.brbrStep into our serene park-like fenced backyard, where privacy and relaxation await you year-round in the inviting hot tub. Enjoy outdoor cooking with the convenience of a grill, and savor meals al fresco amidst the beauty of nature with our patio furniture and outdoor dining setup.brbrLong Pond is a reservoir in Great Barrington. It is a beautiful serene spot surrounded by nature. This is not a swimming/boating pond, but there is plenty of hiking all around the area. Pfeiffer Arboretum is just down the road which is a Land Conservancy on Long Pond featuring a .7 mile walking loop through diverse forest and wetland ecosystemsbrbrAlthough you will feel far from it all, downtown Great Barrington is just a quick 7 minute drive for shopping and restaurants! This home is only an 11 min drive to Lake Mansfield for swimming and beach access. Ski during the winter months with only a 14 minutes to Butternut Ski Area and 19 min Catamount Ski Mountain. Explore downtown Lenox and take a 20 minute drive to enjoy a show at Tanglewood.brbrHaving a car will greatly enhance your ability to explore the Berkshires effectively.brbr⭐️ LOCATION: This private home is surrounded by beautiful hiking trails and is central to many Berkshires activities, making it ideal for outdoor adventures and relaxing getaways.brbr⭐️ PETS: Small dogs may be allowed with prior owner approval. Please provide details about your pet before booking. A $100 pet fee applies if approved. No multiple pets allowed.brbr⭐️ PARKING: The property has a long circular driveway shared with the guest house, plus ample off-street parking for up to 4 cars.brbr⭐️ HOT TUB: Please keep the hot tub closed when not in use and ensure the jets are off before leaving. Guests use at their own risk and should be aware of potential health considerations.brbr⭐️ GUEST HOUSE: There is an additional guest house on the property that may or may not be occupied during your stay. The front parking circle is the only shared space. The home and backyard are fully private and fenced. The guest house cannot view the backyard.brbr⭐️ OCCUPANCY: The property can accommodate up to 8 guests. The first-floor den/office includes a pull-out queen sleeper sofa with an attached full bathroom. The sofa is a premium American Leather, more comfortable than standard pull-out couches.brbr⭐️ SECURITY: An exterior camera is located at the front door facing the driveway. There are no interior cameras.brbr⭐️ REGISTRATION: Town of Great Barrington Registration No: 003792brbr⭐️ DAMAGE PROTECTION: Your reservation includes a $20 accidental damage insurance fee, allowing you to relax and enjoy your stay with peace of mind. If any damage occurs, please notify us so we can arrange timely replacements for the next guest.

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington, Massachusetts, United States

Bed

Bath

8

Sleeps

$630.15

Summary:brbrWelcome to River Cottage, a beautifully renovated 3-bedroom, 2-bathroom riverfront gem in the heart of Great Barrington. Located along the scenic Housatonic River, this enchanting home offers the serenity of country living with the added benefit of being within walking distance to all the amenities of a vibrant, walkable community.brbrbrbrRiver Cottage is just a short stroll away from local favorites like Prairie Whale, charming shops, and the bustling Farmer's Market.brbrbrbrThe Space:brbrRiver Cottage boasts a pristine, completely renovated interior with gorgeous finishes throughout. The open-concept living and dining rooms flow effortlessly into a chef's kitchen, complete with a walk-in country pantry.brbrbrbrUpstairs, the primary bedroom features a king bed, complemented by two guest bedrooms—one with a queen bed and the other with another king bed. Two beautifully appointed bathrooms ensure privacy and convenience for all guests.brbrbrbrEnjoy your morning coffee on the charming, wrapping front porch or host a delightful al fresco dinner in the backyard’s outdoor dining area. The fenced backyard extends to the water's edge, offering stunning river views. Entertain guests on the back deck, relax in one of the many seating areas, or enjoy a cozy fire in the riverfront fire pit. brbrbrbrRiver Cottage is the epitome of a country escape, providing a perfect blend of tranquility and convenience. Whether you’re seeking a weekend getaway or a longer retreat, this idyllic home offers everything you need to relax, entertain, and enjoy the best of Great Barrington. Come experience the magic of River Cottage—where country living meets urban walkability in the most delightful way.brbrbrbrGuest Access:brbrGuests at River Cottage have access to the entire home, the front porch and yard, and backyard with patio, herb garden, fire pit, and river view.brbrbrbrThe Neighborhood:brbrRiver Cottage is located on a residential street in the heart of Great Barrington with walkable access to several grocery stores, outstanding restaurants, coffee shops, shopping, yoga, and more. You're also close to hiking, skiing, arts and cultural institutions. During warmer months the Great Barrington Farmer's Market operates every Saturday from 9am-1pm, providing the opportunity to cook family meals made with locally-sourced organic produce without getting in your car!brbrbrbrGuests at River Cottage have access to an easy walk into town via the pedestrian-only Cottage Street Bridge.brbrbrbrGetting Around:brbrRiver Cottage is approx 2.5 hours from Boston and just under 3 hours from New York City. You'll need a car to get here and get around the Berkshires, but downtown Great Barrington is just a short walk away! The house has moderate cell service, but the surrounding areas are full of cellular dead zones. We recommend downloading the region's online maps to your device prior to your arrival or any day tripping you do while you’re here.brbrbrbrOther Things to Note:brbrCooling: The home features window A/C units in both queen bedrooms, and mini-split units in the king bedroom and dining room.

River Cottage: Riverfront Home, Walkable Community

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$502.55

Summary:brbrChalet Des Collines is a gorgeous country escape set on 2 pastoral acres of a lovely meadow in the Taconic Range. Enjoy skiing or snowboarding at Catamount (a 5-min drive) or Ski Butternut (a 10-min drive), mountain biking, hiking, cultural attractions or just relaxing in the comfortable Adirondack chairs by the fire pit in the meadow.brbrbrbrThe Space:brbrThis modern 4-bedroom, 2 bathroom chalet rests on 2 private acres within the Taconic Range, offering breathtaking meadow views and mere moments from skiing and mountain biking at Catamount!brbrbrbrInside, an abundance of natural light pours through expansive windows throughout the home. The stunning great room is warmed by a large fireplace and invites you to relax on a large sectional sofa – perfect for movie nights after a day on the slopes. Prepare gourmet meals in the fully-equipped kitchen and open the sliding doors to enjoy the beautiful outdoors. Dine al fresco on the beautifully manicured gardens, taking in the fresh mountain air.brbrbrbrUnwind after a day of adventure in one of the 4 beautifully appointed bedrooms. The primary suite upstairs offers a king bed and a large picture window framing the scenic meadow views. Bedroom 2 and 3 are on the ground floor and offer a queen bed or two twin beds. Upstairs, bedroom 4 boasts another large picture window and three twin beds, ideal for kids. Two spacious bathrooms both offer tub and shower combos.brbrbrbrHead downstairs to the basement recreation room for some friendly competition around the ping pong table. brbrbrbrVenture outdoors and embrace the tranquility of your surroundings sprawling over 2 private acres. Enjoy alfresco meals or lounging on the patio, fire up the grill for an evening barbecue under the stars, or simply relax by the fire pit and soak up the breathtaking scenery. brbrbrbrWe’ve thought of everything to make your stay as comfortable and enjoyable as possible. We have heating and mini splits for year-round climate control, SONOS speakers, and a large smart TV in the great room. Fresh linens, fluffy towels, and toiletries are all provided to make packing a breeze. Plus, there's a washer and dryer available for your convenience.brbrbrbrWith its perfect blend of modern design, amenities, and stunning natural surroundings, Chalet des Collines offers the perfect escape year-round, and mere moments from skiing and mountain biking at Catamount or Ski Butternut!brbrbrbrGuest Access:brbrWe provide electronic access to the house with a personal guest code. You'll receive the code 24 hours prior to checkin, though your code will only activate at check-in.brbrbrbrThe Neighborhood:brbrThe Berkshires are a stunning mountain region and Great Barrington is at the nexus of the Berkshires and the Hudson Valley, so gourmet grocers and large supermarkets are nearby, as well as outstanding restaurants, coffee and tea shops, shopping, yoga, and more. The perfect home base for hiking and camping at Mount Washington State Forest, the Chalet is also conveniently located for skiing, arts and cultural institutions, and more. You'll find plenty of things to do!brbrbrbrGetting Around:brbrChalet des Collines is 2.5 hours from Boston and just under 3 hours from New York City. You'll need a car to get here and get around and the drive will be beautiful! Since cell service can be inconsistent in the country, we recommend that you download the region's online maps to your phone before your trip.brbrbrbrOther Things to Note:brbrA/C: The home features mini-split units throughout, with one large unit in the living room and individual units in each bedroom on both the first and second floors.

Chalet in Great Barrington near 2 Ski Areas

Great Barrington, Massachusetts, United States

Bed

Bath

8

Sleeps

$417.81

Summary:brbrModern forest hideaway in the Berkshires surrounded by trees, natural light, and quiet. Floor-to-ceiling windows, designer furniture, fireplace, and a fully equipped kitchen. Three comfortable bedrooms plus a large sectional for extra sleeping. Hiking trails nearby, Lake Garfield minutes away, and peaceful woodland views. A calm space to relax, read, cook, and reconnect with nature.brbrbrbrThe Space:brbrSlip away to a serene modern home tucked deep in the Berkshires forest, where floor-to-ceiling windows frame quiet woodlands and mornings start with birdsong. This thoughtfully curated home blends architecture, art, and nature for a calming reset. Designed and furnished by creatives, every detail is intentional, from the Dada chairs by Ferlea Italy to the Jean-Michel Frank dining table and design-forward book collection.brbrbrbrThe main level features an open living space with oak flooring, oversized windows, and a roomy sectional for movie nights or curling up with a book. A propane fireplace and Samsung smart TV logged into your favorite streaming apps, make it easy to settle in. The kitchen is equipped with high end Fisher & Paykel and Bosch appliances, a Bertazzoni range, induction cooktop, concrete tile, and a peaceful woodland view from the sink. Enjoy slow mornings with a single-cup coffee dripper and kettle.brbrbrbrThree bedrooms provide peaceful rest, each styled with warm textures and calming tones. The main-floor suite features a queen bed and its own ensuite bathroom, including a floating sink area and walk-in shower with handheld sprayer. Upstairs you’ll find a king bedroom with its own Smart TV, and a full bedroom perfect for kids or a solo sleeper. The second bath features a rain shower, handheld sprayer, and Toto washlet with heated seat. The large living room sectional can comfortably sleep two for extra flexibility. It’s a home designed for comfort and quiet, wrapped in forest stillness.brbrbrbrFor easy planning, here are the bedroom layouts:brbr • Bedroom 1: Queen Bed (main level, ensuite)brbr • Bedroom 2: King Bed (upstairs)brbr • Bedroom 3: Full Bed (upstairs)brbr • Living Room: Sectional that can sleep 2brbrbrbrOutside, you're surrounded by nature. The house feels like a modern glass terrarium in the trees, ideal for bird-watching, writing, meditating, or just breathing a little deeper. Hiking and running trails are close by, including nearby access to the Appalachian Trail. Lake Garfield is just minutes away for summer swims. A spin bike and small free-weight setup make it easy to stay active.brbrbrbrWhether you're relaxing by the fire, flipping through art books, or exploring favorites like Cantina 229, Prairie Whale, and Southfield Store, this escape gives you space to slow down, reset, and reconnect.brbrbrbrOther things to get excited about:brbr- Central Air to keep you cool all summer.brbr- Full size washer and dryer for your use.brbr- Parking on main landing space next to home can fit up to 5 cars.brbr-Approximately 3 steps to front door & main floor bedroom for those with limited mobilitybrbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon!brbrStandard rules like no smoking, no partying, and being respectful of the neighbors apply.brbrbrbrNo sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.brbrbrbrInteraction with Guests:brbrSupport team available 24 hours a day.

Light-Filled GB Oasis, Trails, Lake, Fireplace

Great Barrington, Massachusetts, United States

Bed

Bath

8

Sleeps

$635.98

A stylish 4-bedroom farmhouse thoughtfully designed with modern comfort and historic charm. Located where the Berkshires meet Hudson Valley, the house is ideal for spring and early summer escapes.brbrSurrounded by mature trees, the house offers multiple spaces to gather, with a chef’s kitchen, outdoor dining, a hot tub, and a generous yard.brbrMinutes to Great Barrington’s dining, lakes, and hiking, and about 30 minutes to Tanglewood and Hudson — an ideal year-round escape for families or friends.brbrOur home is ideal for year-round visits. In the winter, it’s perfectly situated for skiing and cozy weekends by the fire. Summer is all about the pool, gardens, and long evenings outdoors. And throughout the year, you’ll enjoy beautiful grounds and easy access to the Berkshires’ cultural attractions, hiking trails, shops, and restaurants.brbrThe Berkshires are particularly lovely in the quieter shoulder seasons. Spring brings blooming landscapes and ideal hiking weather, while fall offers spectacular foliage and crisp, scenic afternoons. It’s also a wonderful time to work remotely from the Berkshires for a week or two — enjoying great restaurants, charming shops, and local culture without the summer crowds. The pace is relaxed, the scenery is stunning, and it’s the perfect balance of productivity and escape.brbrRooms & Indoor SpacesbrbrMain-floor brbrThe main living spaces flow seamlessly into one another — kitchen, dining room, living room, and family room — creating a layout that feels both connected and comfortably distinct. Generous windows throughout invite in natural light and surrounding greenery from every angle, bringing the outdoors in while preserving a sense of privacy and retreat.brbrThe lower level also includes a full bathroom, a small guest bedroom, and a convenient kitchenette or wet bar. A semi-enclosed porch extends the living space outdoors, offering a comfortable setting for al fresco dining in warmer months.brbrLiving RoombrThis warm and inviting living room features a classic stone fireplace and generous windows that bathe the space in natural light. An oversized L-shaped sectional offers ample room to gather or stretch out in comfort — ideal after a morning hike, a ski day at Catamount, an afternoon by the pool, or simply reading fireside.brbrTV / Family RoombrAdjacent to the living room, this additional gathering space gives guests a second option for relaxing—whether it’s movie night, quieter reading time, or a kid-friendly zone including some games and toys. brbrDining Room & Chef’s KitchenbrThe open-plan chef’s kitchen and dining area are ideal for shared meals and entertaining. The layout flows seamlessly into the living areas, making social time easy. The kitchen is modern and updated while preserving historic charm. brbrUpper Floor: brbrThe upper floor is anchored by a gracious landing that connects the three primary bedrooms. Two queen bedrooms offer charming reading nooks and separate dressing areas, creating intimate spaces within each room. The primary suite features an en-suite bath and opens onto a private terrace with Adirondack chairs overlooking the lawn and mature trees — an inviting spot for morning coffee or a quiet glass of wine at dusk.brbrPrimary Suite: On the second floor, the main bedroom includes its own full bathroom (with double sinks) a reading space, a Queen bed, plus access to a private deck. brbrTwo Additional Bedrooms: Also upstairs are two further guest bedrooms, one with a Queen bed, one with two Twin beds—ideal for family or friends.brbrAn Additional Full Bathroom & Laundry Area: A second full bath and a dedicated laundry space complete the upper level to make stays easy and comfortable for groups. brbrSummary of sleeping accommodations:brbr4 bedrooms total (1 ground-floor double bed + 3 upstairs, two Queen beds, two twin beds) brbr3 full bathrooms (1 on main level + 2 upstairs) brbrAdditional living spaces (TV/Family Room) providing flexibility for various guest groups.brbrOutdoor HighlightsbrbrHeated In-Ground Pool (Seasonal)brAcross the warmer months, guests can enjoy the heated pool—perfect for relaxing post-hike, or during summer get-aways. Pool is open from Memorial Day Weekend to Labor Day, sometimes later into September if weather allows. brbrHot Tub (Year-Round)brThe large hot tub is available all year long—so whether it’s snow-covered in winter or green and blooming in summer, guests can soak under the stars or crisp air. Like most outdoor tubs, temperature can vary slightly in very cold weather.brbrGrilling Patio & Outdoor Living AreabrAround the pool/hot tub area is a well-landscaped yard with a patio and grill—ideal for al-fresco dining, lounging, and gathering. A screened porch also offers a more protected outdoor dining spot when needed. brbrLocation & GroundsbrThe house sits on approximately 2.5 acres across from Catamount Ski Area and just minutes from Great Barrington and Butternut Ski Area—making it highly convenient for winter sports, yet private and peaceful.

Heated Pool & Hot Tub • Ideal Berkshires / Hudson Valley Getaway

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$447.7

Welcome to The Docent`s House, a home with a story worth staying for. For 18 years the woman who lived here walked visitors through the galleries of the Norman Rockwell Museum telling the stories behind the paintings. It`s a home built for gathering — families and friends all under one roof. Inside you`ll find a quiet tribute to the life of a Berkshire local: an educator, community activist, and longtime Rockwell docent whose legacy this home honors. Come for the Berkshires. Stay for the story.brbrBlack History Landmarks in The Berkshiresbr➥ W.E.B. Du Bois Boyhood Homesite - 15 minutes by carbr➥ Great Barrington River Walk - 10 minutes by car. A peaceful walking trail through downtown with interpretive markers honoring Du Bois and the town`s history.br➥ Clinton AME Zion Church - 10 minutes by car. Where a young Du Bois worshipped; now home to the Clinton Church Restoration, a center for African American heritage in the Berkshires.br➥ Ashley House (Sheffield) — about 25 minutes by car. The site where Elizabeth Freeman (Mum Bett) was enslaved and from which she launched the court case that ended slavery in Massachusetts.brbr✔ High-speed Wi-Fibr✔ Fully-equipped kitchenbr✔ Indoor fireplace (gas)br✔ Air conditioningbr✔ TVbr✔ Washer br✔ Dryerbr✔ Coffee & coffeemakerbr✔ Outdoor dining areabrbrOther notable Berkshire attractions w/ drive time . . . br➥ 3 mins to Ski Butternutbr➥ 8 mins to downtown Great Barringtonbr➥ 13 mins to Lake Garfieldbr➥ 16 mins Berkshire Botanical Gardenbr➥ 17 mins to Norman Rockwell Museumbr➥ 20 mins to Catamount ski areabr➥ 22 mins to TANGLEWOOD !br➥ 24 mins to Harlem Valley rail trailbrbr✦BEDS & BATHS✦brInside we have 4 bedrooms and 2 bathrooms, all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 Queen bedbrBedroom 2 - 1 Queen bedbrBedroom 3 - 1 Queen bedbrBedroom 4 - 2 Single bedsbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a morning`s worth of coffee to get you startedbr - Learn more @ berkshire vacation rentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbrNo pets of any kind allowed at this home. Emotional support animals are not allowed. By law service animals are allowed. If you are planning on bringing a service animal please reach out to us ahead of time so we can verify paperwork. If a pet is brought on the premises without alerting us the reservation will be cancelled.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.brbrPrefer to communicate through the booking portal.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrPlease respect all quiet hoursbrPlease see the guest packet for more information.

The Docent`s House - Honoring a Legacy

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$1077.75

This charming former tavern and stage coach inn makes the perfect four season getaway. You'll feel like you've taken over your own private New England B&B. Enjoy everything the Berkshires has to offer from the shops and restaurants in Great Barrington, music and cultural events of Tanglewood to the north and great skiing at Butternut ski resort which is within walking distance of the house.brbrKnown locally as the Turning Point Inn, the main part of the house was built in 1850 and has a long history as a stage coach inn, local tavern and more recently a bed and breakfast. The layout is perfect for family gatherings when you want to be able to stay together but have your own private rooms to retreat to at night. It is conveniently located near many hiking trails (notably the Appalachian trail crosses nearby), waterfalls, swimming holes, parks, music festivals in the summer, and of course Butternut Ski resort just down the main road. Enjoy the great outdoors , downtown Great Barrington, or just a quiet night with good friends and family around the stove in a cozy dining room.brbrThis beautiful historic house features 7 fully furnished bedrooms and 6 bathrooms, 3 of which are ensuite. Each bedroom has it's own separate key and locking doors for added privacy. The main common spaces are spacious yet cozy, each possessing it's own unique charm. There is a family room with a wood burning stove and television with Chromcast and DVD player with a wide selection of DVDs. The sitting room has a working fireplace and maintains much of it's original character and decoration. The dinning room is cozy yet can comfortably accommodate 15 people with plenty of space to spare. As a former Bed and Breakfast the house is equipped with a commercial kitchen that includes a Viking stove and oven, coffee maker, toaster, water heater, microwave, dishwasher, large restaurant grade sink and professional cookware. We stock all the plates, bowls, cups and flatware you will need to entertain large groups. There is also a laundry room with a full size washer dryer.brbrDuring the summer months the main floor remains cool during the day with the stone and wood floors tempered by the cool evenings and mountain breezes. In the winter you can use the wood burning stove in the family room and the gas stove in the dining room. The fireplace in the sitting room is unfortunately under maintenance and not available for use at this time. The bedrooms on the second floor have their own air conditioners and individual smart heating controls to accommodate everyone's temperature preference. The house itself is nestled on 1 wooded acre with a large lawn. There is an outdoor picnic table where you can enjoy a glass of wine in the evening or your morning coffee. brbrPlease note that this is an old house built in the early 19th century. Things are worn and there are many imperfections. If you are looking for a brand new renovated experience, this may not be the house for you, but if you are looking for a clean large space with plenty of private bedrooms and bathrooms suitable for a large group of people and having a fun time then this is the place for you.brbrWe really fell in love with this house the moment we saw it and we know you will too. We look forward to hosting and sharing this special place with you!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$564.07

*20% month-long and 10% week-long discount automatically applied. If you don't see it applied, please feel free to reach out with questions. brbrOur home is the perfect location for your retreat to the Berkshires. Only minutes from downtown Great Barrington but you'll feel enveloped by nature in this comfortable and stylish home that sleeps up to ten guests, with no detail overlooked. brbrbrbrOriginally from 1886, but renovated as recently as 2024, this historic home with chic and thoughtful interiors has amazing nature views perfect for a country retreat in the Berkshires. This 2,400 sq foot Great Barrington home is beautiful all year around. It's located in the very best area of the fabulous Berkshires. Great Barrington is hip and charming (we have loads of recs!) and you'll feel like you're in the serene country while being less than 10 min from town. This cozy and chic home was featured in Domino Magazine!brbrbrbrNew mini-split A/C units installed in 2024 (white bedroom, green bedroom, yellow bedroom, living room, den/dining room). Kitchen and pink bedroom have powerful wall and window A/C units.brbrThe home is on 1.26 acres with protected wetlands all around and sleeps 10 people comfortably (4 queen beds + 1 king bed) and with lounging areas for hanging out including: a den with wood burning stove and piano, a dining room, a library nook, living room with a smart tv and sliding glass doors overlooking the protected wetlands. The eat-in kitchen features everything you need to cook for your crowd and seats 10 people. We stocked the kitchen with everything you need to take advantage of the BBQ, farmer's markets, specialty shops, and host a lovely dinner celebrating the bounty of the Berkshires. brbrThe home has been thoughtfully outfitted to make working remote from The Berkshires a comfortable possibility. There are three desks including a private dedicated office space. Cell service (which can be spotty elsewhere in the area) is very strong and reliable in this house and there is high speed WiFi with Google extensions for strong access throughout the home. brbrEnjoy the outdoors from the porch with a view of the back of Butternut Mountain (we're that close!) or sit in the backyard's picnic table on the gravel area and make s'mores around the fire pit. The perfect place for unbeatable star gazing on a clear night! brbrAll linens are hypoallergenic and anti-microbial. Bedroom floors are brand new cork, naturally antimicrobial and sustainably sourced. Kitchen is fully outfitted. We're happy to provide local restaurant and shopping recommendations.

Berkshires / Great Barrington Chic & Cozy, Sleeps 10

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$248.07

Five minutes from downtown Great Barrington, this apartment sits on 6 acres of open fields with a pond, running stream, and the Housatonic River all surrounded by mountains. It is only two hours from Boston, one hour from Albany and two and a half hours from New York City. This two-bedroom apartment is family friendly with many attractions nearby from nature walks to historical sites and shopping.

Apartment

Fabulous Apartment - Great Barrington

Great Barrington, Massachusetts, United States

Bed

1

Bath

Sleeps

$356.38

A perfect stay in the Berkshires!brJust 1.5 miles from downtown Great Barrington and 1 mile from Butternut Ski Area, our 1250 sq. ft accommodation provides the ideal home base for all of your Berkshires adventures. Part of the newly renovated and reimagined East Rock Inn, you'll get a dedicated parking space, mountain views and the run of the property.brOur brand-new two-bedroom unit features a gourmet kitchen with an induction stove and stainless steel appliances, including a dishwasher. The sliding glass doors lead directly to our massive backyard. brThere's a king bed in the primary bedroom, two full-sized beds in the second bedroom, and a sofa bed, so there's plenty of room for everyone. Our dining table easily seats 8 for large family and friends dinners after a day spent hiking, kayaking, exploring, or shopping in Great Barrington and beyond.brPerfect for families and groups of friends looking for their home away from home in The Berkshires.

Apartment

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Great Barrington, Massachusetts, United States

Bed

1

Bath

Sleeps

$153.13

Discover the beauty of Great Barrington from this 2-bedroom apartment. The cozy space features 2 twin beds and 1 queen bed, perfect for a small group of guests. With AC and heating, you'll stay comfortable no matter the season. Enjoy all that Great Barrington has to offer when you stay at our place.brEverything is new in this apartment. New beds, new appliances, freshly painted walls and ceilings. This apartment is in a rural area but only 2.5 miles to the downtown. Nature abounds here with plenty of native flora and fauna observable from the private back patio.

Apartment

Charming 2-bedroom apartment in Great Barrington, set in nature.

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$602.51

Welcome to your perfect getaway in the Berkshires! Nestled beside Jug End Reservation and the Appalachian Trail, this modern home boasts valley views and a cozy fireplace in the main living area. After a day of outdoor adventure, relax on the screened-in porch or enjoy the outdoor dining area, complete with a grill for meals outside with family and friends. Experience the unique charm of this one-of-a-kind retreat—your special escape awaits! Book now for an unforgettable experience!brbr✔ Picturesque backyard and valleybr✔ High-speed Wi-Fibr✔ TVbr✔ Firepitbr✔ Washer & dryerbr✔ Free parkingbr✔ Gourmet kitchenbr✔ Cozy fireplacebr✔ Pet-friendlybr✔ Pack n Play Travel Crib (Upon request)brbr ➥ 1 min to Jug End Reservebr➥ 5 mins to Catamount Ski Areabr➥ 6 mins to W.E.B. Du Bois National Historic Sitebr➥ 9 mins to Harlem Valley Rail Trailbr➥ 12 mins to The Mahaiwebr➥ 13 miins to Bish Bash Fallsbr➥ 17 mins to Ski Butternutbr➥ 19 mins to Bartholomew`s Cobble Reservationbr➥ 21 mins to Beartown State Forestbrbr✦BEDS & BATHS✦brInside we have 3 bedrooms and 2 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 King bedbrBedroom 2 - 1 Queen bedbrBedroom 3 - 1 Twin bunk bedbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbr• DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.brbrThere is space for parking multiple cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

Jug End Crest | Fireplace • Sunroom • Central Air

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$800.86

Charming four bedroom house on the hill with convenient access to downtown Great Barrington. Just a few blocks to the beach at Lake Mansfield!brbrA ten minute walk puts you right into the middle of downtown Great Barrington, full of coffee shops, boutique shops, and charming little restaurants. brbrIf town isn`t your thing, swing by one of the organic grocery stores and cook you and your guests a meal to enjoy on the back patio.brbrPerfect getaway for families escaping for the weekend!brbr✔ Garagebr✔ High-speed Wi-Fibr✔ Smart TVbr✔ Full kitchenbr✔ Washer & dryerbr✔ Free parkingbr✔ Heatingbr✔ Outdoor dining areabr✔ Gas Grill & Outdoor fireplacebr✔ Pack n Play Travel Crib (Upon request)brbr➥ 5 mins to The Mahaiwebr➥ 6 mins to W.E.B. Du Bois National Historic Sitebr➥ 10 mins to Ski Butternutbr➥ 14 mins to Beartown State Forestbr➥ 15 mins to Catamount Ski Areabr➥ 17 mins to Norman Rockwell Museumbr➥ 19 mins to Harlem Valley rail trailbr➥ 22 mins to Lake Garfieldbr➥ 25 mins to Bish Bash Fallsbrbr✦BEDS & BATHS✦brInside we have 4 bedrooms and 2.5 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 King bedbrBedroom 2 - 1 Queen bedbrBedroom 3 - 1 Queen bedbrBedroom 4 - 1 Full bedbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbrNo pets of any kind allowed at this home. Emotional support animals are not allowed. By law service animals are allowed. If you are planning on bringing a service animal please reach out to us ahead of time so we can verify paperwork. If a pet is brought on the premises without alerting us the reservation will be cancelled.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.brbrOne parking space in the garage available for guests. Additional parking in driveway.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

Pothul Perch | Walk to Lake • sleeps 8

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$1109.18

Nestled in the foothills of East Mountain, just minutes from the center of Great Barrington, this woodsy summer chalet has been completely reimagined with featuring stunning 30-foot ceilings with skylights, an open floor plan, a wood-burning fireplace, a chef's kitchen with an automated downdraft venting system, new patios, decks, balconies, a refinished seasonal swimming pool, gas & charcoal grills, private hiking trails abetting the State Forest, and an abundance of unique outdoor areas to enjoy summer in the Berkshires. brbrEach bedroom is equipped with an individual climate control unit. The Primary Suite features a private balcony overlooking the pool, a large walk-in shower and a separate soaking tub with jacuzzi jets. The East bedroom often doubles as an office, equipped with a desk and a printer. It also boasts of an enormous private patio to watch the stars or do yoga surrounded by trees. The Middle bedroom is perfect for kids or an adult couple and has its own closet space. The West bedroom features a small porch with direct access to the yard and two twin-sized beds. The living room features a 70 SmartTV w/ a bluetooth enabled soundbar, to stream all of your favorite music, podcasts, shows, movies and live events.brbr***PLEASE NOTE*** There is a bridge closure that does add time coming in and out of Great Barrington town center. brbr*** ALSO *** We recently added blinds/shades and curtains to all of the windows in the upstairs bedrooms (not pictured in the photos)

Summer Chalet w/ Pool, Firepit + Private Hiking Trails in Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$411.06

Art and history meet breezy mountain adventures at this Great Barrington vacation rental! This 4-bedroom, 2-bathroom house boasts a private setting, the comforts of home, and an ideal location 1.3 miles from Butternut Basin Ski Lodge. See the sights at the Norman Rockwell Museum, attend a summer concert at Tanglewood, or stop by the Naumkeag, a 48-acre masterpiece known for its elegant public gardens and historic home - all within 15 miles so you can make the most of your stay in the Berkshires.brbr-- THE PROPERTY --brbr1,650 Sq Ft | Dutch Colonial | Completely Remodeled | Outdoor Gazebo w/ Gas Grill (seasonal)brbrModern updates and comfortable accommodations make this exquisitely located home the ideal spot for your weekend getaway with friends!brbrMain Bedroom: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Beds | Living Room: Full Rollaway BedbrbrINDOOR LIVING: 40-inch wall-mounted & gaming quality Smart TVs (in each bedroom), 65-inch living room Smart TV, open layout, hardwood floorsbrKITCHEN: Fully equipped, stainless steel appliances, Keurig drip coffee maker, toaster oven, cooking basics, dining table & chairsbrGENERAL: Free high-speed WiFi (400 Mbps), washer/dryer, linens & towels, electric baseboard heaters, electric blow dryer in each bathroom, electric split mini heaters for each room (heat & A/C)brFAQ: Stairs to access, all bedrooms on 2nd floor, complimentary starter set (bottled water, coffee, tea, & laundry detergent), 4 exterior security cameras (facing out)brPARKING: Driveway (4 vehicles)brbr-- THE LOCATION --brbrSKIING: Butternut Ski Area (1.3 miles), Catamount Mountain Resort (13.7 miles), Bousquet Ski Area (18.9 miles), Jiminy Peak Mountain Resort (35.7 miles)brOUTDOOR ADVENTURE: East Mountain State Forest (0.9 miles), Monument Mountain (6.0 miles)brARTS & HISTORY: Naumkeag (9.4 miles), Norman Rockwell Museum (9.8 miles), Berkshire Botanical Garden (10.2 miles), Tanglewood (13.2 miles), Berkshire Museum (21.2 miles), Hancock Shaker Village (21.5 miles)brLOCAL EATS: Xicohtencatl Restaurant (3.4 miles), Aegean Breeze Restaurant (4.0 miles), Baba Louie's Sourdough Pizza (4.4 miles), The Bistro Box (6.0 miles)brAIRPORTS: Bradley International Airport (45.1 miles), Albany International Airport (57.9 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs and may be difficult for guests with limited mobility br- NOTE: All bedrooms are located on the 2nd floor br- NOTE: The property sleeps 8 guests in the 4 beds, but the maximum occupancy is flexible up to 9 with the use of the full rollaway bedbr- NOTE: Your safety matters. This property features 4 exterior security cameras. Camera 1 is located by the front door facing the front outdoor entry, camera 2 is on the garage facing the driveway, camera 3 is on the side of the house facing the driveway, and camera 4 is on the back of the house facing the back sliding glass door entry. All cameras are outward facing and do not look into any interior spaces. The cameras record video when activated by motion. They will record when they first sense motion and 30 seconds after the last motion is detectedbr- Masstaxconnect # 1-000-963-648br- MassConnect Room Occupancy Certificate #: C0298621130

Cozy Great Barrington Home ~ 1 Mi to Ski Resort!

Great Barrington, Massachusetts, United States

Bed