New Marlborough, MA Vacation Rentals

Meadow Top Cottage is charming and cozy 3-bed, 2-bath cottage in the quiet hamlet of Mill River, MA. The 72-acre property offers exquisite views of the Litchfield hills, an outdoor patio and a fire pit nestled in a pine grove. The town’s charms include: candlelit dinners at The Old Inn on the Green, provisions at the Mill River General Store, brunch at the Southfield Store, swimming at Umpachene Falls, and hikes both on and off the property. Winter skiers are also within 15-20 minutes of Butternut and Catamount. With natural wood finishes throughout, Meadow Top Cottage exudes a quaint and homely charm that makes it a true countryside haven. The cozy living room, complete with a brick fireplace and TV, is perfect for relaxing evenings. The fully equipped kitchen, featuring flatware, silverware, cookware, and appliances, caters to both seasoned chefs and casual cooks alike. The cottage features three inviting bedrooms (1 Queen, 1 Full, and 2 Twins), ensuring a restful night’s sleep for all guests. Two well-appointed bathrooms provide modern convenience and comfort. Step outside to discover the true essence of country living. Wander through the mature gardens before settling on the outdoor patio. This space is perfect for alfresco dining or simply relaxing while soaking in the serene landscape. Enjoy a barbecue on the grill or gather around the pine grove fire pit for cozy evenings under the stars. We strive to make your stay as easy and enjoyable as possible by providing fresh linens, fluffy towels, and toiletries. The kitchen is equipped with basic essentials including a coffee maker and grinder, a full set of pots and pans, plates, and cutlery. Stay connected with WiFi by Spectrum and stream your favorite media on the Smart TV. Escape the hustle and bustle of everyday life and immerse yourself in the tranquility of Meadow Top Cottage. Whether you’re looking to relax, explore, or create unforgettable memories with loved ones, this charming country retreat is the perfect destination. Book your stay today and experience the magic of Meadow Top Cottage. Guests have exclusive access to the cottage and a private outdoor space with grill, table and chairs; access to the larger 56-acre estate is shared, which includes lush grounds and a rolling landscape. The pool and hot tub on property are not included in the cottage amenities. Meadow Top Cottage is under 3 hours from Boston and 3 hours from NYC. You’ll need a car to get here and to get around. The house has an internet connection and moderate cell service with AT&T, T-Mobile and Verizon. The Berkshires is full of cellular dead zones, so we recommend downloading the region’s online maps to your device prior to arrival or any day while you’re here at the cottage. The cottage has a shared driveway, so please make sure you do not park in the circle of the driveway. Either pull into one of the spots or use the garage. Thank you! A/C: The house has 2 window AC units for cooling and does not have central AC. License number: C0496912030

Welcome to Steepletop Lodge, a beautiful 4 bed/ 2 bath modern retreat with endless opportunities to unplug and forest bathe. A wall of windows overlooks serene woods and wetlands, and the screened porch welcomes a full three seasons of respite, situated to catch Summer breezes; with a fireplace to keep cozy in the Fall. Modern, bright, well-appointed, and stocked with games, Steepletop Lodge is a special place to reconnect with both nature and your loved ones! Following the stone path up to the front door, a spacious foyer welcomes you and seamlessly connects to the open-concept living area, with tall ceilings and flooded with natural light from a wall of windows showcasing the property’s wooded views. The living room features a woodburning stove and comfy seating, creating a cozy atmosphere within the open layout. Adjacent to the living room, find an enclosed porch with a fireplace, dining table and lounge area, perfect for enjoying nature in any weather. The kitchen is efficiently laid out and fully equipped, with an island and breakfast bar for easy meal prep and casual dining. A repurposed bowling lane serves as the dining table, inviting guests to gather for memorable meals. Three bedrooms and two baths occupy one side of the main floor. The primary bedroom offers a queen bed, a reading nook, and an ensuite bath with a walk-in shower. Large glass doors open directly onto your private deck. A second bedroom with a full bed and a twin trundle includes a convenient desk area. A full bathroom serves the bedrooms, featuring a bathtub/shower combo. A third bedroom, with twin beds, boasts a cozy reading area and charming decor. Downstairs, enjoy recreational and fitness options including a stationary bike, treadmill, ping pong table, and cozy seating area with a TV for relaxation. A fourth bedroom offers a queen bed with and convenient work space for remote work. Lastly, a laundry room completes the lower level of the home. Steepletop Lodge has been a beloved family gathering place for years, offering the perfect setting to create lasting memories with loved ones. There is a lockbox and a key inside the screened in porch. We will provide you the code during your check in process. Steepletop Lodge is approx. 2.5 hours from Boston and 3 hours from New York City. To enjoy the expansive beauty of the region, you’ll need a car to get here and get around--and the drive will be stunning! 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. We strongly advise using or renting a car that has all wheel or 4 wheel drive to access the property, especially in the colder months. *NOTE: The house does not have air conditioning; however, ceiling fans are installed in each bedroom, and additional portable fans are available throughout the home. *Please also note that two of the three first-floor bedrooms have curtains, while the third first-floor bedroom and the fourth (basement) bedroom do not have window coverings. License number: 1-454-619-424

Welcome to Forget-Me-Not by AvantStay! Bold, modern design perched right above the shores of Lake Garfield. Forget-Me-Not is a vast, three-story Berkshires retreat with unobstructed lake views, a lofted, industrial-chic design, and plenty of ways to keep your group comfortable and entertained. The home’s moody exterior gives way to a bright, open common area where you’ll find huge windows for tons of natural light, a spacious kitchen, and vaulted ceilings over the main living room. A cozy sunroom leads to Forget-Me-Not’s large deck, which features a BBQ grill and outdoor dining table for al fresco meals overlooking the water. Soak in the hot tub, or head inside for a round of ping pong, cornhole, or heat up in the custom-built sauna. The lower floor features a second living room complete with a kitchenette and pool table, so your group will have plenty of room to spread out. With tons of privacy and unbeatable proximity to the shoreline, this contemporary lake retreat is ready to show you the best of the Berkshires. AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips! A visit to the Berkshires in western Massachusetts is a treat for anyone looking to pair stunning rural landscapes with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods provide a wide range of outdoor activities, from rafting and fishing in the summer to skiing and tubing in the winter. Stunning at any season, this New England region is also famous for its farm-to-table food scene and local breweries. Come see for yourself! Local Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort *Home Truths:* - The dock is seasonal, it must come out of the water in fall & winter, like most docks on the lake, because the ice may permanently damage the docks. - We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay’s approval there is a fine of $500 per pet. - The driveway is paved and steep, making it suitable only for 4WD/AWD vehicles, particularly in winter months. - Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request. - This home is located in the Berkshires, so you may encounter wildlife such as bugs and insects. - Guests must be 25 years or older to book this home. ​​​​​​​Parking Details: Driveway space for 2 cars to park, and parking on the other side of the road, ~6 spots total ​​​​​​​ This home comes with a pack n’ play travel crib available. A high chair can be provided upon request with at least 24hrs advanced notice. Just ask and we are happy to accommodate you and your little ones! --- The room configuration is as follows: Primary Bedroom / King bed Bedroom 2 / 2x bunk beds Bedroom 3 / King bed Bedroom 4 / King bed + 2 twin size tri-fold sleeping mats --- This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We’ve enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards. IDs will be requested for verification after booking. All bookings over 30 days require a security deposit. We report and prosecute all Credit Card Fraud. ​​​​​​​Tax #C1148950976 Licence number: C0399281930

Get carried away to this quaint 3-bedroom, 1-bath vacation rental in beautiful Monterey, Massachusetts. Surrounded by scenic landscapes, this cozy cottage is the perfect place to rest and recharge. Spend your days enjoying water sports from the private dock, hiking the Appalachian Trail, or taking a scenic drive to the town of Great Barrington. In the evenings, relax on the deck and fire up a feast. Immerse yourself in the natural beauty and serenity of the Berkshires at this delightful home! -- THE PROPERTY -- MassTaxConnect ID C0467761930 | Walk to Private Boat Dock | Free WiFi | Washer & Dryer | Near Outdoor Recreation Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Full Bed | Additional Sleeping: Pack ‘n Play OUTDOOR LIVING: Spacious deck, screened-in porch, gas grill, dining area, 2 kayaks, beach towels, fire pit (wood not provided) INDOOR LIVING: Open layout, Smart TVs, breakfast bar, fireplace (decorative) KITCHEN: Refrigerator, microwave, stove/oven, dishwasher, cooking basics, dishware/flatware, coffee maker, trash bags/paper towels, toaster oven, Crockpot GENERAL: Linens/towels, split A/C unit (living room), complimentary toiletries, hair dryer FAQ: Single story, steps required to access PARKING: Driveway (2 vehicles) -- THE LOCATION -- SUN & SAND: Lake Garfield Boat Dock (0.2 miles), Lake Garfield Beach (2 miles), Otis Town Beach (9 miles), Lenox Town Beach (13 miles), Sandy Beach at Laurel Lake (13 miles) WILD & FREE: Bidwell House Trails (3 miles), Diane's Trail Trailhead (4 miles), Beartown State Forest (6 miles), Tolland State Forest (13 miles), Monument Mountain Reservation Parking (14 miles), Otis State Forest (14 miles), Granville State Forest (18 miles) MONTEREY MUST-SEES: Bidwell House Museum (3 miles), Norman Rockwell Museum (16 miles) REEL IT IN: Berkshire Rivers Fly Fishing (12 miles), Trout Pond View (13 miles), Berkshire Bass Tackle Store (15 miles) AIRPORT: Bradley International Airport (39 miles) -- REST EASY WITH US -- Evolve 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. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story property requires steps to access - NOTE: The fireplace and hot tub are unavailable for guest use Licence number: C0467761930

Welcome to Copper Kettle Farm by AvantStay, a newly renovated farmhouse retreat set across 52 sweeping acres in southern Berkshire County. Designed for restorative escapes and joyful gatherings, this charming home blends Colonial-era character with fresh, modern comforts—creating a space that feels both timeless and thoughtfully updated. Inside, the farmhouse opens into bright, inviting living spaces made for connection. A brand-new kitchen anchors the home, fully stocked and outfitted with new appliances, perfect for shared meals and lingering conversations. Multiple gathering areas allow groups to spread out with ease, including a quiet play space for children and a cozy living room with a sofa and doors that fully close—ideal as an additional private sleeping or lounging area. Throughout the home, new beds, bedding, and updated bathrooms ensure comfort at every turn, while zoned heating and air conditioning, WiFi, Roku TV access, and a new washer and dryer add everyday convenience. With four spacious bedrooms and 2.5 bathrooms, Copper Kettle Farm is designed to welcome families and larger groups alike, offering both togetherness and room to unwind. Step outside, and the landscape truly steals the show. Rolling farmland stretches toward the Appalachian Mountains, creating a serene backdrop for morning coffee or golden-hour gatherings. Adirondack chairs, a grill, a fire pit, and an outdoor dining set invite you to linger outdoors, soaking in the views and the quiet rhythm of the countryside. The property also offers direct access to highly rated hiking trails and cycling routes, making it easy to explore the surrounding natural beauty right from your doorstep. Perfectly positioned, the farm serves as a central home base for discovering the best of the Berkshires and nearby northwest Connecticut. Spend your days exploring the charm of Great Barrington, Stockbridge, Lenox, and Lee, or venture to Salisbury, Lakeville, Cornwall, and Kent just over the state line. The home is especially well-suited for visits to local private schools—including Berkshire, Hotchkiss, and Salisbury, all within 20 minutes—and for winter escapes to Catamount and Butternut ski areas. Whether you’re gathering with family, reconnecting with friends, or simply seeking a peaceful countryside reset, Copper Kettle Farm offers space, scenery, and comfort in equal measure—an unforgettable setting for making memories that last. AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips. A visit to the Berkshires in western Massachusetts is a treat for anyone looking to pair stunning rural landscapes with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods provides a wide range of outdoor activities, from rafting and fishing in the summer to skiing and tubing in the winter. Stunning at any season, this New England region is also famous for its farm-to-table food scene and local breweries. Come see for yourself! Local Attractions: Beartown State Forest, East Mountain State Forest, Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort Home Truths: - Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay’s approval, there is a fine of $500 per pet. - Please note that the fireplaces are non-operational and are for decorative purposes only. - A property manager lives in a separate building sharing this home’s driveway. Parking Details: - Parking is available for 8 vehicles. This home comes with a pack n’ play travel crib and a high chair available. --- The room configuration is as follows: Primary Bedroom / King bed Bedroom 2 / Queen bed Bedroom 3 / Queen bed Bedroom 4 / 2 full-over-full bunk beds, 1 XL twin over XL twin bunk bed --- This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. We report and prosecute all Credit Card Fraud. Licence number: C0549192670

2,262 Sq Ft | Ping-Pong Table | Nestled on Mill Pond | < 6 Mi to Dwtn Great Barrington Take a break from the city and book this Sheffield vacation rental in the Berkshires! The 3-bed, 2-bath house boasts a retro interior, a full kitchen, a wood-burning fireplace, and stellar pond and fall color views! Conveniently located near Catamount Mountain Resort, Butternut Ski Area, the Appalachian Trail, and more, this home is the perfect choice for those seeking both adventures and relaxation! -- THE PROPERTY -- C0383872670 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 full bed - Bedroom 3: Twin Bunk Bed INDOOR LIVING - Smart TV w/ cable, dining table - Wood-burning fireplace - Board games, books - Dining table, ping-pong table - En-suite bathroom, natural light OUTDOOR LIVING - Waterfront, Solo Stove Yukon fire pit - Private yard, enclosed porch - Small covered deck, dining set KITCHEN - Refrigerator, stove/oven, dishwasher - Dishware/flatware, cooking basics, spices - Drip coffee maker, microwave, toaster GENERAL - Free WiFi - Central heating, window A/C units, ceiling fans - Linens/towels, washer/dryer - Complimentary toiletries, hair dryer FAQ - Exterior security camera (facing out) ACCESSIBILITY - Single-story home, 2 steps to enter PARKING - Garage (2 vehicles) - Driveway (2 vehicles) -- THE LOCATION -- - Near waterfalls, hiking & skiing - 4 miles to Appalachian Trail - 7 miles to Catamount Mountain Resort - 9 miles to Mill River Historic District - 10 miles to Butternut Ski Area and Tubing Center - 49 miles to Bradley International Airport -- REST EASY WITH US -- Evolve 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. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - Your safety matters. This property features 1 exterior security camera located on the garage, facing outward toward the driveway. It does not look into any interior spaces. The camera records video and sound when activated by motion. It will record when it first senses motion and 30 seconds after the last motion is detected - This single-story home requires 2 steps to enter

Welcome 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. River Cottage is just a short stroll away from local favorites like Prairie Whale, charming shops, and the bustling Farmer’s Market. River 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. Upstairs, 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. Enjoy 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. River 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. Guests 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. River 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. Cooling: The home features window A/C units in both queen bedrooms, and mini-split units in the king bedroom and dining room. License number: 1-286-847-264

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 Tanglewood Bedroom 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), ping-pong/pool table, arcade machine, foosball table, board games, home office OUTDOOR LIVING: Pool (depth 4’-9’), hot tub, large backyard, playset, basketball hoop, pickleball net KITCHEN: Dishwasher, 6-burner gas stovetop, oven, refrigerator, microwave, cooking basics, dishware & flatware, Keurig K-Duo, percolator, coffee provided, toaster oven, beverage fridge, trash bags & paper towels GENERAL: Free WiFi, central A/C & heating, complimentary toiletries, linens & towels, in-home laundry, laundry detergent, hangers, hair dryer, keyless entry FAQ: 3 exterior security cameras (facing out) ACCESSIBILITY: 4 steps for entry, 3-story home, bedroom & full bathroom on 1st floor PARKING: Garage (2 vehicles), driveway (4 vehicles) -- THE LOCATION -- SKI RESORTS: Butternut Ski Area and Tubing Center (8 miles), Otis Ridge (9 miles), Bousquet Mountain Ski Area (19 miles), Catamount Mountain Resort (19 miles), Ski Sundown (33 miles) OUTDOOR ADVENTURES: Lake Garfield Beach (2 miles), Diane's Trail Trailhead (3 miles), Otis State Forest (8 miles), Tolland State Forest (16 miles) EXPLORE THE AREA: Berkshire Botanical Garden (13 miles), Tanglewood (15 miles), Berkshire Museum (20 miles) AIRPORTS: Bradley International Airport (43 miles), Albany International Airport (62 miles) -- REST EASY WITH US -- Evolve 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. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This 3-story home requires 4 steps for entry. While there is a bedroom and a full bathroom on the 1st floor, additional stairs are required to access bedrooms on the 2nd floor and in the basement - NOTE: Your safety matters. This property features 3 exterior security cameras: camera 1 is on the front patio facing the driveway, camera 2 is above the garage facing the driveway, and camera 3 is on the back of the house facing the yard/pool. The cameras are outward facing and do not look into interior spaces. The cameras actively record video and sound Licence number: 21382778;C0463041930

An authentic Berkshire Mountains experience awaits in Otis at this 3-bedroom, 2-bathroom vacation rental by Lindal Cedar Homes. Located close to the wandering woods and trailing waterfalls of the Otis State Forest, as well as the slopes of Butternut Ski Area, adventure can be found surrounding the cabin any time of year! When you’re ready to spend some quality time at home, curl up in the cozy living space, admire the views from the deck, or bust out a board game for some friendly competition. -- THE PROPERTY -- MassTaxConnect ID # C0396422250 | Spacious Deck | Peaceful Location | Family Friendly Bedroom 1: Queen Bed | Bedroom 2: Twin/Full Bunk Bed | Bedroom 3: Full Bed INDOOR LIVING: Smart TV, dining table, fireplace, telescope, board games, books, work desk OUTDOOR LIVING: Deck, gas grill, wooded views KITCHEN: Dishwasher, refrigerator, stove, oven, microwave, drip coffee maker, toaster, cooking basics, spices, dishware & flatware, trash bags & paper towels GENERAL: Free WiFi, central heating, complimentary toiletries, hair dryer, towels & linens, washer & dryer, iron/board FAQ: Stairs required to access, A/C: Not available, 1 Ring camera (facing driveway) PARKING: Driveway (4 vehicles) -- THE LOCATION -- HIKE & EXPLORE: Appalachian Trail (2 miles), Otis State Forest (8 miles), October Mountain State Forest (11 miles) WINTER SPORTS: Otis Ridge Ski Camp (6 miles), Butternut Ski Area and Tubing Center (18 miles), Bousquet Mountain Ski Area (18 miles), Jiminy Peak Mountain Resort (40 miles) AREA ATTRACTIONS: Naumkeag (15 miles), Berkshire Botanical Garden (16 miles), Berkshire Museum (20 miles) AIRPORT: Bradley International Airport (42 miles), Albany International Airport (61 miles) -- REST EASY WITH US -- Evolve 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. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This property does not have air conditioning - NOTE: The property requires stairs to access - NOTE: Your safety matters. This property features an exterior Ring security camera facing the driveway. The camera is outward facing and does not look into interior spaces. The camera records video and sound when activated by motion

Book your summer getaway in the Berkshires now! Hillside Haven is a contemporary and spacious family retreat, with 4 bedrooms and 3.5 bathrooms, elevated furnishings and finishes in the woods near Great Barrington and Hillsdale. Whether you’re here with family or friends, for vacation or a work getaway, you’ll find everything you need! Enjoy a large terrace with outdoor dining and grill, sunroom office, convenient workstations, and a bonus meditation or yoga room. Approaching Hillside Haven, you’re greeted by the tranquil ambiance of its prime location near Great Barrington and Hillsdale. As you step inside this 3,500-square-foot home, you’re immediately captivated by contemporary elegance and the natural serenity of the surroundings. The heart of this home is the open-plan great room, where large windows flood the space with natural light and two large sliding doors open seamlessly to the outdoor deck. Step through the glass doors and discover the perfect setting for alfresco dining, complete with a professional-grade gas grill. The bright and fully equipped kitchen boasts modern appliances and fine finishes, a large kitchen island,. Adjacent to the kitchen, the formal dining room, separated by columned archway, is perfect for intimate dinners. A sunroom off the kitchen offers a wonderful light-filled office.  Retreat to the main floor primary bedroom oasis featuring a king bed and a spa-like en-suite bath. A private study with a pull-out sofa and a screened porch provide additional spaces privacy and convenience. Upstairs, a second primary suite awaits with its own king bed, en-suite bath and a convenient work space, while two guest rooms provide two queen beds, and one king bed. A large bonus room offers the perfect space for a quiet meditation or yoga session. We’ve thought of everything to make your stay as comfortable and enjoyable as possible. Large smart TVs in the family room and master suite ensure comfort and entertainment for everyone. The fully equipped kitchen includes a coffee maker, grinder, full set of pots and pans, plates, cutlery, and basic kitchen equipment. Fresh linens, fluffy towels, and toiletries are all provided to make packing a breeze. Hillside Haven is the perfect escape for your next vacation boasting style, comfort and breathtaking natural beauty in a prime location. Let Hillside Haven be your gateway to an unforgettable Berkshire escape! Guests have the entire 2-acre property for their private use. Hillside Haven is approx. 2.5 hours from Boston and just under 3 hours from New York City. You’ll definitely need a car to get here and get around. The house has moderate cell service with AT&T and T-Mobile, but the Berkshires are full of cellular dead zones, so you may want to download the region’s online maps to your device prior to your arrival or any day tripping you do while you’re here. License number: 1-181-514-528

Chalet 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. This 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! Inside, 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. Unwind 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. Head downstairs to the basement recreation room for some friendly competition around the ping pong table. Venture 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. We’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. With 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! We 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. Chalet 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. A/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. License number: 0-917-145-376

Escape to this light-infused retreat filled with art and nestled on 6 wooded acres. Revel in captivating views of Hayes Pond, grill on the deck, then unwind to music throughout the home. This modern 2-bedroom, 3-bath vacation rental features 3 spacious decks, outdoor dining, an office with high-speed internet, a well-stocked kitchen, and luxurious bathrooms. Swim, kayak, or take the rowboat out on the pond amid herons and beavers. Hiking, dining, skiing, and cultural attractions are also nearby! -- THE PROPERTY -- MassTaxConnect ID #C0398462250 | Hayes Pond w/ Community Boat Dock Across Street | Screened-In Deck w/ Outdoor Dining Area Bedroom Suite: King Bed | Bedroom 2: Full Bed | Living Room: King Sleeper Sofa OUTDOOR LIVING: Deck, balcony w/ lounge chairs, gas grill, rowboat w/ life jackets, kayak, bicycle w/ helmet, picnic supplies, beach towels, seasonal hot tub (Memorial Day weekend-Columbus Day weekend), fishing equipment INDOOR LIVING: 2 Smart TVs, office, vaulted ceilings, skylights, ceiling fans, soaking tub, desk, wireless sound system, telescope, books, seasonal wood-burning stove (unavailable until Spring) KITCHEN: Stove/oven, refrigerator, microwave, dishwasher, dishware/flatware, cooking basics, breakfast bar, spices, coffee maker/grinder, toaster oven, blender, ice maker, water filter GENERAL: Free WiFi, central air conditioning, towels/linens, washer/dryer, complimentary toiletries, hangers, hair dryers, trash bags/paper towels, keyless entry FAQ: Step-free entry, bedrooms on 2nd and 3rd floor, 4WD recommended PARKING: Gravel driveway (4 vehicles) -- THE LOCATION -- OUTDOOR ADVENTURES: Hayes Pond (on-site), Ashintully Gardens (3 miles), Otis State Forest (4 miles), Lake Garfield Beach (6 miles), Tyringham Cobble Park (6 miles), Otis Town Beach (7 miles), Tolland State Forest (11 miles), Sandy Beach at Laurel Lake (13 miles), Lenox Town Beach (13 miles), Keystone Arches Trailhead (16 miles), Monument Mountain Parking Lot (16 miles), Granville State Forest (17 miles) SKI RESORTS: Otis Ridge Ski Resort (4 miles), Butternut Ski Area and Tubing Center (12 miles), Ski Blandford (16 miles), Bousquet Ski Area (20 miles), Catamount Mountain Resort (22 miles), Ski Sundown (30 miles) ATTRACTIONS: Shakespeare & Company (15 miles), Chesterwood Studio (15 miles), The Mount (15 miles), Norman Rockwell Museum (16 miles), Tanglewood (17 miles), Arrowhead Museum (20 miles) NEARBY CITIES: Lee (11 miles), Great Barrington (14 miles), Stockbridge (14 miles), Lenox (15 miles) AIRPORT: Bradley International Airport (39 miles) -- REST EASY WITH US -- Evolve 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. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: While the property features step-free entry, all of the bedrooms are located on the 2nd floor and 3rd floor and require stairs - NOTE: 4-wheel drive or all-wheel drive is recommended in the winter or during inclement weather - NOTE: The seasonal hot tub is only available Memorial Day weekend through Columbus Day weekend - NOTE: Fishing equipment is available and ice fishing can be done on the lake when safe - NOTE: The seasonal wood-burning stove is not available until Spring

Introducing Woodland Zen: where modern luxury meets secluded tranquility in the heart of the Berkshires. This sleek, contemporary escape will take your breath away from the moment you arrive. Surrounded by lush greenery, its modern exterior is a unique contrast with the natural landscape. Step onto your spacious deck, complete with comfortable seating and a BBQ grill, and immerse yourself in the serenity of the surrounding woodland. Floor-to-ceiling windows flood the living spaces with natural light, offering stunning views of the picturesque landscape. The bright, open living room features a large fireplace, plush seating, and a TV. Need more space? Discover a second sitting area with an additional sofa and TV. Entertain in style in the sleek dining area, nestled next to the windows and overlooking the patio. With seating for 8, it’s perfect for gatherings. Plus, there’s another dining table in the adjacent sunroom with seating for 6. Cooking is a breeze in the fully equipped kitchen, boasting stainless steel appliances, a gas range, and ample counter space. Additional barstool seating ensures everyone has a place to gather. Retreat to one of three comfortable bedrooms, each featuring a plush queen bed. The primary suite boasts an attached ensuite bathroom and access to the patio, perfect for enjoying your morning coffee in peace. Conveniently located just 10 minutes from Great Barrington, you’ll have easy access to dining, shopping, wine tasting, and outdoor adventures. With in-home laundry and parking, Woodland Zen offers the ultimate blend of luxury, privacy, and convenience for your Berkshire getaway. AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips! A visit to the Berkshires in western Massachusetts is a treat for anyone looking to pair stunning rural landscapes with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods provide a wide range of outdoor activities, from rafting and fishing in the summer to skiing and tubing in the winter. Stunning at any season, this New England region is also famous for its farm-to-table food scene and local breweries. Come see for yourself! Local Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort Home Truths: - Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request. - Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay’s approval, there is a fine of $500 per pet. Parking Details: - Parking is available onsite for 4 vehicles in the carport and driveway. - No street parking is permitted. --- The room configuration is as follows: Primary Bedroom / Queen bed w/ ensuite Bedroom 2 / Queen bed Bedroom 3 / Queen bed --- This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs. As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. There is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We’ve enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions. As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards. IDs will be requested for verification after booking. All bookings over 28 days require a security deposit. We report and prosecute all Credit Card Fraud. Licence number: C0485752830

Enjoy stunning water views and lakeside fun at this 4-bedroom + den, 4-bath vacation rental in the Berkshires. A mixture of older appliances and modern amenities, like 2 large decks and a kayak, makes this home a bright and comfortable nature retreat. Enjoy eclectic shops, galleries, and farm-to-table restaurants only a few miles away in the vibrant town of Great Barrington. Check out attractions like Tanglewood, Butternut Basin, Jacob's Pillow, museums, and bike trails on the Appalachian Trail. -- THE PROPERTY -- Permit: C0462781130 | 6 Mi to Skiing | Fireplace | Hiking, Skating, Ice Fishing, & Swimming (On-Site) | Fast EV Charger Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds | Bedroom 4: Full Bed | Den: Full Futon OUTDOOR LIVING: Gas grill, kayak, wraparound deck, lake w/ spacious dock (walking distance), walking trails nearby INDOOR LIVING: Board games, en-suite bath, flat-screen TV, jetted tub, fireplace KITCHEN: Dishwasher, microwave, stove/oven, dishware & flatware, cooking basics, toaster oven GENERAL: Linens, dryer, hair dryer, iron/board, complimentary toiletries, keyless entry, laundry detergent, towels, trash bags/paper towels, free WiFi, central heating, central air conditioning (older unit) ACCESSIBILITY: 2-story home, exterior staircase required, interior steps required to access bedrooms FAQ: Quiet hours (8:00 PM-8:00 AM), 152 steps required to reach lake (waiver may be required), gun club nearby (may occasionally hear gun shots) PARKING: Driveway (4 vehicles) -- THE LOCATION -- WINTER FUN: Butternut Ski Area and Tubing Center (6 miles), Catamount Mountain Resort (10 miles), Bousquet Mountain Ski Area (15 miles), Jiminy Peak Mountain Resort (29 miles) SUMMER SUN: Housatonic Flats Reserve (5 miles), Fountain Pond State Park (5 miles), Monument Mountain (5 miles), East Mountain State Forest (7 miles), Edith Wharton Park (13 miles), Appalachian Trail (14 miles) THINGS TO DO: Berkshire South Regional Community Center (5 miles), Norman Rockwell Museum (5 miles), Berkshire Botanical Garden (6 miles), Lee Premium Outlets (14 miles), Canyon Ranch Lenox (14 miles) AIRPORTS: Albany International Airport (51 miles), Bradley International Airport (76 miles) -- REST EASY WITH US -- Evolve 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. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This charming property is on the lake and is the perfect place to relax. This is an older property with stunning lake views - NOTE: This 2-story home requires using an exterior staircase to enter; additional interior steps are required to access the bedrooms - NOTE: Please observe quiet hours from 8:00 PM to 8:00 AM - NOTE: There are 152 steps on a long wooden staircase required to reach the dock at the lake. These stairs are not shoveled or cleared of ice in the winter. A waiver may be required before using the stairs - NOTE: There is a gun club down the road and occasionally, usually on a Sunday, you may hear gunshots - NOTE: This home offers old-fashioned appliances and quirks. While not a luxury property, it offers all the essentials for a pleasant stay!

Built in 1815 | Spacious & Serene Back Gardens Immerse yourself in a piece of South Lee history with a stay at this charming vacation rental. The unit's neighborhood is on the National Register of Historic Places, boasting a storied past, including being the birthplace of a Supreme Court justice in 1822. When you aren't exploring local galleries or hiking forest trails, relish quiet evenings by the fire or drinks in the backyard. Get ready to start your own Berkshires story — it starts here! -- THE PROPERTY -- C0195461500 INDOOR LIVING - Dining table, electric fireplace - Washer & dryer - Baseboard heating, window A/C unit OUTDOOR LIVING - Outdoor seating areas - Spacious lawn KITCHEN - Dishwasher, refrigerator, stove/oven, microwave - Drip coffee maker, Keurig, Italian press - Toaster, blender - Cooking basics, dishware & flatware ACCESSIBILITY - Single-level apartment, 2 steps to enter PARKING - Driveway (2 vehicles) -- THE LOCATION -- - 7 miles to Tanglewood - 12 miles to Jacob's Pillow - 5 miles to Norman Rockwell Museum - 7 miles to October Mountain State Forest - 15 miles to Hancock Shaker Village -- REST EASY WITH US -- Evolve 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. -- POLICIES -- - No smoking - Pet friendly w/ $75 fee (+ fees & taxes, 1 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in SECURITY CAMERA INFORMATION - 2 exterior devices - Location: front door, side of house - Coverage: driveway, side driveway, side entrance