Large group vacation rentals in Otis, MA

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

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

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

Built in 1974 | Private Acreage & Scenic Surroundings | Fireside Relaxation | EV Charger Embrace a slower pace of life at this inviting 2-bedroom, 1-bath vacation rental in Becket! Set on 4 wooded acres, this rustic retro-inspired cabin offers a peaceful outdoorsy retreat with all the comforts of a work-from-home stay. Walk to the community lake or venture out to Chester-Blandford State Forest. As evening falls, settle into the hammock and ignite the gas grill for a memorable barbecue! -- THE PROPERTY -- C0443750220 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Living Room: 1 queen sleeper sofa INDOOR LIVING - Smart TV, stereo - Duraflame fireplaces (bedrooms) - Avocado organic mattresses w/ Westin Heavenly mattress pads (bedrooms), hammock - Bluetooth speaker OUTDOOR LIVING - Deck w/ seating - Private yard, hammock, games, grill KITCHEN - Refrigerator, stove/oven, microwave - Drip & Keurig coffee makers - Toaster oven, spices - Cooking basics, dishware & flatware GENERAL - Free WiFi (high speed) - Floor + table fans, ceiling fans - Baseboard heating & space heaters - Window A/C units (new 2025, living room & both bedrooms) - Linens & towels, iron/board FAQ - Pet fee (paid pre-trip) - Under renovations in July (no work during guest stays) ACCESSIBILITY - 2-story home, stairs required for entry - All bedrooms on 2nd floor - Child gates (top & bottom of stairs) PARKING - Driveway (4 vehicles) -- THE LOCATION -- - Quiet area, close to ponds & hiking trails - 9 miles to Appalachian Trail & Otis Ridge - 11 miles to Chester-Blandford State Forest - 18 miles to Berkshire Museum - 19 miles to Ski Blandford - 40 miles to Bradley Int’l Airport & Albany Int’l 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 - Pet friendly w/ $50 fee (+ fees & taxes) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story property requires stairs to enter and interior stairs to access all bedrooms - Only the main floor fireplace is available for guest use. Detailed instructions are in the house book at the property - The house will be undergoing renovations in July. Work will not be happening while guests are present; however, you may see paint cans, ladders, etc, during your stay

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

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

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

Great for Families | 11 Wooded Acres | Boat Dock | Furnished Sunroom | 2 Fire Pits Whether you’re seeking thrilling outdoor adventures or quality time with loved ones, you’ll find a beautiful escape at this 3-bed, 3-bath vacation rental in the Berkshires! Sip your coffee on the patio while soaking in the pond views, then hike the Appalachian Trail or hit the slopes at Bousquet Mountain. Ready to recharge? Retreat to one of the living areas to relax by the fire. Book your Western Mass getaway! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 full bed, 1 twin bed, 1 twin sleeper sofa OUTDOOR LIVING - Patio w/ dining area - Charcoal grill - 2 fire pits - Garden - Boat dock, pond access INDOOR LIVING - 2 Smart TVs, DVD player - Wood-burning fireplace, wood-burning stove - Expansive windows, natural light - Furnished sunroom - Dining table - Board games, books KITCHEN - Refrigerator, dishwasher, electric stovetop, microwave - Keurig coffee maker (coffee provided) - Spices, toaster, blender - Cooking basics, dishware & flatware GENERAL - Free WiFi - Central heating - Washer & dryer, iron/board, laundry detergent - Linens, towels - Beach chairs/umbrella/towels - Hair dryer FAQ - No A/C ACCESSIBILITY - Single-story home, stairs to enter PARKING - Driveway (3 vehicles) -- THE LOCATION -- - Peaceful location near outdoor recreation: 9 lakes, watersports, renowned spas, golf courses, skiing, hiking - 6 miles to Appalachian Trail - 8 miles to Otis Ridge Ski Camp - 12 miles to October Mountain State Forest - 15 miles to Naumkeag - 17 miles to Berkshire Botanical Garden & Berkshire Museum - 19 miles to Bousquet Mountain Ski Area - 20 miles to Butternut Ski Area and Tubing Center - 42 miles to Bradley Int’l Airport, 63 miles to Albany Int’l 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 - This single-story home requires stairs to enter - The property does not have air conditioning Licence number: C0258520220

Experience the beauty of the Berkshires from Cordelia, your charming Massachusetts home with a chic cottage style and romantic outdoor spaces. Head to the backyard to find a brick patio and picturesque dining table that makes setting up an Insta-worthy spread a breeze. Gather around the firepit, doze off in the hammock, or play a round of cornhole in the yard. Inside, Cordelia welcomes you with a fireplace and TV in the front living room, a formal dining room, and a country-style kitchen with unique antique pieces. Spread out between five bedrooms before grabbing a glass of wine for a soak in the clawfoot tub upstairs. When you’re ready, the Berkshires are packed with more outdoor activities, views, hikes, museums, and art exhibits than you could ever hope to see in one visit. We hope that means we’ll be welcoming you more than once! 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! Local Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort Visiting the Berkshires is a must for anyone looking to pair a gorgeous natural landscape with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods here makes it easy to enjoy a wide range of outdoor activities, from rafting and fishing to ziplining and hiking. Stunning in any season, this region is famous for its food scene, which values local ingredients, and you’ll find many farm-to-table establishments in the southern areas. Explore classic New England architecture, a growing array of performing arts, and dozens of towns and trails. The Berkshires are waiting with variety and beauty you won’t find anywhere else. Home Truths: - This home allows pets for a fee. If undisclosed pets are brought into the home without AvantStay’s approval there is a fine of $500 per pet. - This home does not have AC. - 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. ​​​​​​​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 w/ ensuite Bedroom 2: Queen bed Bedroom 3: Queen bed Bedroom 4: King bed Bedroom 5: 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 30 days require a security deposit. We report and prosecute all Credit Card Fraud. Licence number: C0399231500

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

Steps to Main Street | 2 Mi to Tanglewood | Private Yard w/ Grill This Lenox vacation rental places you in the heart of the Berkshires! Steps from shops and restaurants and minutes from Tanglewood, you’ll enjoy easy access to world-class arts, culture, and outdoor adventure. The 3-bedroom, 2.5-bath home is also conveniently located within a short drive of the Appalachian Trail and ski resorts. After exploring, relax with a backyard barbecue or unwind inside with all the comforts of home. -- THE PROPERTY -- C0514291520 SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 full bed STEP OUTSIDE - Private yard w/ gas grill - Front yard w/ garden INDOOR LIVING - Hardwood flooring - Smart TVs - Natural sunlight KITCHEN - Refrigerator, stove/oven, dishwasher, microwave - Drip coffee maker, toaster oven - Cooking basics GENERAL - Free WiFi - Central heating & A/C - Linens & towels, complimentary toiletries FAQ - Quiet hours (10:00 PM-8:00 AM) ACCESSIBILITY - 2-story home, 3 steps to enter PARKING - Designated parking spaces (2 vehicles) - Additional vehicles must be parked in public parking (not at the nearby inn) -- THE LOCATION -- - Close to hiking trails, skiing resorts & golf courses - 2 miles to The Mount, Edith Wharton's Home - 5 miles to Bousquet Ski Area - 10 miles to Fountain Pond State Park - 13 miles to Appalachian Trail - 51 miles to Albany 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 - Please observe quiet hours from 10:00 PM and 8:00 AM ADDITIONAL INFORMATION - This 2-story home requires 3 steps to enter Licence number: C0020201520;C0514291520;LENOX SHORT TERM RENTAL REGISTRATION

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

Experience historic charm and colonial beauty when you cross the threshold into this 3-bedroom, 2-bath Huntington vacation rental. This house, built in 1789, still boasts many of the original furnishings, providing a memorable New England retreat that you won't find elsewhere! Enjoy modern amenities, too, including air conditioning, plush beds, and a DVD player with a large movie collection! You will be right across from a swimming hole, surrounded by forests, and near the Appalachian Trail! -- THE PROPERTY -- MassTaxConnect ID #: C0295701430 | 3,000 Sq Ft | Free WiFi Leave it to Massachusetts to provide the most charming historic home, the perfect spot for families or friend groups looking for an antique feel combined with easy access to nature. Bedroom 1 (Chester Room): Queen Bed | Bedroom 2 (Skyline Road): Full Bed | Bedroom 3 (Back Room): 2 Twin Beds | Living Room: Sleeper Sofa OUTDOOR LIVING: Large backyard, wooded views, river access MODERN AMENITIES: TV, DVD player, books, ceiling fans, 6-person dining table HISTORIC TOUCHES: Original wood flooring, wood-burning fireplaces, antique furniture, clawfoot tub KITCHEN: Fully equipped, tea kettle, toaster, toaster oven, Keurig coffee maker, dishware/flatware GENERAL: Washer & dryer, linens, towels, beach towels, hair dryer, A/C in all bedrooms FAQ: Stairs required for access PARKING: Driveway (5 vehicles) -- THE LOCATION -- EXPLORE NATURE: Sanderson Brook Waterfall (2.8 miles), Goldmine Brook Falls (3.0 miles), C.M. Gardner State Park (4.6 miles), Chester Becket Railroad Trailhead (5.8 miles), Huntington State Forest (7.4 miles), Becket Quarry (9.3 miles), Appalachian Trail (17.1 miles), Otis Ridge (18.2 miles), October Mountain State Forest (23.6 miles) LOCAL FARE: Comfort Kitchen & Bar (2.0 miles), The Rapids Bar & Grill (5.1 miles), Chester Common Table (5.6 miles), Russell Inn (5.7 miles), Red Lion Inn (26.4 miles) MUSIC: The Iron Horse Music Hall (17.8 miles), Pearl Street - Northampton (18.0 miles), Tanglewood - Lenox (27.3 miles) AIRPORT: Bradley International Airport (31.8 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: The property requires stairs and may be difficult for guests with limited mobility Licence number: C0295701430;C0295701430

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

Situated in the heart of the Berkshires, this 3-bed, 2-bath vacation rental offers a modern living space, a large yard and an ideal location near many attractions. Adventure seekers will enjoy easy access to the Appalachian Trail and Catamount Ski Resort, music fans can catch the Boston Symphony Orchestra (BSO) at Tanglewood and theater lovers will be minutes from Shakespeare & Co and Barrington Stage Co. No matter what you’re seeking, this Lenox home will offer something nearby to enjoy! -- THE PROPERTY -- MassTaxConnect ID C0219571520 | 2,457 Sq Ft | Off-Street Parking | 2 Mi to Appalachian Trail Bedroom 1: King Bed | Bedroom 2: 2 Extra Long Twin Beds | Bedroom 3: 2 Extra Long Twin Beds | Family Room: Sleeper Sofa KITCHEN: Fully equipped, cooking basics, spices, coffee maker, blender, dishwasher, Crockpot, microwave, high-chair, wooden cabinets INDOOR LIVING: Furnished sunroom, flat-screen smart cable TV, DVD player, books, hardwood floors, decorative fireplace, 6-person dining table, 4-person glass table OUTDOOR LIVING: Large private yard, outdoor seating, Weber gas grill GENERAL: Free WiFi, towels/linens, toiletries, ceiling fans, hair dryer, keyless entry, first aid kit, window air conditioning units in each bedroom, portable air conditioning unit in living area PARKING: Garage (2 small vehicles), driveway (4 vehicles) -- THE LOCATION -- MUSIC & THEATRE: Shakespeare and Company (3.0 miles), Tanglewood Music Center (3.7 miles), Boston Symphony Orchestra (3.7 miles) Jacob’s Pillow (15.0 miles) POPULAR ATTRACTIONS: Kripalu Center for Yoga & Health (4.6 miles), Norman Rockwell Museum (8.8 miles), Berkshire Botanical Gardens (7.9 miles), Cranwell Spa & Golf Resort (3.7 miles) OUTDOOR ACTIVITIES: Appalachian Trail (11.2 miles), Pleasant Valley Wildlife Sanctuary (2.1 miles), Lenox Mountain (8.2 miles), Sandy Beach at Laurel Lake (5.4 miles), October Mountain State Forest (5.4 miles), Woods Pond (4.8 miles), Kennedy Park (2.7 miles), Stockbridge Bowl (5.6 miles) WINTER ACTIVITIES: Catamount Ski Area (23.4 miles), Bousquet Ski Area (5.1 miles), Ski Butternut (16.6 miles), Otis Ridge (18.9 miles) NEARBY CITIES: Lenox Center (2.3 miles), Great Barrington (15.8 miles), Stockbridge (9.0 miles), Pittsfield (7.7 miles), Sheffield (22.1 miles), Williamstown (27 miles) AIRPORTS: Albany International Airport (49.5 miles), Bradley International Airport (71.1 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: Additional post-stay fines will be imposed if travelers exceed the maximum occupancy of 6 Licence number: C0219571520;C0219571520

Escape to a lake retreat with this 3-bedroom, 2-bathroom vacation rental home in Stockbridge. Stockbridge Bowl's grassy beach is just a short walk away, promising days of fun boating, swimming, and kayaking on the water. For entertainment on dry land, explore the nearby Koussevitzky Music Shed or Norman Rockwell Museum. There's more outdoor fun to be had on various hiking trails located within 5 miles or less! After a long day, relax on the screened-in porch with a home-cooked meal. -- THE PROPERTY -- MassTaxConnect ID C0372932830 | Free WiFi | Walk to Lake | Family Friendly | 0.2 Miles to Beach Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Twin Bed w/ Twin Trundle Bed INDOOR LIVING: Fireplace, Smart TV, washer/dryer OUTDOOR LIVING: Screened-in porch, gas grill (propane provided), seating KITCHEN: Stainless steel appliances, gas range, coffee maker, dishware & flatware GENERAL: Keyless entry, complimentary toiletries, towels & linens, central heating FAQ: 2 exterior security cameras (facing driveway and side of home), stairs required for access PARKING: Driveway (3 vehicles) -- THE LOCATION -- STOCKBRIDGE BOWL: Stockbridge Town Beach (0.2 miles - 10-min. walk), BSO Beach (1.8 miles), Stockbridge Bowl Boat Ramp (2.6 miles), boating, swimming, fishing, kayaking, paddle boarding, canoeing OUTDOOR EXPLORATION (< 5 miles): Brothers Trail, Parsons Marsh Reserve, Olivia's Overlook, Burbank Trail, Stevens Glen Trail Head, Butternut Ski Area and Tubing Center LOCAL ATTRACTIONS (< 5 miles): Koussevitzky Music Shed, Seiji Ozawa Hall, Frelinghuysen Morris House & Studio, Tanglewood, Ventfort Hall Mansion and Gilded Age, Norman Rockwell Museum, Chesterwood, Berkshire Theatre Group, Barrington Stage Company AIRPORT: Albany International Airport (49.8 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: Your safety matters. This property features 2 exterior security cameras located on the screened-in porch and side of the home, facing outward. They do not look into any interior spaces. The cameras record video and sound when activated by motion. They will record when they first sense motion and 30 seconds after the last motion is detected - NOTE: The property requires stairs to access Licence number: C0372932830

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

Experience a fun-filled group getaway at this Pittsfield vacation rental! Named 'The Duchess of Pomeroy' for its charming historical features, this 5-bedroom, 3.5-bath home boasts a furnished deck, a foosball table, and a screened porch that's perfect for enjoying morning coffee or evening cocktails. Looking to venture out? Catch live music at Tanglewood or shred the slopes at Bousquet Mountain Ski Area. Afterward, cook a meal on the grill and dine al fresco. A memorable stay awaits! -- THE PROPERTY -- C0344732360 | Gas Grill | 8 Mi to Tanglewood | Fully Equipped Kitchen w/ Food | 2,718 Sq Ft Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Twin Bed | Bedroom 5: Full Bed | Additional Sleeping: Twin Rollaway Cot OUTDOOR LIVING: Private yard, screened porch, outdoor dining areas, deck, picnic supplies w/ cooler blanket, ice packs, recyclable cutlery, bug spray & umbrella INDOOR LIVING: Smart TV, laptop-friendly workspace, dining table, board games, books, 4-in-1 game table (foosball, ping-pong, air hockey, billiards), fireplace, piano, 2 staircases, butler's pantry KITCHEN: Cooking basics, dishwasher, blender, Keurig & drip coffee makers, complimentary coffee beans, pods & tea, coffee grinder, 2 Crockpots, dishware & flatware, microwave, ice maker, toaster, spices, water filter GENERAL: Free WiFi (146.6 Mbps), A/C units (every bedroom + living room), central heating, towels/linens, hair dryer, hangers, in-unit washer/dryer, complimentary toiletries, iron/board, distilled water (for iron) FAQ: Garage not available for guest use ACCESSIBILITY: 3-story home, exterior stairs required to enter, all bedrooms on 2nd & 3rd floors PARKING: Driveway (4 vehicles), free street parking -- THE LOCATION -- ATTRACTIONS: Colonial Theatre (0.4 miles), Berkshire Museum (0.5 miles), Kidding Around Consignment (1 mile), Lake Onota (3 miles), Pittsfield State Forest (6 miles), Tanglewood (8 miles), TurnPark Art Space (11 miles), Notchview Nature Preserve (14 miles), Clark Art Institute (21 miles), Mohawk Trail (36 miles) RESTAURANTS: District Kitchen & Bar (0.6 miles), Thistle & Mirth (0.6 miles), King Kone (0.6 miles), Crust Pizza (0.6 miles), Trattoria Rustica (0.7 miles), Dottie's Coffee Lounge (1 mile), La Fogata (2 miles), Proprietor's Lodge (4 miles) SKI RESORTS: Bousquet Mountain Ski Area (4 miles), Jiminy Peak Mountain Resort (12 miles) AIRPORTS: Albany International Airport (43 miles), Bradley International Airport (59 miles), Hartford–Brainard Airport (65 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 or vaping of any kind - No pets allowed - No events, parties, or large gatherings - No candles or incense inside the house. A citronella candle outside is allowed and found on the back deck to help shoo away mosquitoes - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This 3-story home requires exterior stairs to enter. All bedrooms are located on the 2nd and 3rd floors and require additional interior stairs to access - NOTE: This property sleeps 9 guests in 5 beds, with room for 10 total by using the twin rollaway cot - NOTE: The garage is not available for guest use - NOTE: WiFi speed: 146.6 Mbps download, 17.1 Mbps upload, 29ms latency - NOTE: The owner provides milk, fruit, bread, butter, peanut and almond butter, jam, and various coffee and teas. Various staples are also provided in the pantry. Let the Guest Contact know of any food allergies in your group so the food available can be adjusted to your greatest welfare Licence number: C0344732360

Crossbridge is a spacious 4 bed, 5 bath property 2.5 hrs from Boston & under 3 hrs from NYC. It is a beautiful private property of 25 acres inclusive of a pond, gazebo, vegetable garden and walking trails featuring a turreted structure, wooden accents, stone brick walls, several fireplaces, large windows & multiple laptop friendly work spaces. Nearby towns: Stockbridge(10mins), Lee(15mins), Great Barrington(20mins), Catamount Ski Mountain(25mins) This charming historic home blends classic New England architecture with unique character featuring a beautiful turreted structure, welcoming covered porch and multiple dormer windows that frames a cozy, light-filled interior. From the mudroom, climb the spiral staircase to access the main house to the right. Main House: With its rustic charm, the sun room offers rich polished wood floors, a matching wooden staircase with metal railings and large industrial-style windows to fully take in the views. The décor combines contemporary and vintage elements including cozy seating, a wooden armoire, potted plants and pendant globe lighting enhancing the room’s natural tones. In the bright and cozy TV room is a vaulted ceiling with a skylight, large windows framed in dark wood offering picturesque views, neutral toned sofas arranged around a lucite coffee table atop a soft patterned area rug. A welcoming open-plan living and dining area offers comfortable seating by large windows, a round dining table for six and two fireplaces while the fully equipped kitchen boasts a lovely stone brick wall pizza oven, white cabinetry with brass handles, soapstone countertops and stainless steel appliances. There are three bedrooms on the upper floor of the main house each with its own ensuite bathroom. Two bedrooms are accessible via one staircase, while the third is reached by a separate staircase.The primary bedroom is spacious, featuring a king bed positioned in front of large windows, beautiful wooden floors, a dresser, decorative fireplace and ample seating including a rocking chair while the ensuite bathroom boasts a separate bathtub and shower. The twin bedroom features a wooden desk plus chair, chest of drawers, single chair and its ensuite bathroom includes a walk-in shower while the queen bedroom offers a laptop-friendly workspace, a plush red sofa and dresser. Its ensuite bathroom has a combined tub and shower. On the main level, the lively yellow bedroom features a decorative fireplace, laptop-friendly workspace, comfy chairs, expansive windows and a bookcase filled with a range of books. The ensuite bathroom is a striking royal blue with a large walk-in shower. Surrounded by stunning wooded landscapes, this private retreat offers rustic charm with modern potential—ideal for those seeking a peaceful getaway or quality time with close family and friends. Crossbridge is the perfect retreat for relaxation while enjoying the scenic outdoor views. Please Note: There is a 2-bedroom apartment located just up a few stairs to the left as you enter from the main entrance. This apartment is not included in your rental and will remain closed off during your stay. If you’re interested in renting the full 6-bedroom property, including the apartment, please inquire for availability and pricing. Guests do not have access to the garage. Guests do not have access to the piano. It is locked as it is very fragile. Crossbridge is approx. 2.5 hours from Boston and under 3 hours from New York City. You’ll definitely want a car to get there and around the area. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. 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 house. Please Note - No parties or large gatherings are allowed License number: C0161493260

Crossbridge is a spacious 6 bed, 7 bath property 2.5 hrs from Boston & under 3 hrs from NYC featuring a main house with 4 beds and an apartment with 2 beds. It is a beautiful private property of 25 acres inclusive of a pond, gazebo, vegetable garden and walking trails featuring a turreted structure, wooden accents, stone brick walls, several fireplaces, large windows & multiple laptop friendly work spaces. Nearby towns: Stockbridge(10mins), Lee(15mins), Great Barrington(20mins), Catamount Ski Mountain(25mins) This charming historic home blends classic New England architecture with unique character featuring a beautiful turreted structure, welcoming covered porch and multiple dormer windows that frames a cozy, light-filled interior. From the mudroom, climb the spiral staircase to access the main house to the right or the apartment to the left. Main House: With its rustic charm, the sun room offers rich polished wood floors, a matching wooden staircase with metal railings and large industrial-style windows to fully take in the views. The décor combines contemporary and vintage elements including cozy seating, a wooden armoire, potted plants and pendant globe lighting enhancing the room’s natural tones. In the bright and cozy TV room is a vaulted ceiling with a skylight, large windows framed in dark wood offering picturesque views, neutral toned sofas arranged around a lucite coffee table atop a soft patterned area rug. A welcoming open-plan living and dining area offers comfortable seating by large windows, a round dining table for six and two fireplaces while the fully equipped kitchen boasts a lovely stone brick wall pizza oven, white cabinetry with brass handles, soapstone countertops and stainless steel appliances. There are three bedrooms on the upper floor of the main house each with its own ensuite bathroom. Two bedrooms are accessible via one staircase, while the third is reached by a separate staircase.The primary bedroom is spacious, featuring a king bed positioned in front of large windows, beautiful wooden floors, a dresser, decorative fireplace and ample seating including a rocking chair while the ensuite bathroom boasts a separate bathtub and shower. The twin bedroom features a wooden desk plus chair, chest of drawers, single chair and its ensuite bathroom includes a walk-in shower while the queen bedroom offers a laptop-friendly workspace, a plush red sofa and dresser. Its ensuite bathroom has a combined tub and shower. On the main level, the lively yellow bedroom features a decorative fireplace, laptop-friendly workspace, comfy chairs, expansive windows and a bookcase filled with a range of books. The ensuite bathroom is a striking royal blue with a large walk-in shower. The Apartment: This cozy, open-concept living space includes a kitchen and a sitting area with a rustic and cottage-like charm, vaulted ceilings with exposed wooden beams and large windows framed in light wood. The kitchen presents white cabinetry with a bright green accent wall and a black metal pot rack hangs from the ceiling, enhancing the kitchen’s rustic aesthetic. The living area is furnished with blue-striped sofas and armchairs, a woven natural fiber rug and a small wooden entertainment stand with TV. A built-in bookshelf, filled with a diverse collection of books, is neatly tucked under the wooden staircase, contributing to the home’s cozy and inviting atmosphere. This apartment offers two bedrooms, each with an ensuite bathroom. The primary bedroom, located upstairs, features a king-size bed, a chest of drawers and a single chair, a separate workspace area and its sleek black ensuite bathroom boasts a large walk in shower. Downstairs, to the left of the wooden staircase, is the queen bedroom. Soft lavender-coloured walls create a soothing ambiance, complemented by a small wooden nightstand, dresser, and sliding glass doors that lead to the back deck. The attached bathroom is designed with beige tiles and includes a combined tub and shower. Surrounded by stunning wooded landscapes, this private retreat offers rustic charm with modern potential—ideal for those seeking a peaceful getaway or quality time with close family and friends. Crossbridge is the perfect retreat for relaxation while enjoying the scenic outdoor views. Guests do not have access to the garage. Guests do not have access to the piano. It is locked as it is very fragile. Crossbridge is approx 2.5 hours from Boston and under 3 hours from New York City. You’ll definitely want a car to get there and around the area. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. 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 house. Please Note - No parties or large gatherings are allowed License number: C0161493260

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

Welcome to Beaver Creek by AvantStay! Tucked amid the rolling hills and vibrant forests of Stockbridge, Beaver Creek is a storybook escape where New England charm meets modern comfort. This picturesque retreat sits surrounded by lush gardens and autumn-kissed scenery, offering a front-row seat to the Berkshires’ beauty—just minutes from the serene Stockbridge Bowl, historic Main Street, and cultural icons like Tanglewood and the Norman Rockwell Museum. Step inside to discover bright, inviting interiors that balance timeless elegance with relaxed comfort. The living room, wrapped in soft whites and natural light, centers around a cozy wood-burning fireplace—perfect for gathering after a day exploring nearby trails or art galleries. Adjacent, the dining room seats eight for memorable meals, while the fully equipped kitchen makes entertaining easy with its modern finishes and sunny window views. Four serene bedrooms promise peaceful rest, including two spacious king suites and a cheerful bunk room ideal for kids or friends. The primary suite offers a spa-like ensuite bath with a soaking tub and walk-in shower, while an additional full bathroom and half bath ensure comfort for all. Outdoors, you’ll find every reason to linger—from morning coffee on the covered porch to sunset barbecues in the crisp mountain air. The patio features a grill, picnic table, and lounge seating for six, surrounded by manicured landscaping and views that shift beautifully with the seasons. Whether you’re leaf-peeping in the fall, skiing at nearby resorts in the winter, or soaking in lake breezes come summer, Beaver Creek invites you to experience the best of the Berkshires in style and serenity. 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. Visiting the Berkshires is a must for anyone looking to pair a gorgeous natural landscape with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods here makes it easy to enjoy a wide range of outdoor activities, from rafting and fishing to ziplining and hiking. Stunning in any season, this region is famous for its food scene, which values local ingredients, and you’ll find many farm-to-table establishments in the southern areas. Explore classic New England architecture, a growing array of performing arts, and dozens of towns and trails. The Berkshires are waiting with variety and beauty you won’t find anywhere else. Local Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort. Visit High Lawn Farm, a beloved local creamery known for its farm-fresh ice cream, handcrafted cheeses, and artisanal dairy made right in the Berkshires. 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. - The property uses well water, which is safe for consumption and daily use. - The home operates on a septic system, so please avoid flushing anything other than toilet paper. - A static lock code provides access to both the main gate and the house. - Firewood is not provided; please bring your own if you plan to use the fireplace or fire pit. - This home is located on a working farm, so guests may notice occasional farm activity such as tractors, planting, and harvesting. - Local wildlife may be present in the area, so please enjoy with care and keep food securely stored. - A pack ’n play and high chair are available for guest use. Parking Details: - Parking is available in the driveway for up to 6 vehicles; the garage is not accessible, but there are no neighborhood parking restrictions. All bookings over 30 days require a security deposit to be charged after booking. 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: C0533330700

Dive into the rich culture, adventure, and beauty of the Berkshires with this Lake Ashmere vacation rental cottage! Inside, everyone will find a space of their own within the 3-bed, 2-bath property. Step onto the furnished outdoor deck to revel in the sweeping water views, fire up the grill for an afternoon BBQ, or get competitive with a family volleyball game on the lawn! When you're not splashing around in the lake, get out and explore the best of the Berkshires, all within an hour's drive! -- THE PROPERTY -- MassTax ID C0257771320 | Central A/C | 1,340 Sq Ft | Access to Private Association Beach & Picnic Area Bring the family to experience a slice of the lake life at this newly updated and furnished Hinsdale cottage, equipped with all the outdoor living essentials and a convenient location within easy reach of famous Berkshire attractions - the perfect home base for your next retreat to Massachusetts' highlands! Bedroom 1: Queen Bed | Bedroom 2: 2 Twin Beds | Bedroom 3: Queen Bed OUTDOOR LIVING: Direct Ashmere Lake access, private sand beach, water-facing deck furnished w/ patio set & gas grill, private dock for swimming & fishing, spacious yard, kayaks & paddleboat KITCHEN: Fully equipped, dishware/flatware, blender, toaster, drip coffee maker, dishwasher INDOOR LIVING: Flat-screen cable TV, tiled sun porch w/ lake views, easy-access main floor master bedroom GENERAL: Free WiFi, linens/towels, laundry machines, trash bags, paper towels, beach chairs & towels, hair dryer FAQ: Stairs required for access, strict maximum occupancy of 6, no fence before lake PARKING: Off-street parking -- THE LOCATION -- SUMMER ACTIVITIES: Picnic concerts at Tanglewood (19.0 miles), Pittsfield Suns games at Wahconah Park (11.7 miles), Hancock Shaker Village (16.1 miles), Pleasant Valley Sanctuary (16.6 miles) OUTDOOR RECREATION: Burbank Park (12.9 miles), Lulu Brook (15.9 miles), Pontoosuc Lake (12.2 miles), Wahconah Falls State Park (5.8 miles), Bousquet Ski Area (14.7 miles), Jiminy Peak Mountain Resort (18.8 miles) MUSEUMS: Clark Art Institute and Museum (28.0 miles), Berkshire Art Museum (23.4 miles), MASS MoCA (24.0 miles), Animagic Museum of Animation (21.1 miles), Baseball in the Berkshires (10.1 miles) PERFORMING ARTS: Boston Symphony Orchestra (19.0 miles), Albany Berkshire Ballet (10.7 miles), Barrington Stage Company (11.3 miles), Aston Manga Music Festival (31.0 miles) SHOPPING: Dory & Ginger (11.0 miles), Stockbridge boutiques (24.3 miles), Lee Premium Outlets (21.7 miles) AIRPORT: Albany International Airport (~58.7 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 - Strict maximum occupancy of 6 - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This property requires stairs to access - NOTE: Because this is a 72-foot lakefront property with a dock and a lot of stairs, the property might not be suitable for young children; adult supervision is recommended Licence number: C0257771320

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