Large group vacation rentals in Stockbridge, MA

Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house! Boasting a private deck, fireplace, in-unit laundry, and 114 acres of property to explore, this home-away-from-home can’t be beat! When you aren’t enjoying the stunning exterior space on the expansive deck or spotting wildlife like owls, foxes, and deer, venture off-site for skiing at Butternut Basin or swimming at Stockbridge Bowl. Whether snowy or sunny, endless adventures await! -- THE PROPERTY -- 1,600 Sq Ft | Pets Welcome | Free WiFi Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts retreat, complete with tranquil privacy and modern comforts. Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds OUTDOOR LIVING: Gas grill, 114 acres of hiking trails KITCHEN: Fully equipped, drip coffee maker, Keurig coffee maker, toaster, electric pancake skillet, ice cube maker, cafe table INDOOR LIVING: 2 TVs, HD TV, fireplace, dining table, Apple Mac-Mini computer, cell phone charging station GENERAL: Washer & dryer, towels, linens, complimentary toiletries, central air conditioning/heat, keyless entry, pet fee (paid pre-trip) SUITABILITY: Stairs required PARKING: Driveway (2 vehicles), detached garage (1 vehicle), outdoor area (1 vehicle) -- THE LOCATION -- STOCKBRIDGE BOWL (4.0 miles): Stockbridge Town Beach, BSO Beach, Stockbridge Bowl Boat Ramp, boating, swimming, fishing, kayaking, paddle boarding, canoeing HIKING: 114 acres on-site, Stevens Glen Trail Head (4.8 miles), Monument Mountain Reservation (4.8 miles), Olivia's Overlook (5.5 miles), Brothers Trail (6.0 miles), Burbank Trail (6.2 miles), Parsons Marsh Reserve (6.5 miles), Appalachian Trail (12.1 miles) LOCAL ATTRACTIONS: Norman Rockwell Museum (1.4 miles), Orleton Farm (3.7 miles), Tanglewood (5.6 miles), Koussevitzky Music Shed (5.8 miles), Seiji Ozawa Hall (6.7 miles), Frelinghuysen Morris House & Studio (6.7 miles), The Playhouse (6.9 miles), Ventfort Hall Mansion and Gilded Age (7.4 miles), The Mount, Edith Wharton's Home (7.5 miles) SKIING: Ski Butternut (9.9 miles), Catamount Mountain Resort (14.6 miles), Jiminy Peak Mountain Resort (25.8 miles) AIRPORT: Albany International Airport (48.0 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 -- - Massachusetts Tax ID: C0214960870 - No smoking - Pet friendly w/ $75 fee (+ fees & taxes, maximum 3 pets allowed) - No events, parties, or gatherings of more than 6 people - No fireworks allowed on the property - Garage is unavailable during winter months (11/15-4/15) - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: Access to the home requires stairs Licence number: C0214960870

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

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

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

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

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

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

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

High-Speed WiFi | Upgraded Kitchen | Private Forest-View Balcony | 2010 Addition to 1738 Property Kick off your next Berkshire getaway at this Lee vacation rental, where historic soul meets modern luxury! The 2-bed, 1-bath apartment serves as a launchpad for the arts and adventure — wake up to serene views before hiking the AT, fishing, or browsing the Norman Rockwell Museum. After an evening performance at Tanglewood, return home to recharge in style. Secure this New England sanctuary today! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed - Additional Sleeping: 1 portable crib APARTMENT FEATURES - Balcony - Smart TV, board games - Electric fireplace - 2010 addition to historic property built in 1738 KITCHEN - Refrigerator, stove/oven, dishwasher - Drip coffee pot, French press (starter coffee provided) - Toaster oven, microwave - Cooking basics, dishware & flatware - Spices - 4-person dining table, counter seating, high chair GENERAL - Free WiFi (300 Mbps) - Central A/C & heating, ceiling fan - Washer & dryer, iron/board - Linens & towels - Complimentary toiletries, hair dryer, hangers - Keyless entry FAQ - 1 exterior security camera (facing driveway) ACCESSIBILITY - Single-story apartment - 1 interior flight of stairs to access PARKING - Driveway (1 vehicle) -- THE LOCATION -- - 0.9 miles to downtown Lee - 2 miles to Lee Premium Outlets - 4 miles to Stockbridge, famous for Norman Rockwell's 'Street Scenes' - 4 miles to Goose Pond Reservation & October Mountain State Forest - 11 miles to Jacob's Pillow - 55 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 ADDITIONAL INFORMATION - This single-story apartment requires 1 interior flight of stairs to access - Your safety matters. This property features 1 exterior security camera located outside the front door facing the driveway. It is outward facing and does not look into any interior spaces. The camera actively records audio and video Licence number: C0195461500;C0195461500;C0550811500;C0550811500;C0195461500;C0550811500;C0195461500

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!