Large group vacation rentals in Lenox, MA

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

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

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

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

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

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

Just minutes from downtown Pittsfield and surrounded by the beauty of the Berkshires is this lovely 5-bedroom, 2-bathroom vacation rental! Immerse yourself in the arts, wander around history, take a hike, or enjoy the local bites — all possible from this convenient location. After your day around town, come back to this home and sit and enjoy a show in front of the fireplace, take a soak in the soaker tub, or whip up a delicious meal in the large kitchen. -- THE PROPERTY -- MassTaxConnect ID #C0404362360 | 7 Mi to Tanglewood | Grill | Covered Porch Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Full Bed | Bedroom 4: Queen Bed | Bedroom 5: Twin Bed INDOOR LIVING: Fireplace, Smart TV, dining table, ceiling fans, board games, books, laptop friendly, soaker tub KITCHEN: Refrigerator, stove/oven, microwave, dishwasher, drip coffee maker, toaster, dishware & flatware, spices, cooking basics GENERAL: Free WiFi, washer & dryer, towels, linens, complimentary toiletries, central heat, window A/C units, keyless entry, hair dryer, hangers, trash bags/paper towels FAQ: 3 exterior security cameras (facing out), stairs are required, pet fee (paid pre-trip, dogs only, 2 max) PARKING: Driveway (2 vehicles), street parking (first-come, first-served) -- THE LOCATION -- THE ARTS: Colonial Theatre (0.6 miles), Barrington Stage Company (1 mile), Boston Symphony Orchestra (7 miles), Shakespeare & Company (7 miles), Tanglewood Performing Arts (8 miles), Kripalu Center For Yoga & Health (9 miles), Jacob's Pillow (19 miles), Aston Magna Music Festival (20 miles), Albany Berkshire Ballet (38 miles) MUSEUMS: Berkshire Art Museum (0.4 miles), Herman Melville's Arrowhead (2 miles), The Mount - Edith Wharton’s Home (9 miles), Animagic Museum of Animation (10 miles), Norman Rockwell Museum (13 miles), MASS MoCA (21 miles), Clark Art Institute & Museum (21 miles) OPT OUTSIDE: Burbank Park (1 mile), Pontoosuc Lake (3 miles), Wahconah Falls State Park (8 miles), Mount Greylock State Reservation Visitor Center (9 miles), Ashmere Lake (10 miles), Monument Mountain (16 miles) SUMMER ACTIVITIES: Pittsfield Suns at Wahconah Park (1 mile), Hancock Shaker Village (4 miles), Mass Audubon's Pleasant Valley Wildlife Sanctuary (5 miles) AIRPORT: Albany International Airport (47 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 - Dog friendly w/ $100 fee (+ fees & taxes, 2 max) - 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 for access - NOTE: Your safety matters. This property features a Ring Doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device (including devices linked to the camera such as the alarm system’s motion detector) or when the video doorbell button is pressed. This property also features 2 exterior security cameras: 1 camera is located on the front porch facing the porch and front yard/driveway, and 1 camera is on the back patio facing the patio and backyard. The cameras are outward facing and do not look into interior spaces

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

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

Walk to Balderdash Cellars | Newly Updated | Tanglewood Minutes Away | Mountain Views Breathtaking mornings begin at this house set against the peaceful backdrop of Richmond Pond and the surrounding mountains. You’ll find an ever-changing natural beauty as you enjoy fall foliage or a true winter wonderland. Whether you’re staying close to home to kayak on the pond, sipping through vineyards, or visiting Tanglewood, this Richmond vacation rental is a hidden gem in the heart of the Berkshires. -- THE PROPERTY -- C0583642490 OUTDOOR LIVING - Private 3 acres w/ fenced-in area - Furnished deck w/ seating & dining set - Private hot tub - Gas grill, fire pit - Mountain & lake views - 2 kayaks & bicycles INDOOR LIVING - Smart TVs - Wood-burning fireplace - Dining table - Washer/dryer KITCHEN  - Renovated w/ new appliances - Stove/oven, refrigerator, dishwasher - Microwave, toaster, blender - Drip coffee maker (starter coffee provided) - Dishware/flatware ACCESSIBILITY - Split-level home, stairs to access PARKING - Driveway (5 vehicles) - EV charger (WolfBox Level 2) -- THE LOCATION -- - Easy access to the best of the Berkshires, local wineries, restaurants, skiing & outdoor recreation - 0.2 miles to Balderdash Cellars & Richmond Pond Boat Ramp - 2 miles to Hancock Shaker Village - 5 miles to Bousquet Mountain Ski Area - 8 miles to Tanglewood Theater - 11 miles to Norman Rockwell Museum - 16 miles to Jiminy Peak Mountain Resort - 22 miles to Jacob's Pillow -- 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/ $100 fee (+ fees & taxes) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in SECURITY CAMERA INFORMATION - 1 exterior device - Location: front door - Coverage: entry Licence number: C0583642490

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

Get the cozy bed and breakfast feel all to yourself at this New Lebanon vacation rental. This sprawling home with 5 beds, 3 full baths, and 2 half baths at the base of the Berkshires still has all of the charm from its construction in 1790 and then some! With multiple sitting rooms and 33 private acres of lush landscape to explore, the whole crew will find relaxation at this beautiful retreat. Visit historic sites and museums, hit the ski slopes, or simply enjoy the views from the deck. -- THE PROPERTY -- Jetted Tub | On-Site Pond | 8 Mi to Ski Area | 3,600 Sq Ft Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Twin Bed | Bedroom 5: 2 Twin Beds | Loft: Full Sleeper Sofa INDOOR LIVING: Flat-screen TV, board games, fireplace, WFH workspace, dining table, en-suite bathroom OUTDOOR LIVING: Private acreage, deck, dining area KITCHEN: Cooking basics, dishware/flatware, dishwasher, refrigerator, stove, microwave, coffee maker, toaster GENERAL: Free WiFi, ceiling fans, central A/C, linens/towels, washer/dryer, laundry detergent, trash bags/paper towels FAQ: No A/C in old wing ACCESSIBILITY: Stairs required to access, 2-story home PARKING: Driveway (3 vehicles), street (first-come, first-served) -- THE LOCATION -- HISTORIC SITES: Hancock Shaker Village (4 miles), Berkshire Museum (9 miles), Herman Melville's Arrowhead (11 miles), The Mount, Edith Wharton's Home (15 miles), Norman Rockwell Museum (17 miles), Naumkeag (17 miles) LOCAL HIGHLIGHTS: Lebanon Valley Speedway (6 miles), Colonial Theatre (9 miles), Tanglewood (13 miles), Berkshire Botanical Garden (15 miles), Downtown Albany (30 miles) OUTDOOR ADVENTURES: Bousquet Mountain Ski Area (8 miles), Onota Lake Beach (10 miles), Jiminy Peak Mountain Resort (11 miles), October Mountain State Forest (16 miles) AIRPORT: Albany International Airport (37 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 2-story home requires using an exterior staircase to enter - NOTE: The property features central A/C in the new wing but not the old wing - NOTE: This property has a strict max occupancy of 10. Guest count is not to exceed 10 guests at any time

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 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

Welcome to Red Rock Summit, where an award-winning architect-designed home takes advantage of majestic views at every turn. This contemporary 4-bedroom, 4-bathroom home on 80 impressive acres is just 2.5-hrs from NYC & Boston. Enjoy the bright and airy interiors and abundant outdoor amenities, including a large pool, sauna, serene swimmable pond, and firepit. Explore nearby villages for shopping and dining, or hit the slopes at Catamount Ski Area. Welcome to a mountain retreat like no other. Situated in the peaceful Chatham, NY countryside, this contemporary home offers a perfect blend of modern living, natural beauty and tranquil surroundings. With around 4,400 square feet of living space on a generous 80-acres, it’s a testament to thoughtful design and the allure of the great outdoors, boasting a rich array of amenities, including a spacious swimming pool, a swimmable pond and awe-inspiring panoramic views that grace every room. The open plan design of the ground floor is highlighted by large glass sliding doors that line the front wall and allow abundant natural light and stunning outdoor vistas. A sense of elegance and simplicity permeates the decor, creating an atmosphere that is both clean and inviting. The living area is centered around a cozy fireplace and a flat-screen TV, creating a comfortable space for relaxation. The kitchen is a standout, featuring top-of-the-line appliances, a spacious island with marble countertops, wooden cabinetry, equipped with a Viking refrigerator, Miele stove and oven, Bosch dishwasher, microwave, toaster, blender, and a coffee machine. The adjacent dining area, with seating for eight opens onto the expansive wooden deck with alternative al fresco dining, fresh mountain breezes and breathtaking mountain views. Upstairs, you’ll discover four bedrooms. The master bedroom boasts a king-sized bed, along with an ensuite featuring a roomy walk-in shower and a separate, generously sized bathtub. The glass sliding doors offers breathtaking views of the picturesque mountains all around. Access to the deck is strictly off limits while we repair the decking. Bedrooms two and three have queen-sized beds, and the fourth bedroom has two twin beds. There are three guest bathrooms, one with a walk-in shower and double vanity sinks, another with a shower and bathtub combo, and a fourth bathroom with a walk-in shower on the ground floor. A versatile bonus room includes a work-friendly station, a comfortable reading nook, and a second TV for various activities. The outdoor spaces of this estate offer an array of amenities to savor, relax, and soak in the breathtaking vistas. From the private patio that open from the ground floor living spaces to the inviting swimming pool complete with sun loungers. Enjoy a scandi-experience in the newly added barrel sauna just steps from the back door, or jump in the serene swimmable pond and enjoy nights by the fire pit! Mature trees surround the property, enhancing the sense of seclusion and tranquility. Throughout the home, every room offers remarkable views, making the most of the picturesque surroundings. This property seamlessly combines contemporary style with the natural beauty of Chatham, offering a unique and harmonious lifestyle. Please note that the deck off the upstairs master bedroom is strictly off limits while we repair the wooden decking. Red Rock Summit is approximately 2.5 hours from New York City and Boston. You’ll definitely want a car to get enjoy the region. ᨒ Catamount Mountain: 16.6 mi In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. There is plenty of parking on the premises. *Please note that the pool is available during the summer season only. Please inquire regarding opening and closing dates. *The pool is not heated* *Learn more about the architect and home here: https://tmarch.com/austerlitz

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!

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 Sunny Pond by AvantStay! Escape to the enchanting retreat of Sunny Pond, a charming estate nestled on a private pond among the serene forest of the Berkshires. The inside of this estate boasts multiple living areas, allowing plenty of room to spread out. The main living area welcomes you with a fireplace and cozy ambiance, while the second living area features a casual atmosphere, making you feel right at home. These spaces invite you to kick back and spend quality time with your group. A third living area offers a more intimate setting, with a brick fireplace, rich brown interior decor, and plush leather seating. The spacious, gourmet kitchen is fit for a chef. A wrap-around island counter provides plenty of prep space, while a second island within features barstool seating for a quick snack. Fully equipped with top-of-the-line stainless steel appliances, including two dishwashers, two ovens, and two sinks, it’s ready for you to cook up a feast for your entire group. Head to the formal dining area, where a fireplace and chandelier set the scene for memorable gatherings. A second dining area, complimented by corner windows boasting views of the pond, offers a more casual setting for meals. The rest of the estate has a haven for every member of your group. A grand office allows you to work remotely while living lavishly. Head downstairs where a world of fun and entertainment awaits. A movie room boasts a spacious sectional and a large flat-screen TV for the ultimate movie marathon. Adjacent is the playroom, fully stocked with toys, books, and games. From a dollhouse to a dart board, a keyboard to a rocking horse, the playroom promises endless fun for kids of all ages. Fitness enthusiasts will find enjoyment in the gym, fully equipped with a wide variety of machines and exercise equipment, including a Peloton. After a long day, retreat to the comfort of your cozy bedrooms, where you can relax and recharge. The primary bedroom is designed with your comfort in mind, featuring a plush king bed, a TV for entertainment, a crib for little ones, and a sofa for added versatility. The second bedroom offers a comfortable queen bed, creating a peaceful space to unwind and rest. The full bathroom provides everything you need to refresh and rejuvenate, completing this welcoming retreat. For those seeking relaxation, the outdoors of Sunny Pond is the perfect escape. Retreat to one of the outdoor living spaces for your morning coffee or lounging with an afternoon book. Sprawling lawns and a playground offer plenty of room for activities. Go for a swim in the pond, head out on one of the provided pedal boats, or soak up the sun on the dock. You can even take a stroll out to the island in the middle of the pond, accessible by a bridge. It’s the perfect place for catch-and-release fishing! As the sun begins to set, gather around the fire pit to toast marshmallows and tell stories. Unwind from the day in one of seven comfortable bedrooms, each ensuring a restful night’s sleep. With ample amenities and plenty of space, Sunny Pond has been carefully curated for the perfect group getaway. This dream estate brings the perfect blend of fun and relaxation, promising a truly unforgettable stay in 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! 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. Home Truths: - This home allows one non-shedding dog with prior approval. Pets must be approved in advance and are subject to a $150 fee per pet. Bringing an unapproved pet into the home without AvantStay’s consent will result in a $500 fine per pet. - The pond is swimmable. Life vests, pond towels, pedal boats, rafts, and noodles are provided. - Catch and release fishing is allowed in the pond. Parking Details: - There is a 2-door garage and ample parking available in the long driveway. --- The room configuration is as follows: Primary Bedroom / King bed, crib Bedroom 2 / Queen bed Bedroom 3 / Queen bed, twin bed, twin trundle Bedroom 4 / Twin bed Bedroom 5 / Queen bed Bedroom 6 / Queen bed Bedroom 7 / 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.

Welcome to Chester! Fall head over heels in love with this gorgeous country home in the tranquil town of Austerlitz, NY. High vaulted ceilings, large view-facing windows, a fireplace, a formal dining area, and a chef-worthy kitchen are just a few of the many amenities that make this home a vacationer’s paradise. Outside, you can take in the fresh air from the large patio with breathtaking views as far as the eye can see. There’s plenty of comfortable seating and a dining table to accommodate dinner with your whole crew. When you’re ready, head to the Berkshires for more outdoor activities, views, hikes, museums, and art exhibits than you could ever hope to see in one visit. Book now! 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: - 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. - This home features a loft with a queen-sized bed. - The outdoor cushions seen in the photos are currently unavailable. - This home is located in the Berkshires, so you may encounter wildlife such as bugs and insects. - The driveway requires AWD or 4WD, as it can be steep and challenging to navigate. Guests should exercise caution, especially in adverse weather conditions. 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 w/ensuite Bedroom 2 / King bed Bedroom 3 / Queen bed Bedroom 4 / Two twin over twin bunk beds Loft / Full 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: n/a

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