Vacation Rentals By Owner In West Stockbridge, MA

Light-filled modern 4 bedroom, 3.5 bath home in the Berkshires. This lovely two story home features a master bedroom on each floor with its own private bathroom. Full kitchen, breakfast nook and separate dining room that seats 8. Screened porch perfect for dining and lounging. Wrap around covered deck to enjoy sunsets in the backyard. Tons of games and books, perfect for families. In the winter the easy-to-use gas fireplace will keep you warm and toasty - perfect for relaxing with a good book. Conveniently located to all that the Berkshires has to offer, like concerts at Tanglewood, antiquing, summer festivals, apple picking in the fall and skiing in the winter.

May and June rental available

West Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$514.16

Escape to Tranquility Glade, a newly renovated modern chalet set on 5.5 private forested acres in West Stockbridge, Massachusetts — just 6 minutes drive from Tanglewood and Kripalu. The charming towns of Lenox and Great Barrington are nearby.brBathed in natural light from skylights and cathedral ceilings, this home combines modern style, curated artwork, and designer furnishings with the calm of a private woodland retreat. The dramatic fieldstone fireplace anchors the open living space, creating a warm, inviting atmosphere year-round.brEnjoy your morning coffee on the spacious deck as sunlight filters through the trees. After a day exploring the Berkshires’ lakes, waterfalls, galleries, and trails, return to relax by the fire or gather under the stars at the outdoor firepit.brInside, you’ll find a sleek European kitchen, a king bedroom, two queen bedrooms, two full bathrooms, and a spacious lower-level den with a media area, workspace, and fitness equipment. The lower bathroom features a luxurious double walk-in shower — ideal after a hike or day on the slopes.brEvery detail is designed for comfort: high-speed WiFi, Air conditioning, a Weber grill, full laundry, toiletries, and all linens provided.brSecluded yet close to everything, Tranquility Glade offers the perfect balance of privacy, design, and location. Whether you’re here for a romantic weekend, a family getaway, or a peaceful work retreat in nature, you’ll arrive as guests and leave restored. brCome stay at Tranquility Glade — your private forest retreat where every morning feels like a fresh start and every evening wraps you in stillness.

Modern Designer Chalet on 5.5 Private Acres Near Tanglewood

West Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$537.51

Nestled on a quiet country road and minutes from the quaint village of West Stockbridge this fully renovated, modern, sunny farmhouse has two master suites, great outdoor space, and all that the Berkshires offers just minutes away. Eight minutes to Lenox and Tanglewood's Main gate, 18 minutes to Great Barrington and close to destinations North. Great restaurants, boutiques and bookstores abound.brFilled with farmhouse antiques, enjoy a beautiful and serene interior with hotel quality beds and bedding. Surrounded by beautiful plantings, two outdoor areas for reading, relaxing and dining. Kitchen deck includes a Weber grill and comfortable conversation area with bistro set. Two chaise lounges in the yard for soaking up the sun. Oversized garage and spare refrigerator just outside the well appointed kitchen. The home has easy keyless entry. Wi-fi and air-conditioned. 7 night minimum. No pets.

Rare Availablity-Beautiful Modern Farmhouse-Heart of the Berkshires

West Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$790.94

Welcome to Shaker Pine Cabin in the heart of charming West Stockbridge! Set on 4 peaceful acres, this newly renovated log cabin is tucked amongst private woods, yet a minute to all the amenities of the village. It is also just two miles to the famous Tanglewood, summer home of the Boston Symphony Orchestra, and Kripalu yoga center. Peruse quaint shops, explore entertainment at The Foundry, and grab a coffee at our local roastery No. 6 Depot. Minutes from trails, the Berkshires Botanical Gardens, and just a few miles from Butternut ski area. brbrThis modern log cabin is surrounded by towering trees with a quaint exterior porch and a surprisingly spacious open interior. Inside find stylish yet comfortable design mixed with rustic cabin appeal. brbrEnjoy cooking in the kitchen with all appliances, utensils, and bakeware you should need. Brew some delicious coffee with a French press, or enjoy the convenience of a Keurig maker. brbrAll rooms have split systems with A/C and heat to keep our guests comfortable every season and there are instructions in the cabin on how to easily use them. brbrUpon entering on the main floor, you'll find the living room with wood burning stove, a dining room with a table to seat 8, a well stocked kitchen, a bathroom with shower, washer & dryer, and one king bedroom.brbrUpstairs, you'll find the primary bedroom to the left with a king bed and a daybed perfect for a child. There's another full bathroom with a bathtub/shower and an additional guest bedroom with a third king size bed. brbrThe lower level is a great flex space where you can cozy up and watch movies on the large TV or enjoy games and bunk bed hangs. High chair and pack n' play in bunk room closet at your disposal for families with young children! brbrWi-fi throughout the house, and TVs in every bedroom, the living room, and lower level family room space. All streaming services are available. brbrFind fun activities and games in the lower level game corner: cards, clue, monopoly, sorry, twister, puzzles, etc. brbrWe are near tons of outdoor hiking, walking trails, waterholes, waterfalls, lakes, and fishing spots. Take advantage of the welcome binder, trail maps, and local magazines found in the cabin to inspire your adventures. brbrWe're excited to welcome guests who are mindful of caring for our home. With this in mind, we ask guests to kindly remove shoes indoors, lift furniture instead of dragging, and clean up any accidents promptly (we get it, they happen!) brbrAs hosts, we are always at your disposal to communicate about questions you may have. brbrThis is a non-smoking home and no pets or parties are permitted. Only the maximum number of guests is allowed- thank you for respecting our house rules and continuing to preserve the peaceful oasis it is! brbrWe hope to welcome you to Shaker Pine Cabin soon! Follow along on IG: @shakerpinecabin

Cabin

Shaker Pine Cabin: your cozy Berkshires retreat in the middle of it all!

West Stockbridge, Massachusetts, United States

Bed

Bath

9

Sleeps

$562.67

Katie's Cottage: Darling, Village-Center Living in West Stockbridge with Main floor Primary and Sun Room. Amenities include: 3 bedrooms, 2 full baths, (main floor primary) all stainless Appliances, Laundry on Main Floor. AC Throughout, Propane Fireplace, Sonos Sound System, Sun room, Brick patio with Outdoor Seating, Fire pit, and Propane Grill, Partially Fenced Private Yard. In-town, Close to Tanglewood and Ski Bousquet! No Smoking. Pets welcome with a fee.

Sunny West Stockbridge, Main floor Primary!

West Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$1490.91

Evergreen Home Vacation Rentals invites you to this sprawling 6-bedroom, 4.5-bathroom retreat featuring sweeping mountain views and an incredible indoor pool for year-round relaxation. This elevated estate is designed for groups, offering two living rooms, a sauna, a game area, and a sleek renovated kitchen.brbrEnjoy outdoor dining on the deck and peaceful privacy on a wooded lot. Whether lounging by the pool or exploring the hills, this is the ultimate modern Berkshire experience.brbrIf you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.brbrThe home is set off a private road, up a private driveway. There are no immediate neighbors in view from the property.brbrGuests will have access to the entire home, and property.brbrIdeal for groups, this sophisticated Berkshire retreat offers abundant indoor and outdoor spaces for relaxation and connection. brbrOn the main level, discover the impressive indoor pool, complete with doors leading to a screened porch and a spacious deck for seamless indoor–outdoor enjoyment. Adjacent to the pool, you’ll find a relaxing sauna and a full bath with shower—perfect for unwinding after a swim. Convenient poolside access to the kitchen makes entertaining effortless.brThe kitchen is thoughtfully designed for preparing large meals, featuring a gas stove, drip coffee maker, and a charming breakfast nook. A pass-through window opens to the dining room, keeping the space light, airy, and connected, while refreshed countertops and custom cabinetry offer timeless style and functionality.brA formal living room with a fireplace invites guests to gather or step out onto the expansive deck for outdoor dining or quiet moments in the Adirondack chairs overlooking the view. A cozy den provides a comfortable spot for movie nights, while the casual game room—complete with keyboard and ping pong table—sets the scene for lively fun. A convenient half bath completes this level of the home.brbrThe second floor hosts a serene primary suite complete with a private balcony, King bed, dressing room, and a spacious en suite bath featuring a tub and shower combination. A second guest bedroom offers a comfortable Queen bed and access to a nearby full bath, also with a walk in shower.brbrBeyond the convenient second-floor laundry area lies a generous guest room with a Queen bed, seating area, and writing desk—an ideal retreat for relaxation or remote work. Connected to this space is a cozy bedroom with a Twin bed, perfect for a child or guest who may need to be nearby overnight. The adjoining door can be closed for privacy when desired.brA sunken den on this level provides a relaxed lounge area, complete with bean bag chairs, games, and a quiet reading nook. A full bath serves this space, offering another tub/shower combination. Off this wing, an additional bedroom features two queen beds, ideal for families or groups traveling together.brbrAscending the spiral staircase from the second-floor den leads to the home’s upper level, where a charming third-floor bedroom awaits—featuring four twin beds and a welcoming, loft-style ambiance.brbrThoughtful sleeping arrangements ensure comfort for all guests, while the expansive private lot offers unparalleled seclusion. With contemporary design, curated spaces, and exceptional amenities, this home delivers a truly unforgettable Berkshire escape.brbrYou can walk in the neighborhood, but will need a car to get around the Berkshires effectively.brbr⭐️ LOCATION: The home is set off a private road and accessed via a private driveway, with no immediate neighbors in view, offering a truly secluded setting. Conveniently located just 4 minutes to downtown West Stockbridge, 6 minutes to Tanglewood, 9 minutes to downtown Lenox, and 19 minutes to downtown Great Barrington.brbr⭐️ SKI ACCESS:br• 13 minutes to Bosquet Mountainbr• 24 minutes to Butternutbr• 30 minutes to Catamount and Otis Ridgebr• 32 minutes to Jiminy Peakbrbr⭐️ PETS: No pets permitted.brbr⭐️ PARKING: Off-street parking available. 4WD is strongly recommended during winter months.brbr⭐️ POOL HEAT: Pool heating is available for an additional $150 per night. Guests may also choose to use the pool without heat. Please select the optional pool heat charge at booking and notify us in advance so the pool is ready upon arrival.brbr⭐️ POOL SAFETY: The pool may be accessed from two interior entry points—one near the kitchen and one adjacent to the sauna and bathroom—as well as from the screened-in porch. The pool is equipped with a heavy-duty electric safety cover designed to support weight in the event of a fall. The switch is locked for safety. Please ensure the pool is covered and the switch locked when not in use. Children must be supervised at all times.brbr⭐️ SAUNA: The sauna’s electric heater is available for guest use. The wood stove inside the sauna is not available and remains locked for safety.brbr⭐️ FIREPLACES: The living room fireplace is available for guest use. Fireplaces in the primary bedroom and den are not available.brbr⭐️ DAMAGE PROTECTION: Your reservation includes a $20 accidental damage insurance fee, allowing you to relax and enjoy your stay with peace of mind. If any damage occurs, please notify us so we can arrange timely replacements for the next guest.

Expansive Mountainside Escape by Evergreen Home

West Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$280.37

Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and scenic atmosphere in the area, and soak in the culture. brbrMinutes away from Tanglewood Music Center, Kripalu and near Lenox, Great Barrington, the Norman Rockwell Museum, and Jacob's Pillow.brbrLess than 5 minutes away from Stockbridge Bowl / Lake Mahkeenac's boat launch ramp for all you fishers and kayakers out there! brbr**If the weekend you want is unavailable, please email us to see if our other unit is available!**brbrMattresses were replaced in June 2021

Condo

Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)

West Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$229.02

Escape to the Garden House in picturesque Stockbridge. Fifteen minutes to three ski areas. Fully furnished and equipped home with three bedrooms featuring a king bed, queen bed, and a sofa bed, plenty of space to relax. Enjoy a tranquil atmosphere where you can unwind after a day of skiing. Walk to Tanglewood and the Stockbridge Bowl. The community gym features an indoor heated pool and gym. There are tennis courts and beautifully landscaped open areas. Whether you’re curling up indoors or stepping out, this marvelous home offers a tremendous retreat with it's extraordinary location near restaurants, theaters, museums, and more in Lenox, Stockbridge, and Great Barrington. There is a minimum of one month reservation required, and discounts are available for longer stays.

Condo

Lots of snow! Ski, snowshoe/ heated pool - fabulous in beautiful Stockbridge

West Stockbridge, Massachusetts, United States

3

Bed

Bath

Sleeps

$779.7

Summary:brbrCrossbridge 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)brbrbrbrThe Space:brbrThis 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. brbrbrbrMain House: brbrbrbrWith 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.brbrbrbr 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. brbrbrbrThere 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. brbrbrbrThe 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.brbrbrbrSurrounded 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.brbrbrbrGuest Access:brbrPlease Note:brbrThere 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.brbrbrbrGuests do not have access to the garage.brbrGuests have access to a row boat however, swimming or fishing in the pond is prohibited due to the wildlife.brbrGuests do not have access to the piano. It is locked as it is very fragile.brbrbrbrThe Neighborhood:brbrWest Stockbridge, Massachusetts is known for its quaint charm, rich history, natural beauty and year round appeal. Whether you're an outdoor enthusiast, an art lover or a foodie, this destination has something for everyone.brbrbrbrFor winter thrills, hit the slopes at nearby Bousquet Mountain or Ski Butternut both offering trails for skiers and snowboarders of all skill levels. In the warmer months, explore the town's numerous hiking trails including the scenic routes at Monument Mountain and Ice Glen where you’ll find picturesque views and diverse terrain. The Williams River is perfect for kayaking and canoeing allowing you to immerse yourself in the area's natural beauty. Don't miss TurnPark Art Space, an open-air museum set in a former quarry featuring sculptures, exhibitions and performances in a beautiful outdoor setting.brbrbrbrWhen it's time to refuel, enjoy a meal at Amici, a cozy Italian spot offering pasta, pizza and classic Italian dishes or head to Truc Orient Express, a hidden gem serving up authentic Vietnamese pho and other flavourful dishes. Try Number Six Depot a beloved coffee shop and roastery in the oldest train station in the Berkshires. For a more upscale experience, Once Upon a Table in Stockbridge focuses on fresh, seasonal ingredients in a refined setting. If you're venturing south, Prairie Whale in Great Barrington offers farm-to-table American fare in a charming house with a hip, rustic feel.brbrbrbrWith a mix of outdoor adventures, vibrant art, interesting heritage and great food, there’s no shortage of things to do in the Berkshires. Explore nature or dive into the region's cultural offerings, there's something for everyone!brbrbrbrGetting Around:brbrCrossbridge 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.brbrbrbrOther Things to Note:brbrThe 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.

Crossbridge: Vintage Charm + Unique Character

West Stockbridge, Massachusetts, United States

Bed

5

Bath

7

Sleeps

$1181.03

Evergreen Home Vacation Rentals invites you to this refined log cabin featuring a heated saltwater pool, hot tub, and mountain views. Just 15 minutes to Butternut, this 3-bedroom (5 bed), 3.5-bath escape boasts a stone fireplace, screened porch, and spacious suites.brbrOutside, enjoy the fire pit, lush gardens, and pool house. Perfectly located near West Stockbridge, Lenox, and Great Barrington, this retreat offers rustic charm with modern luxury. Your private Berkshire getaway awaits!brbrbrIf you have any questions please message via your booking platform. Our goal is always for our guests to enjoy a relaxing stay at a beautiful home.brbrThis is a quiet neighborhood road. The home is private, and set back far from the road at the top of a hill. brbrGuests will have access to the entire home, and property.brbrWelcome to your perfect Berkshires getaway! Just a short trip from New York or Boston, this 3-bedroom, 3.5-bath home combines rustic log cabin charm with the open, airy spaces of modern living.brbrInside, the first floor features a dramatic great room with a stone fireplace, an open kitchen and dining area with cherry floors and custom pine cabinetry, plus a giant screened porch for relaxing outdoors in any weather. The main-level bedroom suite includes private porch access, a spacious bathroom with soaking tub and shower, walk-through closet, and convenient first-floor laundry. Upstairs, you’ll find two additional bedrooms—each with its own full bath—plus, a versatile office space that doubles as a cozy guest room with an additional bed. Guests 16 and older can enjoy the fully equipped home gym located in the lower level, featuring a Soul Cycle bike, weight bench, punching bag, and more.brbrStep outside and enjoy the beautifully landscaped grounds that flow naturally into the surrounding woods, with unique views of the Berkshire Hills. The heated saltwater pool is perfect for summer days, complete with a hot tub and pool house/cabana. Please note the hot tub is integrated into the pool, and open seasonally. Unwind by the dramatic stone fire pit, stroll through the beautifully landscaped garden beds, or enjoy a relaxing moment on the swing set—all thoughtfully designed to enhance your Berkshires retreat. brbrAll of this is just minutes from downtown West Stockbridge, and less than 15 minutes to Tanglewood, Lenox, Great Barrington and Stockbridge—putting the very best of the Berkshires at your doorstep.brbrYou will need a car to get around the Berkshires efficiently. You will need AWD/4WD in the winter to ascend the driveway.brbr⭐️ LOCATION: The home is set back on a quiet neighborhood road, providing a private and peaceful setting.brbr⭐️ POOL: Open seasonally from May through October, with exact dates determined by weather conditions.br• June 1 through Labor Day: Heated to 82°F at no additional cost. Guests may request a higher temperature for an additional fee—please contact us in advance.br• May & after Labor Day: Pool heating may be available for $175 per day, but is not guaranteed. Advance notice is required to ensure the pool is ready.br• Heating above 82°F during June–Labor Day is available for an additional fee—please inquire in advance.brbr⭐️ HOT TUB: Integrated with the pool and available only when the pool is open seasonally.brbr⭐️ POOL HOUSE: Open seasonally. Not suitable for additional sleeping arrangements.brbr⭐️ WINTER DRIVING: AWD/4WD required to navigate the driveway during winter months.brbr⭐️ SKI ACCESS:br• 15 minutes to Ski Butternut & Bousquet Mountainbr• 20 minutes to Otis Ridgebr• 30 minutes to Catamount & Jiminy Peakbrbr⭐️ SWING: A tree-mounted swing is available on the property (separate from the swing set). Capable of going very high. Use with caution—guests 16+ only.brbr⭐️ GYM: Gym facilities are available for guest use. Guests must be 16+. The bike is a SoulCycle requiring an Equinox virtual membership to log in.brbr⭐️ PETS: One small, trained, hypoallergenic dog may be allowed on a case-by-case basis with prior approval. Pets must be under 50 lbs, fully housebroken/trained, and no multiples. $150 pet fee applies if approved.brbr⭐️ PARKING: Free on-site parking for up to 6 vehicles.brbr⭐️ DAMAGE PROTECTION: Your reservation includes a $20 accidental damage insurance fee, allowing you to relax and enjoy your stay with peace of mind. If any damage occurs, please notify us so we can arrange timely replacements for the next guest.

Modern Log Cabin with Saltwater Pool & Mountain Views By Evergreen Home

West Stockbridge, Massachusetts, United States

Bed

Bath

9

Sleeps

$1094.8

Summary:brbrCrossbridge 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.brbrbrbrNearby towns: Stockbridge(10mins), Lee(15mins), Great Barrington(20mins), Catamount Ski Mountain(25mins)brbrbrbrThe Space:brbrThis 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. brbrbrbrMain House:brbrbrbrWith 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. brbrbrbrIn 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.brbrbrbrThere 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.brbrbrbrThe 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.brbrbrbrThe Apartment:brbrbrbrThis 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.brbrbrbrThe 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.brbrbrbrThis 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.brbrbrbrSurrounded 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.brbrbrbrGuest Access:brbrGuests do not have access to the garage.brbrGuests have access to a row boat however, swimming or fishing in the pond is prohibited due to the wildlife.brbrGuests do not have access to the piano. It is locked as it is very fragile.brbrbrbrThe Neighborhood:brbrWest Stockbridge, Massachusetts is known for its quaint charm, rich history, natural beauty and year round appeal. Whether you're an outdoor enthusiast, an art lover or a foodie, this destination has something for everyone.brbrbrbrFor winter thrills, hit the slopes at nearby Bousquet Mountain or Ski Butternut both offering trails for skiers and snowboarders of all skill levels. In the warmer months, explore the town's numerous hiking trails including the scenic routes at Monument Mountain and Ice Glen where you’ll find picturesque views and diverse terrain. The Williams River is perfect for kayaking and canoeing allowing you to immerse yourself in the area's natural beauty. Don't miss TurnPark Art Space, an open-air museum set in a former quarry featuring sculptures, exhibitions and performances in a beautiful outdoor setting.brbrbrbrWhen it's time to refuel, enjoy a meal at Amici, a cozy Italian spot offering pasta, pizza and classic Italian dishes or head to Truc Orient Express, a hidden gem serving up authentic Vietnamese pho and other flavourful dishes. Try Number Six Depot a beloved coffee shop and roastery in the oldest train station in the Berkshires. For a more upscale experience, Once Upon a Table in Stockbridge focuses on fresh, seasonal ingredients in a refined setting. If you're venturing south, Prairie Whale in Great Barrington offers farm-to-table American fare in a charming house with a hip, rustic feel.brbrbrbrWith a mix of outdoor adventures, vibrant art, interesting heritage and great food, there’s no shortage of things to do in the Berkshires. Explore nature or dive into the region's cultural offerings, there's something for everyone!brbrbrbrGetting Around:brbrCrossbridge 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.brbrbrbrOther Things to Note:brbrThe 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.

Crossbridge: Vintage Charm + Unique Character.

West Stockbridge, Massachusetts, United States

Bed

7

Bath

11

Sleeps

$572.01

Berkshire Farm House rental combining the charm of an original 18 Berkshire with modern conveniences and luxury amenities situated on 47 magnificent acres in the Alford Valley. There is a beautiful original barn, separate cottage for on-site caretaker, gardens and apple orchard. The surrounding woods have wonderful walking paths and views are truly spectacular. Ideal for biking & hiking. Great Barrington, Lenox and Tanglewood are each less than a 15 minute drive.

Country House

18 Century farmhouse with modern conveniences set on 47 magnificent acres

West Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$410.08

Welcome to our idyllic farmhouse in the beautiful Berkshires, where you’ll enjoy the tranquility and comfort of country living any season of the year. Relax, slow down, watch the birds in the garden, listen to the babbling brook. Or take advantage of all the Berkshires has to offer – cultural attractions, fine dining, outdoor adventures, shopping and more. Spend some time here and create memories for years to come.brThis is a 2 story 1840's farmhouse in the Berkshires with original ceiling beams and 16' floor boards in much of the house.brFully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains.brbrIt has a fully equipped country kitchen with dish washer, microwave, toaster oven, coffee maker, and lots of cooking utensils.brbrA full dining room with butcher block table that seats 12 and 2 complete sets of dinnerware; glasses, mugs, and wine glasses.brbrA large living room with 2 full couches (one is a comfortable queen pull out and the other is a great napping or over night sleeping couch), a love seat, and rocking chairs. WiFi/Cable TV/VCR/DVD/Stereo/and CD player.brbr1 bedrooms upstairs with queen bed, 2 with double beds, and 1 with single bed.brbr1 bedroom downstairs with king bed.brbrAll beds have memory foam toppers, all linens included.br1 COMFORTABLE (really) queen pull out couch in living roombrbrDownstairs bathroom has washer and dryer with soap; shower has soap and towels.brbrPerennial gardens and large vegetable garden.brbr2 miles from downtown West Stockbridge where you can shop and dine; 2 minutes from Card Lake Pond for swimming and fishing; 15-20 minutes to ski areas; 10 minutes from Tanglewood, theatres and movies; 10 minutes from Norman Rockwell Museum; 20 minutes to Pittsfield; 2.25 hours from Boston; 2.5 hours from NYC.brbrWooded and river walks/bicycling, cross country skiing/snowshoeing right out the door.brbr

Country House

Vacation in a Berkshire Farmhouse

West Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$555.17

Get away to this peaceful Berkshire escape tucked into the woods of Pixley Hill in West Stockbridge! The home boasts 3 full bedrooms as well as a smaller kids room and two extra special twin beds in a fun lofted space that feels like a campout even for the biggest of kids. Enjoy a night tucked in by the fireplace or a lazy Sunday lounging in the tub connected to the master bedroom. If being nestled away in the woods but still only 15 minutes to Tanglewood is your thing, hurry up and book today!brbr✔ High-speed Wi-Fibr✔ Smart TVbr✔ Fully equipped kitchenbr✔ Washer & dryerbr✔ Free parkingbr✔ Wood fireplacebr✔ Pellet stovebr✔ Sunroombr✔ Pet-friendlybr✔ Pack n Play Travel Crib (Upon request)brbr➥ 7 mins to Chesterwoodbr➥ 10 mins to Berkshire Botanical Gardenbr➥ 10 mins to Norman Rockwell Museumbr➥ 11 mins to Olivia`s Overlook at Yokun Ridge Reservebr➥ 12 mins to The Lion`s Denbr➥ 13 mins to The Mahaiwebr➥ 14 mins to The Berkshire Theatrebr➥ 14 mins to Tanglewoodbr➥ 15 mins to Stockbridge Bowlbr➥ 15 mins to Ski Butternutbr➥ 15 mins to W.E.B. Du Bois National Historic Sitebr➥ 16 mins to Lenox Mountainbrbr✦BEDS & BATHS✦brInside we have 4 bedrooms and 2 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience.brbrRoom Breakdown:brMain Bedroom - 1 Queen bedbrBedroom 2 - 1 Queen bedbrBedroom 3 - 1 Queen bedbrBedroom 4: 3 Twin bedsbrbrAll Berkshire Vacation Rental Co.™ Properties include:br - Support from full-time local team available daily from 9am to 9pmbr - Professional housekeeping & property inspection prior to guest arrivalbr - Towels, linens, and bath productsbr - At least a mornings worth of coffee to get you startedbr - Learn more @berkshirevacationrentalbrbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbr• DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized.brbrCleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property.brbrTo provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area.brbrThere is space for parking multiple cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.brAs hosts, we generally like to abide by the golden rule. Treat our space well, and we`ll treat you well in return. brno smokingbrno overnight guests beyond those outlined in the bookingbrno partiesbrplease respect all quiet hoursbrPlease see guest packet for more information.

Pixley Forest | 15 Mins To Tanglewood • Fireplace

West Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$541.6

This secluded mountaintop property sits on 10 acres in the very heart of the Berkshires. You will be a 3 minute drive to the village of West Stockbridge, 10 minutes from the world famous Tanglewood, and just 20 minutes from Jimmy Peak, the largest and nicest ski resort in Massachussets.brbrThe house occupies 3,500 square feet over 3 floors, with 4 bedrooms and 3.5 baths. The common spaces and bedrooms are all well proportioned and relaxed, offering an experience of privacy and exclusivity that can only be provided by a property such as this.brbrThe house is approximately 120 miles from New York City, a roughly 2.5 hr drive over the Taconic Parkway's rolling hills and beautiful vistas. The house is perched at the top of a hill that is reached via a 1/4 mile private driveway that winds uphill through a protected bird sanctuary. brbrThe ground floor has a oversized living room with wood burning fireplace, a formal dining area, a newly built kitchen. The primary bedroom suite is conveniently located on the same level.brbrThe second floor has two spacious bedrooms and two en-suite bathrooms. Both bedrooms feature queen sized beds, and one has a working wood fireplace.brbrThe finished basement level features a large kids room with a bunk bed that sleeps 2. The room has a large screen TV, video games, and a lot of books. The basement also features a laundry room.brbrAt the front of the house there is a large deck with comfortable seating, a barbecue, and westerly views that provide for spectacular sunsets.brbrThe back of the house has a screened patio with dining table and chairs. This is a very quiet and cozy space, perfect for drinking your morning coffee.

Canary Lodge - Berkshires Mountaintop Retreat - 8 Guests

West Stockbridge, Massachusetts, United States

Bed

3

Bath

8

Sleeps

$211.57

Keep it simple at this peaceful and centrally-located apartment set on 17 private acres. Bright, clean and serene; you won't want to leave. Close to all of the Berkshires main attractions, this one bedroom loft is spacious and comfortable and offers a classic old school rental feel.brbr***Please note: we rented our apartment to Tanglewood and Boston University Tanglewood Institution for many years, hence the lack of reviews.***

Apartment

Experienced Hosts. Quiet, Romantic, Spacious Apartment, Pet Friendly.

West Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$345.56

Need a break from city life Escape to our enchanting private cabin nestled in the woods, where romance and seclusion await. This charming retreat offers an intimate setting surrounded by nature, perfect for unwinding. Enjoy cozy evenings by the wood burning stove and serene mornings on the deck, all while being just a few minutes' drive from all the Lenox/Stockbridge attractions, including Tanglewood, museums, cafes, restaurants and hiking/ski trails. Experience the perfect blend of tranquility and convenience in your own woodland haven. brbrEnjoy quiet mountain serenity, minutes from all Berkshires attractions! brbrThis is a freshly renovated mountain cabin, set on 14 acres of private land at the end of a dead end mountain road. Located on picturesque mountain road in West Stockbridge this home is a short drive from Tanglewood (5 mins), Kripalu (5 mins), Wineries (15 mins), Museums (10 mins), Skiing (20 mins), Hiking (2 mins), Theatre, Shopping and Dining. brbrThis is a perfect location for a romantic getaway or simply a place to come recharge!brbrThe cabin itself sits on 2-3 acres of a larger private estate. There is plenty of lovely green space for walks or pure relaxation in nature.

Cabin

Serene rustic cabin in the Berkshires!

West Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$376.97

Enjoy your stay in heart of the Berkshires! This 3 bedroom, 2 bath ranch vacation house in set on 17 private acres. Enjoy the sounds of nature while sitting on the private back deck sipping on coffee or enjoying a fire in the fire pit. This property is within walking distance to the Williams River - a perfect area to go swimming, fishing or a stroll. brbrbrWe have rented our home for many years to private institutions hence the lack of reviews :)

Experienced Hosts, 10 min to Tanglewood, Quaint Berkshires Getaway

West Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$277.71

Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This 2BR home can sleep up to 6 people. All of our mattresses have been replaced in June '21.brbrEnjoy a nice cup of hot chocolate by the fireplace in the living room after a day of exploring the town. brbr★ LOCATION ★brWe're conveniently located in the middle of these major attractions: brbr• Kripalu Center For Yoga & Health (4 minutes away)br• Tanglewood (5 minutes away)br• Stockbridge Bowl - has a cute beach and boat launch ramp (3 minutes drive, 10 minutes walk)br• Norman Rockwell Museum (7 minutes away)br• Butternut - great for skiing (20 minutes away)br• Jacob's Pillow (30 minutes away)brbr★ GUESTS ★brOur cute and convenient condo is perfect for:br• couples on a romantic getawaybr• families on a ski tripbr• friends on a long overdue trip to reconnectbr• performing artists from Tanglewoodbr• those looking for longterm or temporary housingbrAll are welcome!brbr★ ABOUT ★brbrCONDObr• Ground floor (no stairs) br• 1 Floor br• 2 Bedroombr• 1 Bathroombr• Large yard br• ParkingbrbrLIVING ROOMbr• Gas fireplacebr• Sofa bed br• TVbrbrKITCHEN br• Dishwasher br• Washer and dryer (perfect after a day of hiking or skiing!) br• Utensils, plates, pots, pans, etc. - everything you need to have a nice home cooked meal brbrDINING ROOMbr• Dining table - seats 4brbrBEDROOMbr• Queen bedbr• Side tablebrbrBATHROOMbr• Hair dryerbrbrOUTDOORSbr• Guests are welcome to bring their own BBQ grill and outdoor seating to be enjoyed in the large outdoor spacebrbr★ PETS POLICY ★ brPets allowed (weight and breed restrictions may apply). There is a $150 non-refundable pet fee.brbr★ COVID-19 SANITIZATION ★brHeath, safety, and wellbeing of our guests are of the utmost importance. For this reason, we use a thorough cleaning process after each check-out.brbrbrIf the weekend you want is unavailable, email us to see if our unit next door is!br

Condo

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)

West Stockbridge, Massachusetts, United States

Bed

Bath