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Crossbridge - Vintage Charm & Unique Character

House in West Stockbridge, MA

11 guests·6 bedrooms·7 bathrooms
5.0 · 11 reviews

Why you'll love this stay

Outdoor Living

Outdoor Living

Private 25-acre grounds with pond and tranquil woodland views.

Location & Accessibility

Location & Accessibility

Ideal base for Berkshire explorations with nearby towns and venues.

Group & Family Friendly

Group & Family Friendly

Spacious gathering spaces and multiple en-suite retreats for everyone.

Property details

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, large windows & multiple laptop friendly work spaces. Nearby towns: Stockbridge(10mins), Lee(15mins), Great Barrington(20mins), Catamount Ski Mountain(25mins) Pets: Not allowed. Smoking: Not allowed. Events: Not allowed. Not suitable for children or infants. Reason: The property is not child friendly.. Additional rules: AGE REQUIREMENT Primary guest booking must be 25 years or older. PETS Sorry, pets are not permitted at this property. SMOKING No smoking is permitted inside the house. If you must smoke, please do so outside and dispose of butts properly.. EXCESSIVE CLEANING FEES We kindly ask that guests treat the home with care and respect. Should the property require cleaning beyond the standard turnover—due to excessive mess or incidents involving bodily fluids such as blood, vomit, or waste—a $500 fee may apply. Any linens or furnishings damaged beyond repair will also be subject to replacement charges. These situations are considered outside the scope of routine housekeeping and require specialized attention to ensure the safety and well-being of our team. MID-STAY CLEANING REQUIREMENT For stays of 28 nights or longer, a guest-paid mid-stay cleaning is required. The cleaning will be scheduled at a mutually convenient time during your stay. The cost varies by property and will be confirmed before scheduling. ACCURATE GUEST COUNT The number of guests must be accurately disclosed at the time of booking. While we don’t charge extra for additional guests up to the home’s maximum occupancy, this information is essential so we can properly prepare and stock the home. Please note that penalties may apply if guest counts are inaccurate or intentionally misrepresented. OUTSIDE SERVICE PROVIDERS Outside staff such as private chefs, massage therapists, or other service providers are welcome, but prior approval is required before they come on-site. SUPPLEMENTAL AGREEMENTS Guests may be required to sign a rental agreement. If applicable, it will be sent after the booking is confirmed. SEPTIC Please be mindful of the septic system and do not flush anything down the toilets or drains other than toilet paper. This includes any and all personal hygiene products, baby wipes, bleaches and strong chemical cleaners. Please note the FIREPLACE is temporarily out of service and should not be used during your stay. We apologise for the inconvenience and appreciate your understanding. 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, a 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. West 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. For 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. When 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. With 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! 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 Please note the FIREPLACE is temporarily out of service and should not be used during your stay. We apologise for the inconvenience and appreciate your understanding.

Sleeping arrangements

Bedroom 1

1 King Bed

Bedroom 2

1 Single Bed

Bedroom 3

1 King Bed

Bedroom 4

1 Queen Bed

Bedroom 5

1 King Bed

Bedroom 6

1 Queen Bed

What’s included

  • Parking

    Parking

  • Washer

    Washer

  • Dryer

    Dryer

  • Air conditioning

    Air conditioning

  • Heating

    Heating

  • Kitchen

    Kitchen

  • Wi-Fi

    Wi-Fi

  • Balcony

    Balcony

Guest reviews

Star icon 5.0 | 11 reviews
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Shaun

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October 2026

Beautiful place! Very spacious and clean. And such charm.

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Fiorella

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October 2026

We loved our stay here - the property is spacious the foliage views were perfect

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Robbie

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July 2026

The house+apartment was extremely well equipped. Lots of toys for the kids. Both kitchens had LOTS of cooking equipment, dishes, silverware, etc. We ate in for four days with no problem. Baking projects were undertaken. Additional relatives came for dinner.The linens were cotton (NOT microfiber, awful to sleep on). The ac kept us comfortable inside. And there was space galore, more than enough for grandparents, the next generation, a spouse, a nanny, and three kiddos under 5. There were two [small] downsides: first, renting both parts of the house was expensive. We would have hoped for some discount for having rented both parts. The second downside: this property is far away -- at least 30 mins by car -- from the towns of the Berkshires. If isolation is what you want, with civilization possible (Mass MOCA, Tanglewood, touring musical theatre, etc), and if you are somewhat price insensitive, then this house+apartment is a wonderful choice for a crowd.

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Tara

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July 2026

Red Cottage was a little slice of heaven. Perfect for groups or families...there is so much space to enjoy. The landscape is beyond fantastic. My only regret is not staying for longer.

Know before you go

House rules

Check-in: 4:00pm

Checkout: 11:00am

No pets allowed

Min. age to rent: 25

No smoking

No parties

Have a question about this property?

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