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Crossbridge Main House - Vintage Charm & Unique Character

4 bedrooms · 4 beds · 5 bathrooms · Sleeps 7
House

Where you’ll sleep

King
Bedroom 1: Master
Twin
Bedroom 2
King
Bedroom 3
Queen
Bedroom 4

A spacious 25-acre estate blending vintage New England charm with unique character, perfect for a peaceful retreat.

  • –Expansive 25-acre private estate with pond, gazebo, and walking trails.
  • –Historic home blending vintage New England charm with unique turreted architecture.
  • –Gourmet kitchen featuring a distinctive stone brick wall pizza oven.

Crossbridge is a spacious 4 bed, 5 bath property 2. 5 hrs from Boston & under 3 hrs from NYC.

About this property

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.

The area

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!

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.

Notes from your host

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. It’s scheduled for an inspection in early November. We apologise for the inconvenience and appreciate your understanding.

full description, the area, host notes


Managed by Red Cottage

Red Cottage

New York, NY

4.8★

3,492 reviews

Red Cottage is a vacation rental management company offering curated Catskills, Hudson Valley, Berkshires and Northeast properties with guest services and multi-platform listings.


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Guest Reviews

5.0★ · 6 reviews
★★★★★

“The home was very special; lots of different spaces to explore and settle into for reading, talking and relaxing. Layout of the house is very open and the surrounding gardens were so lovely. Every room had a wonderful view of the grounds. Great kitchen that was well stocked with cookware, spices and multiple ways to make coffee/tea. Overall, a wonderful visit - we would definitely stay there again on our next trip to the Berkshires.”

Guest · Sep 2026

★★★★★

“Incredible house. One of the cooler stays I’ve had on Airbnb. Went here for a family getaway. Spacious, clean, beautiful. We used the pizza oven which was a fun activity. Stellar place and management. 5 stars.”

Guest · Sep 2026

★★★★★

“Spectacular place for our family reunion in the Berkshires! So spacious and beautifully furnished, with windows for light to enter at every point during the day and outdoor seating in multiple locations (patios, front porch). We loved browsing the bookshelves and found the exercise cabinet (yoga mats and rollers) on the last day. Best Air BnB kitchen ever! Plenty of working space, with everything carefully labeled so there was no searching! And the host provided everything - spices, baking pans (with parchment paper), a range of pots and pans, great outdoor grill. Easy drive into nearby towns -- West Stockbridge, Stockbridge, Lenox, Great Barrington, even Williamstown -- so we were able to enjoy theater (Berkshire Theatre Group), museums (Clark Art Institute, Norman Rockwell Museum, Edith Wharton's home The Mount) and -- if we'd had more time -- Tanglewood is just down the road. We mostly cooked at home, but there are many great restaurants nearby. We would love to return!”

David · Sep 2025

Guests mention

well-stocked kitchen

Good for

Remote work


Rules & Policies


Location

West Stockbridge, Massachusetts

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