Hilltop Haven

Welcome to your private Hillsdale escape — an eclectic country retreat set on 19 secluded acres near the New York–Massachusetts border.

Throughout the home, modern design meets collected antique finds, creating rooms that feel stylish, comfortable, and full of personality. With three bedrooms, 2.5 bathrooms, and several distinct living areas, there is plenty of room for up to 10 guests to gather together or spread out.

The light-filled sunroom is the heart of the home. Surrounded by expansive windows and soaring ceilings, it offers a peaceful place to read, relax, or cozy up beside the wood stove after a day of skiing. Elsewhere, the book-lined library, colorful upstairs lounge, and quiet reading nook offer even more space to slow down.

In summer, spend your days beside the private seasonal heated saltwater pool, grill and dine outdoors, or gather around the fire pit overlooking Catamount Mountain. When temperatures cool, head to nearby Catamount for skiing and snowboarding, then return home to store your gear in the spacious mudroom and enjoy pool, ping pong, or a movie in the basement game room.

The fully equipped kitchen makes shared meals easy, while three thoughtfully arranged bedrooms provide comfortable accommodations for families and groups. The first-floor king suite offers added privacy and an en-suite bathroom. Upstairs, one bedroom has two queen beds, while another includes a king bed and two twins.

This is boutique hospitality with heart — professionally managed and thoughtfully prepared so you can focus on relaxing, reconnecting, and enjoying your stay.

OUTDOOR LIVING AT ITS BEST

• Private seasonal heated saltwater pool, typically open Memorial Day through September
• Fenced pool area with loungers
• Fire pit overlooking Catamount Mountain
• Propane grill and outdoor dining space
• Secluded setting surrounded by 19 wooded acres
• Expansive lawns and peaceful country views
• Complete privacy with no owner or other guests onsite

INSIDE, ENJOY

• Soaring, window-filled sunroom with working wood stove
• Eclectic mix of modern design and antique finds
• Fully equipped kitchen for shared meals
• Book-lined library with a decorative, non-operating fireplace
• Basement game room with pool table and ping pong
• TV lounge for movie nights
• Spacious mudroom for skis, boots, and winter gear
• Upstairs lounge and reading nook with daybed
• Fast WiFi and seasonal window AC units
• Washer and dryer conveniently located off the kitchen

SLEEPING ARRANGEMENTS

• First floor: King bedroom with en-suite bathroom
• Second floor: Bedroom with two queen beds
• Second floor: Bedroom with one king and two twin beds
• Second floor: Sitting area and reading nook with daybed for lounging; not included in guest capacity

LOCATION HIGHLIGHTS

• 10 minutes to Catamount Mountain Resort
• 25 minutes to Hudson, NY
• 30 minutes to Great Barrington, MA
• Close to hiking, farm stands, restaurants, galleries, and shops
• Convenient to both the Hudson Valley and the Berkshires

PERFECT FOR

• Families and friends gathering for a weekend away
• Summer pool getaways
• Ski and snowboard trips to Catamount
• Guests who appreciate distinctive, collected interiors
• Groups wanting privacy with space to spread out
• Hudson Valley and Berkshires explorers

READY TO UNWIND?

Private Hillsdale homes with pools, mountain views, and space for the whole group are especially sought-after during summer and ski season. Secure your dates and start looking forward to poolside afternoons, fireside evenings, and effortless time together.

Guests will have full access to the home. The garage is off limits. In the basement the areas available to guests are the mudroom, and living and game room areas. Any back stock, storage, or stored owner/house items etc. is off limits.

The best way to reach us is by messaging us through the Airbnb App inbox.

This is a rural country property surrounded by woods and native wildlife. Deer, wild turkeys, bears, insects, mice, and other animals may occasionally be seen in the area. While the home is professionally maintained and regularly serviced, seasonal encounters with insects or other country critters can happen.

The private pool is unheated and typically available from Memorial Day through October, depending on weather and seasonal maintenance.

Seasonal window AC units are installed during warmer months. The traditional fireplace in the library is decorative and not available for guest use; the wood stove in the sunroom is operational.

The driveway slopes through the property. AWD or 4WD is strongly recommended during winter weather, and guests should arrive prepared for rural driving conditions.

Exterior Ring cameras are located at the entry doors and monitor the entrances only. There are no cameras inside the home or in private guest areas.

This is a pet-free property.