Operated by a Wander partner
Trusted operators, vetted by Wander
Breezy Hill, Hillsdale, NY: Light-filled 70′s contemporary with multi-level decks with outdoor seating, propane grill, screened porch, pond with dingy and floating dock, outdoor shower, and beautiful Catskill views. Just 1 mile from Ski Catamount with the awesome aerial ropes course adventure park in summer! Amenities include: 4 bedrooms, 2 full baths - Sleeps 8 in beds or 9 max, high speed internet, Smart TV with access to all subscription TV channels, AC throughout, wood burning stove, 7+ acres of hiking and cross country trails on the property, pack-n-play available (please bring our own baby sheets) All house linens are included. House is 2600 Sq Ft and available for all seasons.
Breezy Hill has beautiful views of the Catskill Mountains, wrap-around decks, a screened porch, wood stove, and pond and more, just 1 mile from Ski Catamount. Guests come in through the front door and up a staircase to access the main living space. Once upstairs, the kitchen, dining room and living room are open concept and well situated, with a wall of glass sliders. This top level deck wraps around the living room and dining room and includes Adirondack chairs, table with umbrella, and a gas grill. The furnished screened porch is right off the kitchen and allows for outdoor enjoyment and dining al fresco. The kitchen has stainless appliances, storage and counter space, and plenty of cooking gadgets. This upper level also has the ensuite primary bedroom with a Queen bed and full bathroom with tub/shower combination.
The lower/main floor has 3 bedrooms: Guest room #2 has a King bed, Guest room #3 has a Queen bed plus a small fold out futon bed, and Guest room #4 has 2 twin beds. These 3 guest rooms all share a newly redone full bathroom with a shower. There is also an outdoor shower with hot/cold running water, available seasonally. The media room is also on this main floor and has a Smart TV with access to your subscription TV channels! This room also has sliding doors that lead to the lower deck - also with outdoor seating. The washer and dryer are located in the basement and the access to the outdoor shower is either through the basement or from the back yard. There is a Pack N Play available (guest brings their own sheets).
Outside, features include a pond with a floating dock, a small creek running along the edge of the property, and 7+ acres of land to explore and hike. Please note, Fishing in the pond is catch and release only In winter, just step out the front door for great sledding, snowshoeing or skating on the pond - only when weather conditions permit.
The house is perfectly located - less than 30 minutes to Hudson for great food, art galleries and antiquing. 15 minutes to Great Barrington for food, shops and restaurants. For hikers, Bash Bish Falls is a 10 minute drive as is the Appalachian Trail.
For skiers you are only one mile from Catamount or 20 minutes to Butternut. Summer renters can enjoy this remote location but still be within a short drive to all the cultural events the Berkshires are known for.
Breezy Hill is pet friendly, however, pets must be approved and, typically, a $150 minimum pet fee applies. (Cats are not permitted due to allergies.)
Non Smoking, Thank you!
Bedroom 1
1 queen bed
Bedroom 2
1 king bed
Bedroom 3
2 twin beds
Bedroom 4
1 queen bed
Bedroom 1
1 queen bed
Bedroom 2
1 king bed
Bedroom 3
2 twin beds
Bedroom 4
1 queen bed
Hillsdale, NY 12529, US
Hillsdale, NY, USNestled at the base of Catamount Mountain, Little Cat Lodge serves authentic American cuisine with a stellar wine list in a cozy Alpine chalet ambiance, complete with a roaring fireplace and sunroom perfect for post-ski unwinding.[1][2][3]
Zinnia’s Dinette serves up New England-style fish fries with flaky, beer-battered cod, fresh clams, oysters, and fried chicken in a cozy indoor space and huge outdoor yard. This Craryville gem blends retro diner vibes with high-end casual eats that draw crowds from afar.
Nestled in a restored 1850s Hillsdale mercantile, Roe Jan Brewing Co. pairs balanced craft beers with wood-fired, from-scratch pub fare like grilled meats and farm-fresh veggies. Unwind around the vintage grain hopper bar, on dog-friendly patios, or amid live music in this historic brewpub gem.
Discover The Mill, where hearty comfort food, sandwiches, and wood-fired pizzas shine with top-quality ingredients. Unwind in its rustic upstairs dining room—BYOB welcome—for a cozy, neighborly vibe.[1]
Nestled in a historic harness shop, Twisted Sisters Coffee House offers a witchy, warm ambiance with all-day breakfast, fresh-baked scones and muffins, hearty sandwiches, and the best lattes in town. It's a cozy oasis for coffee lovers craving flavorful treats and homemade sweets.[1][2]
Discover Massachusetts' tallest single-drop waterfall at Bash Bish Falls State Park, where twin 80-foot cascades thunder into an emerald pool amid ancient forests. Nature lovers and hikers seeking a short, rewarding trail with breathtaking views will love this Berkshires gem.[1][3][4]
Conquer the challenging 6-mile Alander Mountain Trail through hemlock forests, rocky scrambles, and meadows to a stunning panoramic summit with 360-degree views of the Berkshires, Catskills, and beyond. Perfect for avid hikers and backpackers craving adventure and solitude.
Discover breathtaking Berkshire mountain views on Jug End State Reservation's easy 3-4 mile loop trail, weaving through open meadows, hemlock forests, and historic apple orchards once planted by Johnny Appleseed. Nature lovers, families, and casual hikers will cherish its serene wilderness escape.[1][2][4][5]
Discover the serene beauty of Roeliff Jansen Park, where easy trails wind through rolling fields, past a sparkling stream, dog run, and picnic groves with stunning valley views. Families, nature lovers, and dog owners will cherish this volunteer-run gem blending adventure and community vibes.
Taconic State Park's Copake Falls area offers stunning natural scenery with waterfalls, scenic overlooks, and historic sites, making it perfect for hikers, nature lovers, and outdoor enthusiasts seeking a peaceful escape in the Hudson Valley region.
Experience one of New England's largest aerial adventure parks featuring 9 tree-top courses with bridges, ladders, and zip lines suspended through the canopy, perfect for thrill-seekers and first-time climbers alike seeking an unforgettable outdoor challenge.
Discover over 30 miles of trails in Mount Washington State Forest's lush red oak forest, hiking or mountain biking to Alander Mountain's stunning 2,250-ft summit views. Nature lovers and adventure seekers will relish this rustic escape.[2][7]
Discover the magical twilight courtship of secretive woodcocks—timberdoodles—at French Park, where nasal peents and daring sky dives unfold under the full moon. Nature lovers and birdwatchers will love this worm-eating daredevil spectacle during their northern migration.[1]
Soar through New England's largest aerial adventure park at Catamount, tackling 9 challenging courses with over 150 obstacles, zip lines, and tree-top thrills for 3 hours of heart-pounding fun. Perfect for families, thrill-seekers aged 7+, and anyone conquering heights amid stunning Hudson Valley views.[1][2][5]
Discover the Copake Iron Works Historic Site, one of the Northeast's most intact 19th-century ironworks with its towering blast furnace, original buildings, and a charming replica railroad ride. History buffs, families, and outdoor explorers will love this immersive glimpse into industrial heritage amid scenic Taconic State Park.
50% refund up to 30 days before check-in. No refund after that.
Pets allowed with fee
No smoking - fees will apply
Events not allowed
Check-in after 3:00 pm
Check-out before 11:00 am
9 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
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| Jul 13, 2026 | $700 | Not Available |
| Jul 14, 2026 | $700 | Not Available |
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| Sep 8, 2026 | $475 | Not Available |
| Sep 9, 2026 | $475 | Not Available |
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| Sep 11, 2026 | $475 | Not Available |
| Sep 12, 2026 | $475 | Not Available |
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| Oct 8, 2026 | $475 | Available |
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| Oct 10, 2026 | $475 | Not Available |
| Oct 11, 2026 | $475 | Not Available |