Hillsdale, NY

Breezy Hill

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9 guests
4 bedrooms
2 bathrooms
1000 sqft

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.

  • BBQ Area
  • Garden
9 guests
4 bedrooms
2 bathrooms
1000 sqft

  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 10:00 AM


About this property

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!

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!

Availability & Pricing

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Mar 13, 2026$217Not Available58
Mar 14, 2026$217Not Available58
Mar 15, 2026$325Not Available2
Mar 16, 2026$325Not Available2
Mar 17, 2026$325Not Available2
Mar 18, 2026$325Not Available2
Mar 19, 2026$325Not Available2
Mar 20, 2026$400Not Available2
Mar 21, 2026$400Not Available2
Mar 22, 2026$325Not Available2
Mar 23, 2026$325Not Available2
Mar 24, 2026$325Not Available2
Mar 25, 2026$325Not Available2
Mar 26, 2026$325Not Available3
Mar 27, 2026$400Not Available2
Mar 28, 2026$400Not Available2
Mar 29, 2026$325Not Available2
Mar 30, 2026$325Not Available2
Mar 31, 2026$325Not Available2
Apr 1, 2026$325Not Available2
Apr 2, 2026$375Not Available2
Apr 3, 2026$375Not Available2
Apr 4, 2026$375Not Available2
Apr 5, 2026$375Not Available2
Apr 6, 2026$375Not Available2
Apr 7, 2026$375Not Available2
Apr 8, 2026$375Not Available2
Apr 9, 2026$375Not Available2
Apr 10, 2026$375Not Available2
Apr 11, 2026$375Not Available2
Apr 12, 2026$375Not Available2
Apr 13, 2026$375Not Available2
Apr 14, 2026$375Not Available2
Apr 15, 2026$375Not Available2
Apr 16, 2026$375Not Available2
Apr 17, 2026$375Not Available2
Apr 18, 2026$375Not Available2
Apr 19, 2026$375Not Available2
Apr 20, 2026$375Not Available2
Apr 21, 2026$375Not Available2
Apr 22, 2026$375Not Available2
Apr 23, 2026$375Not Available2
Apr 24, 2026$375Not Available2
Apr 25, 2026$375Not Available2
Apr 26, 2026$375Not Available2
Apr 27, 2026$375Not Available2
Apr 28, 2026$375Not Available2
Apr 29, 2026$375Not Available2
Apr 30, 2026$375Not Available2
May 1, 2026$375Not Available2
May 2, 2026$375Not Available2
May 3, 2026$375Not Available2
May 4, 2026$375Not Available2
May 5, 2026$375Not Available2
May 6, 2026$375Not Available2
May 7, 2026$375Not Available2
May 8, 2026$375Not Available2
May 9, 2026$375Not Available2
May 10, 2026$375Not Available2
May 11, 2026$375Not Available2
May 12, 2026$375Not Available2
May 13, 2026$375Not Available2
May 14, 2026$375Not Available2
May 15, 2026$466.67Not Available2
May 16, 2026$466.67Not Available2
May 17, 2026$466.67Not Available2
May 18, 2026$466.67Not Available2
May 19, 2026$466.67Not Available2
May 20, 2026$466.67Not Available2
May 21, 2026$550Not Available3
May 22, 2026$550Not Available3
May 23, 2026$550Not Available3
May 24, 2026$550Not Available3
May 25, 2026$550Not Available2
May 26, 2026$550Not Available2
May 27, 2026$550Not Available2
May 28, 2026$550Not Available2
May 29, 2026$550Not Available2
May 30, 2026$550Not Available2
May 31, 2026$550Not Available2
Jun 1, 2026$575Not Available2
Jun 2, 2026$575Not Available2
Jun 3, 2026$575Not Available2
Jun 4, 2026$575Not Available2
Jun 5, 2026$575Not Available2
Jun 6, 2026$575Not Available2
Jun 7, 2026$575Not Available2
Jun 8, 2026$575Not Available2
Jun 9, 2026$575Not Available2
Jun 10, 2026$575Not Available2
Jun 11, 2026$575Not Available2

Top notch amenities

GUEST FAVORITES

BBQ Area
Patio
Garden
Hair dryer
Heating
Wifi
Bed linens
TV
Free parking

Where you'll sleep



Explore Hillsdale, NY

Immerse yourself in the year-round beauty of Hillsdale, where outdoor recreation and serene landscapes define the Berkshire experience. Nearby Catamount Mountain Resort and Catamount Aerial Adventure Park offer high-altitude excitement, while a short drive leads to the breathtaking cascades of Bash Bish Falls State Park and Taconic State Park - Copake Falls Area. Within easy reach, you can explore the expansive wilderness of Mount

Things to know

Here are some things which you should know before booking Breezy Hill

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
9 guests maximum
Pets allowed with fee (max 2)
No smoking - fees will apply
Events not permitted
Commercial photography requires approval