Hillsdale, NY

Breezy Hill

4 bedrooms 5 beds 2 baths 9 guests 5.0 (25)

About the 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

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jun 11, 2026$575Not Available2
Jun 12, 2026$575Not Available2
Jun 13, 2026$575Not Available2
Jun 14, 2026$550Not Available2
Jun 15, 2026$550Not Available2
Jun 16, 2026$550Not Available2
Jun 17, 2026$550Not Available2
Jun 18, 2026$550Not Available3
Jun 19, 2026$550Not Available3
Jun 20, 2026$550Not Available3
Jun 21, 2026$550Not Available3
Jun 22, 2026$550Not Available3
Jun 23, 2026$550Not Available3
Jun 24, 2026$550Not Available3
Jun 25, 2026$550Not Available3
Jun 26, 2026$550Not Available3
Jun 27, 2026$434Not Available30
Jun 28, 2026$700Not Available7
Jun 29, 2026$700Not Available7
Jun 30, 2026$700Not Available7
Jul 1, 2026$700Not Available7
Jul 2, 2026$700Not Available7
Jul 3, 2026$700Not Available7
Jul 4, 2026$700Not Available7
Jul 5, 2026$700Not Available7
Jul 6, 2026$700Not Available7
Jul 7, 2026$700Not Available7
Jul 8, 2026$466.67Not Available7
Jul 9, 2026$700Not Available7
Jul 10, 2026$700Not Available7
Jul 11, 2026$700Not Available7
Jul 12, 2026$700Not Available7
Jul 13, 2026$700Not Available7
Jul 14, 2026$700Not Available7
Jul 15, 2026$700Not Available7
Jul 16, 2026$700Not Available7
Jul 17, 2026$700Not Available7
Jul 18, 2026$700Not Available7
Jul 19, 2026$700Not Available7
Jul 20, 2026$700Not Available7
Jul 21, 2026$700Not Available7
Jul 22, 2026$700Not Available7
Jul 23, 2026$700Not Available7
Jul 24, 2026$700Not Available7
Jul 25, 2026$700Not Available7
Jul 26, 2026$700Not Available7
Jul 27, 2026$700Not Available7
Jul 28, 2026$700Not Available7
Jul 29, 2026$700Not Available7
Jul 30, 2026$700Not Available7
Jul 31, 2026$700Not Available7
Aug 1, 2026$700Not Available7
Aug 2, 2026$700Not Available7
Aug 3, 2026$700Not Available7
Aug 4, 2026$700Not Available7
Aug 5, 2026$700Not Available7
Aug 6, 2026$700Not Available7
Aug 7, 2026$700Not Available7
Aug 8, 2026$700Not Available7
Aug 9, 2026$700Not Available7
Aug 10, 2026$700Not Available7
Aug 11, 2026$700Not Available7
Aug 12, 2026$700Not Available7
Aug 13, 2026$700Not Available7
Aug 14, 2026$700Not Available7
Aug 15, 2026$700Not Available7
Aug 16, 2026$700Not Available7
Aug 17, 2026$700Not Available7
Aug 18, 2026$700Not Available7
Aug 19, 2026$700Not Available7
Aug 20, 2026$700Not Available7
Aug 21, 2026$700Not Available7
Aug 22, 2026$700Not Available7
Aug 23, 2026$700Not Available7
Aug 24, 2026$700Not Available7
Aug 25, 2026$700Not Available7
Aug 26, 2026$700Not Available7
Aug 27, 2026$700Not Available7
Aug 28, 2026$700Not Available7
Aug 29, 2026$700Not Available7
Aug 30, 2026$700Not Available7
Aug 31, 2026$700Not Available7
Sep 1, 2026$700Not Available3
Sep 2, 2026$700Not Available3
Sep 3, 2026$700Not Available3
Sep 4, 2026$700Not Available3
Sep 5, 2026$700Not Available3
Sep 6, 2026$700Not Available2
Sep 7, 2026$700Not Available2
Sep 8, 2026$475Not Available2
Sep 9, 2026$475Not Available2

Amenities

Waterfront
Mountain view
Dryer
Hair dryer
Heating
Wifi
Bed linens
TV

5.0 · 25 reviews

J
Jessica W.
January 2026

If you're looking to ski Catamount this place is extremely convenient! If you're looking to ski Catamount this place is extremely convenient! It's less than a 5 min drive to the mountain! Overall we had a really nice stay. The house was perfect for our group of 6, providing enough space to hang out without feeling like we were on top of each other. The beds were very comfortable and the kitchen was well stocked for our cooking needs!

E
Elizabeth H.
December 2025

The house was perfect for our group. The house was perfect for our group of five adults…super cozy, comfortable, and set in the prettiest surroundings. Overall, such a peaceful, charming spot. Would definitely stay again!

E
Ethan G.
September 2025

Thanks for being communicative and sharing your home! Thanks so much for being communicative and sharing your home with us

Where you'll be

Hillsdale, NY, 12529, US

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Cancellation policy

Contact us for cancellation policy details prior to booking.

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
Pets allowed.
No parties or events.

Safety & security

Check-in after 3:00 PM.
Check-out before 11:00 AM.
Maximum 9 guests.