Hillsdale, NY
Breezy Hill
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
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Apr 24, 2026 | $375 | Not Available | 2 |
| Apr 25, 2026 | $375 | Not Available | 2 |
| Apr 26, 2026 | $375 | Not Available | 2 |
| Apr 27, 2026 | $375 | Not Available | 2 |
| Apr 28, 2026 | $375 | Not Available | 2 |
| Apr 29, 2026 | $375 | Not Available | 2 |
| Apr 30, 2026 | $375 | Available | 2 |
| May 1, 2026 | $375 | Not Available | 2 |
| May 2, 2026 | $375 | Not Available | 2 |
| May 3, 2026 | $375 | Not Available | 2 |
| May 4, 2026 | $375 | Not Available | 2 |
| May 5, 2026 | $375 | Not Available | 2 |
| May 6, 2026 | $375 | Not Available | 2 |
| May 7, 2026 | $375 | Not Available | 2 |
| May 8, 2026 | $375 | Not Available | 2 |
| May 9, 2026 | $375 | Not Available | 2 |
| May 10, 2026 | $375 | Not Available | 2 |
| May 11, 2026 | $375 | Not Available | 2 |
| May 12, 2026 | $375 | Not Available | 2 |
| May 13, 2026 | $375 | Not Available | 2 |
| May 14, 2026 | $375 | Not Available | 2 |
| May 15, 2026 | $466.67 | Not Available | 2 |
| May 16, 2026 | $466.67 | Not Available | 2 |
| May 17, 2026 | $466.67 | Not Available | 2 |
| May 18, 2026 | $466.67 | Not Available | 2 |
| May 19, 2026 | $466.67 | Not Available | 2 |
| May 20, 2026 | $466.67 | Not Available | 2 |
| May 21, 2026 | $550 | Not Available | 3 |
| May 22, 2026 | $550 | Not Available | 3 |
| May 23, 2026 | $550 | Not Available | 3 |
| May 24, 2026 | $550 | Not Available | 3 |
| May 25, 2026 | $550 | Not Available | 2 |
| May 26, 2026 | $550 | Not Available | 2 |
| May 27, 2026 | $550 | Not Available | 2 |
| May 28, 2026 | $550 | Not Available | 2 |
| May 29, 2026 | $550 | Not Available | 2 |
| May 30, 2026 | $550 | Not Available | 2 |
| May 31, 2026 | $550 | Not Available | 2 |
| Jun 1, 2026 | $575 | Not Available | 2 |
| Jun 2, 2026 | $575 | Not Available | 2 |
| Jun 3, 2026 | $575 | Not Available | 2 |
| Jun 4, 2026 | $575 | Not Available | 2 |
| Jun 5, 2026 | $575 | Not Available | 2 |
| Jun 6, 2026 | $575 | Not Available | 2 |
| Jun 7, 2026 | $575 | Not Available | 2 |
| Jun 8, 2026 | $575 | Not Available | 2 |
| Jun 9, 2026 | $575 | Not Available | 2 |
| Jun 10, 2026 | $575 | Not Available | 2 |
| Jun 11, 2026 | $575 | Not Available | 2 |
| Jun 12, 2026 | $575 | Not Available | 2 |
| Jun 13, 2026 | $575 | Available | 2 |
| Jun 14, 2026 | $550 | Not Available | 2 |
| Jun 15, 2026 | $550 | Not Available | 2 |
| Jun 16, 2026 | $550 | Not Available | 2 |
| Jun 17, 2026 | $550 | Not Available | 2 |
| Jun 18, 2026 | $550 | Not Available | 3 |
| Jun 19, 2026 | $550 | Not Available | 3 |
| Jun 20, 2026 | $550 | Not Available | 3 |
| Jun 21, 2026 | $550 | Not Available | 3 |
| Jun 22, 2026 | $550 | Not Available | 3 |
| Jun 23, 2026 | $550 | Not Available | 3 |
| Jun 24, 2026 | $550 | Not Available | 3 |
| Jun 25, 2026 | $550 | Not Available | 3 |
| Jun 26, 2026 | $550 | Not Available | 3 |
| Jun 27, 2026 | $434 | Not Available | 30 |
| Jun 28, 2026 | $466.67 | Available | 30 |
| Jun 29, 2026 | $466.67 | Available | 30 |
| Jun 30, 2026 | $466.67 | Available | 30 |
| Jul 1, 2026 | $466.67 | Available | 30 |
| Jul 2, 2026 | $466.67 | Available | 30 |
| Jul 3, 2026 | $466.67 | Available | 30 |
| Jul 4, 2026 | $466.67 | Available | 30 |
| Jul 5, 2026 | $466.67 | Available | 30 |
| Jul 6, 2026 | $466.67 | Available | 30 |
| Jul 7, 2026 | $466.67 | Available | 30 |
| Jul 8, 2026 | $466.67 | Available | 30 |
| Jul 9, 2026 | $466.67 | Available | 30 |
| Jul 10, 2026 | $466.67 | Available | 30 |
| Jul 11, 2026 | $466.67 | Available | 30 |
| Jul 12, 2026 | $466.67 | Available | 30 |
| Jul 13, 2026 | $466.67 | Available | 30 |
| Jul 14, 2026 | $466.67 | Available | 30 |
| Jul 15, 2026 | $466.67 | Available | 30 |
| Jul 16, 2026 | $466.67 | Available | 30 |
| Jul 17, 2026 | $466.67 | Available | 30 |
| Jul 18, 2026 | $466.67 | Available | 30 |
| Jul 19, 2026 | $466.67 | Available | 30 |
| Jul 20, 2026 | $466.67 | Available | 30 |
| Jul 21, 2026 | $466.67 | Available | 30 |
| Jul 22, 2026 | $466.67 | Available | 30 |
| Jul 23, 2026 | $466.67 | Available | 30 |
Where you'll sleep
Amenities
Guests love this place
4.96
based on 25 reviews
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!
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!
Thanks for being communicative and sharing your home! Thanks so much for being communicative and sharing your home with us
4.96
based on 25 reviews
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!
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!
Thanks for being communicative and sharing your home! Thanks so much for being communicative and sharing your home with us
A perfect retreat This was my second year vacationing at Breezy Hill with my grown children and granddaughter, and I am already looking forward to our next time. The view from the house is absolutely spectacular, as are the grounds and the surrounding vistas. The house itself is extremely comfortable (great beds!) and ideally suited for a family or other guests because of the two levels. I also loved its location close to Great Barrington and with relatively easy access to Tanglewood, Stockbridge, and Chatham NY. I highly recommend Breezy Hill if you’re looking for a fabulous vacation.
The views were incredible We had a great visit , the views were incredible and the property was lovely to walk around and play on. We came with grandparents, kids, and a dog, and everyone had a great time. The home is snug but airy and never felt tight for us. We had great dinners on the deck . We explored the nearby hikes, water holes, farmers market, and restaurant. The house is secluded, and peaceful. We would come again.
Gorgeous View! Absolutely beautiful property with gorgeous view. Everything was clean and comfortable. Fully stocked kitchen. A lovely location for our getaway. We are already planning our next stay.
Lovely location! Absolutely beautiful property with gorgeous view. Everything was clean and comfortable. Fully stocked kitchen. A lovely location for our getaway. We are already planning our next stay.
Great Great, clean house minutes from catamount.
Comfortable cabin Great spot for family with kids near catamount. Comfortable cabin, beautiful views!
Wonderful This house was wonderful! We also appreciate that the owner was willing to accommodate our request to switch our stay when some of our party couldn’t make it. Overall the hosts were responsive and communicative and the property was beautiful.
Where you'll be
Hillsdale, NY, 12529, US
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
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