Hillsdale, NY
Hillsdale Neighbors | Valley Views • Firepit
About the property
Welcome to Hilltop Hillsdale House — your peaceful countryside retreat in the heart of Hillsdale. This spacious 4-bedroom, 3-bath home offers comfort, charm, and stunning views of rolling hills. Spend your days exploring Bash Bish Falls, skiing at Catamount, or biking along the Harlem Valley Rail Trail. After a day of adventure, relax on the porch, share meals with loved ones, and enjoy cozy evenings surrounded by nature’s beauty. The perfect escape for every season! ✔ High-speed Wi-Fi ✔ Smart TV ✔ Fully equipped kitchen ✔ Washer & dryer ✔ Free parking ✔ Air conditioning ✔ Private home office and library space ✔ Breathtaking porch views and large backyard with firepit ✔ Pet-friendly ✔ Pack n Play Travel Crib (Upon request) ➥ 7 mins to Harlem Valley rail trail ➥ 11 mins to Catamount ski area ➥ 17 mins to Bash Bish Falls ➥ 18 mins to W.E.B. Du Bois National Historic Site ➥ 29 mins to Ski Butternut ✦BEDS & BATHS✦ Inside we have 4 bedrooms and 3 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience. Room Breakdown: Main Bedroom - 1 Queen bed Bedroom 2 - 1 Queen bed Bedroom 3 - 1 Queen bed Bedroom 4 - 1 Double bed All Berkshire Vacation Rental Co.™ Properties include: - Support from full-time local team available daily from 9am to 9pm - Professional housekeeping & property inspection prior to guest arrival - Towels, linens, and bath products - At least a mornings worth of coffee to get you started - Learn more @berkshire vacation rental Cleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property. • DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized. To provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn't rectified. There is space for parking multiple cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.
Welcome to Hilltop Hillsdale House — your peaceful countryside retreat in the heart of Hillsdale. This spacious 4-bedroom, 3-bath home offers comfort, charm, and stunning views of rolling hills. Spend your days exploring Bash Bish Falls, skiing at Catamount, or biking along the Harlem Valley Rail Trail. After a day of adventure, relax on the porch, share meals with loved ones, and enjoy cozy evenings surrounded by nature’s beauty. The perfect escape for every season! ✔ High-speed Wi-Fi ✔ Smart TV ✔ Fully equipped kitchen ✔ Washer & dryer ✔ Free parking ✔ Air conditioning ✔ Private home office and library space ✔ Breathtaking porch views and large backyard with firepit ✔ Pet-friendly ✔ Pack n Play Travel Crib (Upon request) ➥ 7 mins to Harlem Valley rail trail ➥ 11 mins to Catamount ski area ➥ 17 mins to Bash Bish Falls ➥ 18 mins to W.E.B. Du Bois National Historic Site ➥ 29 mins to Ski Butternut ✦BEDS & BATHS✦ Inside we have 4 bedrooms and 3 bathrooms all decorated tastefully to give the full nostalgic Berkshire travel experience. Room Breakdown: Main Bedroom - 1 Queen bed Bedroom 2 - 1 Queen bed Bedroom 3 - 1 Queen bed Bedroom 4 - 1 Double bed All Berkshire Vacation Rental Co.™ Properties include: - Support from full-time local team available daily from 9am to 9pm - Professional housekeeping & property inspection prior to guest arrival - Towels, linens, and bath products - At least a mornings worth of coffee to get you started - Learn more @berkshire vacation rental Cleaning Protocols: As THE professional management company in The Berkshires we take pride in our professional cleaning standards between guests. We pay above the living wage & 100% of your cleaning fee is paid directly to the individual cleaner responsible for your property. • DOGS: Your dog is welcome and there is a one time fee of $100. Please include your pet in the booking so we know ahead of time. Max of 2 dogs. No other types of animals are authorized. To provide a high level of security and safety all Berkshire Vacation Rental Co. properties are equipped with a security camera facing the parking area and noise monitoring hardware inside the home. If either of these items are tampered with in any way guests will be alerted immediately and we reserve the right to cancel the reservation if the problem isn't rectified. There is space for parking multiple cars in the driveway. Please note, road and driveway of the property are gravel / dirt. Make sure to have an AWD equipped car in the winter months.
Availability & Pricing
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Apr 18, 2026 | $259 | Not Available | 3 |
| Apr 19, 2026 | $247 | Not Available | 3 |
| Apr 20, 2026 | $247 | Not Available | 3 |
| Apr 21, 2026 | $258 | Not Available | 3 |
| Apr 22, 2026 | $253 | Not Available | 3 |
| Apr 23, 2026 | $256 | Not Available | 3 |
| Apr 24, 2026 | $281 | Not Available | 3 |
| Apr 25, 2026 | $269 | Not Available | 3 |
| Apr 26, 2026 | $239 | Not Available | 3 |
| Apr 27, 2026 | $228 | Not Available | 3 |
| Apr 28, 2026 | $228 | Not Available | 3 |
| Apr 29, 2026 | $237 | Not Available | 3 |
| Apr 30, 2026 | $246 | Not Available | 3 |
| May 1, 2026 | $310 | Not Available | 3 |
| May 2, 2026 | $299 | Not Available | 3 |
| May 3, 2026 | $261 | Not Available | 3 |
| May 4, 2026 | $249 | Not Available | 3 |
| May 5, 2026 | $250 | Not Available | 3 |
| May 6, 2026 | $251 | Not Available | 3 |
| May 7, 2026 | $254 | Not Available | 4 |
| May 8, 2026 | $337 | Not Available | 4 |
| May 9, 2026 | $325 | Not Available | 4 |
| May 10, 2026 | $285 | Not Available | 4 |
| May 11, 2026 | $276 | Not Available | 4 |
| May 12, 2026 | $268 | Not Available | 4 |
| May 13, 2026 | $261 | Not Available | 4 |
| May 14, 2026 | $277 | Not Available | 4 |
| May 15, 2026 | $382 | Not Available | 4 |
| May 16, 2026 | $411 | Not Available | 4 |
| May 17, 2026 | $358 | Not Available | 4 |
| May 18, 2026 | $276 | Not Available | 4 |
| May 19, 2026 | $276 | Not Available | 4 |
| May 20, 2026 | $349 | Not Available | 4 |
| May 21, 2026 | $342 | Available | 3 |
| May 22, 2026 | $606 | Available | 3 |
| May 23, 2026 | $625 | Available | 3 |
| May 24, 2026 | $607 | Available | 3 |
| May 25, 2026 | $382 | Available | 3 |
| May 26, 2026 | $277 | Available | 3 |
| May 27, 2026 | $278 | Available | 3 |
| May 28, 2026 | $352 | Available | 3 |
| May 29, 2026 | $393 | Available | 3 |
| May 30, 2026 | $401 | Available | 3 |
| May 31, 2026 | $323 | Available | 3 |
| Jun 1, 2026 | $313 | Available | 3 |
| Jun 2, 2026 | $349 | Available | 3 |
| Jun 3, 2026 | $296 | Available | 3 |
| Jun 4, 2026 | $353 | Available | 3 |
| Jun 5, 2026 | $392 | Available | 3 |
| Jun 6, 2026 | $417 | Available | 3 |
| Jun 7, 2026 | $344 | Available | 3 |
| Jun 8, 2026 | $324 | Available | 3 |
| Jun 9, 2026 | $310 | Available | 3 |
| Jun 10, 2026 | $312 | Available | 3 |
| Jun 11, 2026 | $399 | Available | 3 |
| Jun 12, 2026 | $501 | Available | 3 |
| Jun 13, 2026 | $499 | Available | 3 |
| Jun 14, 2026 | $397 | Available | 3 |
| Jun 15, 2026 | $356 | Available | 3 |
| Jun 16, 2026 | $343 | Available | 4 |
| Jun 17, 2026 | $389 | Available | 4 |
| Jun 18, 2026 | $566 | Available | 4 |
| Jun 19, 2026 | $656 | Available | 4 |
| Jun 20, 2026 | $622 | Available | 4 |
| Jun 21, 2026 | $502 | Available | 4 |
| Jun 22, 2026 | $401 | Available | 4 |
| Jun 23, 2026 | $413 | Available | 4 |
| Jun 24, 2026 | $465 | Available | 4 |
| Jun 25, 2026 | $628 | Not Available | 5 |
| Jun 26, 2026 | $721 | Not Available | 5 |
| Jun 27, 2026 | $718 | Not Available | 5 |
| Jun 28, 2026 | $603 | Not Available | 5 |
| Jun 29, 2026 | $554 | Not Available | 5 |
| Jun 30, 2026 | $589 | Not Available | 5 |
| Jul 1, 2026 | $692 | Not Available | 5 |
| Jul 2, 2026 | $799 | Not Available | 5 |
| Jul 3, 2026 | $799 | Not Available | 5 |
| Jul 4, 2026 | $799 | Not Available | 5 |
| Jul 5, 2026 | $631 | Not Available | 5 |
| Jul 6, 2026 | $580 | Not Available | 7 |
| Jul 7, 2026 | $497 | Not Available | 7 |
| Jul 8, 2026 | $564 | Not Available | 7 |
| Jul 9, 2026 | $645 | Not Available | 7 |
| Jul 10, 2026 | $703 | Not Available | 7 |
| Jul 11, 2026 | $672 | Not Available | 7 |
| Jul 12, 2026 | $561 | Not Available | 7 |
| Jul 13, 2026 | $608 | Not Available | 7 |
| Jul 14, 2026 | $481 | Not Available | 7 |
| Jul 15, 2026 | $492 | Not Available | 7 |
| Jul 16, 2026 | $583 | Not Available | 7 |
| Jul 17, 2026 | $672 | Not Available | 7 |
Where you'll sleep
Amenities
Guests love this place
4.8
based on 5 reviews
Overall rating
This house had the perfect vibes for a ski trip. We were only about 15 minutes from Catamount, and the winter scenery was absolutely beautiful—quiet, peaceful, and exactly what we were hoping for. We did have a few mishaps with our non-AWD car in the winter conditions, but Jaryn was responsive and understanding. He provided helpful resources to help get us out of the predicament. The home itself felt very cozy and welcoming. The kitchen is every chef’s dream, and our dog had an absolute blast roaming around, which was such a refreshing change from the city landscape.
The home is beautiful, can watch the sunrise over the hills to the east from the living room or enjoy it outside on the deck, very private, with great views of the surrounding landscape, very cozy in the winter. We had a great time!. Thanks Jaryn!
Beautiful space, secluded and comfortable. Jaryn is an excellent host, highly recommend!
4.8
based on 5 reviews
Overall rating
This house had the perfect vibes for a ski trip. We were only about 15 minutes from Catamount, and the winter scenery was absolutely beautiful—quiet, peaceful, and exactly what we were hoping for. We did have a few mishaps with our non-AWD car in the winter conditions, but Jaryn was responsive and understanding. He provided helpful resources to help get us out of the predicament. The home itself felt very cozy and welcoming. The kitchen is every chef’s dream, and our dog had an absolute blast roaming around, which was such a refreshing change from the city landscape.
The home is beautiful, can watch the sunrise over the hills to the east from the living room or enjoy it outside on the deck, very private, with great views of the surrounding landscape, very cozy in the winter. We had a great time!. Thanks Jaryn!
Beautiful space, secluded and comfortable. Jaryn is an excellent host, highly recommend!
Overall, the experience was quite good. Jaryn was very responsive, the house was clean, and the bed was clean and comfortable. One thing to note is that there is no TV in the living room. The only TV is in the first-floor suite, but it was not working. Also, the Wi-Fi signal in the basement was not very strong.
Place was great!!!! Love the story behind the house....Will definitely be coming back in the future!!!!
Where you'll be
Hillsdale, NY, 12529, United States of America
Discover the quiet elegance of the Hudson Valley in Hillsdale, where rural charm meets sophisticated outdoor recreation. Explore the nearby Copake Hillsdale Farmers Market for seasonal local treasures or spend an afternoon on the greens at Copake Country Club, both just a short drive away. Year-round adventure awaits at Catamount Mountain Resort and Catamount Aerial Adventure Park, while the scenic trails of Taconic State Park
Discover the quiet elegance of the Hudson Valley in Hillsdale, where rural charm meets sophisticated outdoor recreation. Explore the nearby Copake Hillsdale Farmers Market for seasonal local treasures or spend an afternoon on the greens at Copake Country Club, both just a short drive away. Year-round adventure awaits at Catamount Mountain Resort and Catamount Aerial Adventure Park, while the scenic trails of Taconic State Park
Things to know
Cancellation policy
Refundable Bookings
Cancellation deadlines:
- For stays under 15 nights, you may cancel or reschedule up to 14 days before check-in for a full refund. For stays 15 nights or longer, the cancellation window is 60 days.
- For some homes, a 30-day deadline applies — this will be clearly shown before you book.
- Cancellations must be submitted before 4 PM EST on the deadline day to qualify.
Fair-Refund Policy
If you cancel after the deadline:
- Berkshire Vacation Rental Co. will relist your dates and automatically refund you for any nights that rebook.
- The refund per night will be the lower of the original price or the rebooking rate. Nights that do not rebook are non-refundable.
Half-Now, Half-Later Bookings
- The first half of your payment is non-refundable.
- The second half may be refunded according to the standard cancellation policy above.
Non-Refundable Bookings
If you selected a Non-Refundable rate at checkout, the booking cannot be changed or canceled, and no refund will be issued.
Date Changes & Rebooking
Once a stay is canceled, you can't rebook the same dates yourself. If you need help choosing new dates, our Concierge team is happy to assist.
Transfers to Another Guest
You may transfer your booking to someone else at no charge. Just contact the Concierge with the new guest's name and email. The new guest must accept the transfer for it to take effect.
Policy Match Guarantee
If a better price is available for the same property on Airbnb or the owner's site, contact the Concierge — Berkshire Vacation Rental Co. will match it.
By completing your booking, you acknowledge and agree to Berkshire Vacation Rental Co.'s cancellation policy.
