Hillsdale Neighbors | Valley Views • Firepit

Exterior

Patio

Garden

Living Room

Kitchen

Bedroom 1

Bedroom 2

Bedroom 3

Bedroom 4

Ensuite Bathroom 1

Ensuite Bathroom 2

Ensuite Bathroom 3

Office

Common Area

Laundry Room

Hillsdale, NY

Hillsdale Neighbors | Valley Views • Firepit

4 bedrooms 4 beds 3 baths 8 guests

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) AvailabilityMin Stay (nights)
Apr 18, 2026$259Not Available3
Apr 19, 2026$247Not Available3
Apr 20, 2026$247Not Available3
Apr 21, 2026$258Not Available3
Apr 22, 2026$253Not Available3
Apr 23, 2026$256Not Available3
Apr 24, 2026$281Not Available3
Apr 25, 2026$269Not Available3
Apr 26, 2026$239Not Available3
Apr 27, 2026$228Not Available3
Apr 28, 2026$228Not Available3
Apr 29, 2026$237Not Available3
Apr 30, 2026$246Not Available3
May 1, 2026$310Not Available3
May 2, 2026$299Not Available3
May 3, 2026$261Not Available3
May 4, 2026$249Not Available3
May 5, 2026$250Not Available3
May 6, 2026$251Not Available3
May 7, 2026$254Not Available4
May 8, 2026$337Not Available4
May 9, 2026$325Not Available4
May 10, 2026$285Not Available4
May 11, 2026$276Not Available4
May 12, 2026$268Not Available4
May 13, 2026$261Not Available4
May 14, 2026$277Not Available4
May 15, 2026$382Not Available4
May 16, 2026$411Not Available4
May 17, 2026$358Not Available4
May 18, 2026$276Not Available4
May 19, 2026$276Not Available4
May 20, 2026$349Not Available4
May 21, 2026$342Available3
May 22, 2026$606Available3
May 23, 2026$625Available3
May 24, 2026$607Available3
May 25, 2026$382Available3
May 26, 2026$277Available3
May 27, 2026$278Available3
May 28, 2026$352Available3
May 29, 2026$393Available3
May 30, 2026$401Available3
May 31, 2026$323Available3
Jun 1, 2026$313Available3
Jun 2, 2026$349Available3
Jun 3, 2026$296Available3
Jun 4, 2026$353Available3
Jun 5, 2026$392Available3
Jun 6, 2026$417Available3
Jun 7, 2026$344Available3
Jun 8, 2026$324Available3
Jun 9, 2026$310Available3
Jun 10, 2026$312Available3
Jun 11, 2026$399Available3
Jun 12, 2026$501Available3
Jun 13, 2026$499Available3
Jun 14, 2026$397Available3
Jun 15, 2026$356Available3
Jun 16, 2026$343Available4
Jun 17, 2026$389Available4
Jun 18, 2026$566Available4
Jun 19, 2026$656Available4
Jun 20, 2026$622Available4
Jun 21, 2026$502Available4
Jun 22, 2026$401Available4
Jun 23, 2026$413Available4
Jun 24, 2026$465Available4
Jun 25, 2026$628Not Available5
Jun 26, 2026$721Not Available5
Jun 27, 2026$718Not Available5
Jun 28, 2026$603Not Available5
Jun 29, 2026$554Not Available5
Jun 30, 2026$589Not Available5
Jul 1, 2026$692Not Available5
Jul 2, 2026$799Not Available5
Jul 3, 2026$799Not Available5
Jul 4, 2026$799Not Available5
Jul 5, 2026$631Not Available5
Jul 6, 2026$580Not Available7
Jul 7, 2026$497Not Available7
Jul 8, 2026$564Not Available7
Jul 9, 2026$645Not Available7
Jul 10, 2026$703Not Available7
Jul 11, 2026$672Not Available7
Jul 12, 2026$561Not Available7
Jul 13, 2026$608Not Available7
Jul 14, 2026$481Not Available7
Jul 15, 2026$492Not Available7
Jul 16, 2026$583Not Available7
Jul 17, 2026$672Not Available7

Where you'll sleep

Amenities

Hot tub
Fire place
BBQ Area
Dryer
Air conditioning
Kitchen
Smoke detector
First aid kit

Guests love this place

4.8

based on 5 reviews

Overall rating

5
4
3
2
1
J
Jen L.
about 2 months ago

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.

A
Armando T.
about 2 months ago

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!

B
Brian M.
about 2 months ago

Beautiful space, secluded and comfortable. Jaryn is an excellent host, highly recommend!

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

Things to know

Cancellation policy

Cancel within 24 hours for a full refund.
Fair-Refund policy applies after the cancellation deadline.

Property rules

Not suitable for children (2–12 years).
Not suitable for infants (under 2).
Pets allowed.
No parties or events.

Safety & security

Check-in after 3:00 PM.
Check-out before 11:00 AM.
Maximum 8 guests.