Hillsdale, NY

Hillsdale Neighbors | Valley Views • Firepit

4 bedrooms 4 beds 3 baths 8 guests 4.8 (5)

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. 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. 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

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.

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
May 19, 2026$276Not Available4
May 20, 2026$349Not Available4
May 21, 2026$350Not Available3
May 22, 2026$623Not Available3
May 23, 2026$646Not Available3
May 24, 2026$627Not Available3
May 25, 2026$381Not Available3
May 26, 2026$251Not Available2
May 27, 2026$251Available2
May 28, 2026$292Available2
May 29, 2026$349Available2
May 30, 2026$365Available2
May 31, 2026$307Available2
Jun 1, 2026$277Available2
Jun 2, 2026$273Available2
Jun 3, 2026$237Available2
Jun 4, 2026$243Available2
Jun 5, 2026$281Available2
Jun 6, 2026$294Available2
Jun 7, 2026$234Available2
Jun 8, 2026$220Available2
Jun 9, 2026$216Available2
Jun 10, 2026$227Available2
Jun 11, 2026$279Available2
Jun 12, 2026$370Available2
Jun 13, 2026$362Available2
Jun 14, 2026$267Available2
Jun 15, 2026$230Available2
Jun 16, 2026$222Available2
Jun 17, 2026$244Available3
Jun 18, 2026$465Available3
Jun 19, 2026$561Available3
Jun 20, 2026$545Available3
Jun 21, 2026$424Available3
Jun 22, 2026$359Available3
Jun 23, 2026$363Available3
Jun 24, 2026$418Available3
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
Jul 18, 2026$644Not Available7
Jul 19, 2026$578Not Available7
Jul 20, 2026$487Not Available7
Jul 21, 2026$581Not Available7
Jul 22, 2026$508Not Available7
Jul 23, 2026$614Not Available7
Jul 24, 2026$749Not Available7
Jul 25, 2026$737Not Available7
Jul 26, 2026$639Not Available7
Jul 27, 2026$613Not Available7
Jul 28, 2026$603Not Available7
Jul 29, 2026$614Not Available7
Jul 30, 2026$625Not Available7
Jul 31, 2026$756Not Available7
Aug 1, 2026$740Not Available7
Aug 2, 2026$573Not Available7
Aug 3, 2026$527Not Available7
Aug 4, 2026$506Not Available7
Aug 5, 2026$523Not Available7
Aug 6, 2026$596Not Available7
Aug 7, 2026$757Not Available7
Aug 8, 2026$771Not Available7
Aug 9, 2026$556Not Available7
Aug 10, 2026$619Not Available7
Aug 11, 2026$543Not Available7
Aug 12, 2026$572Not Available7
Aug 13, 2026$651Not Available7
Aug 14, 2026$799Not Available7
Aug 15, 2026$799Not Available7
Aug 16, 2026$612Not Available7
Aug 17, 2026$596Not Available7

Where you'll sleep

Amenities

Fire pit
Outdoor fireplace
Fire place
Patio
Mountain view
Hammock
Kitchen
Dedicated workspace

4.8 · 5 reviews

J
Jen L.
January 2026

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.
January 2026

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.
January 2026

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

Where you'll be

Hillsdale, NY, 12529, US

Things to know

Cancellation policy

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 8 guests.