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Browse Select Hillsdale Villas

The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Interior

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (16)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
The Winthrop Estate - 12K SF 32 Acres
Exterior

The Winthrop Estate - 12K SF 32 Acres

10.0 out of 10, Exceptional, (4)
"Everyone enjoyed the stay"
The Winthrop Estate - 12K SF 32 Acres
Catskill Villa/Pool with Hudson River View
Interior

Catskill Villa/Pool with Hudson River View

9.0 out of 10, Wonderful, (2)
"Really enjoyed our stay and the town."
Catskill Villa/Pool with Hudson River View
7 nights in our 1 br, full kitchen villa. Only 110 per night
Indoor pool, outdoor pool

7 nights in our 1 br, full kitchen villa. Only 110 per night

7 nights in our 1 br, full kitchen villa. Only 110 per night
5k+ Sq Ft of Luxury Living on 54 Acres near Hudson
Property grounds

5k+ Sq Ft of Luxury Living on 54 Acres near Hudson

8.0 out of 10, Very good, (5)
"Property was perfect for our group trip. The house was clean, spread out, well air-conditioned during the summer, and provided a number of sleeping options (easily sleeping 10). The outside was perfect for our guys-trip - lots of space, nice patio with overhang, and the pool was incredible. Overall the house was great, and Gautam was a great host - easy to communicate with, providing additional air mattresses and towels in every room. The house is 15-20 minutes from Hudson/Catskill towns, and...
5k+ Sq Ft of Luxury Living on 54 Acres near Hudson
Secluded Art & Architecture in Nature Retreat - hi
Interior

Secluded Art & Architecture in Nature Retreat - hi

Secluded Art & Architecture in Nature Retreat - hi
Mountain-View Retreat @ Heart of Hudson with Decks, Designer Decor & Game
Terrace/patio

Mountain-View Retreat @ Heart of Hudson with Decks, Designer Decor & Game

Mountain-View Retreat @ Heart of Hudson with Decks, Designer Decor & Game
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Hillsdale

Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (89)
"Fantastic place to stay! So homey, comfortable, and peaceful. Steven was a fabulous host, and his property is wonderful - in a beautiful garden. The room is large and beyond well equipped. No reason to pay more to stay downtown Hudson. We’re on a month-long New England road trip, and this has been our favorite stay! "
The price is CA $187
CA $201 total
includes taxes & fees
Jan 10 - Jan 11, 2025
Micosta Leisure Inn
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is CA $179
CA $208 total
includes taxes & fees
Jan 5 - Jan 6, 2025
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (232)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is CA $210
CA $321 total
includes taxes & fees
Dec 30 - Dec 31
Berkshire Village Carriage House - Super Private!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

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What is there to do near my villa in Hillsdale?
Once you’ve unpacked your suitcases, venture out and discover the amazing things Hillsdale has for you to experience. Catamount Aerial Adventure Park is a great attraction to add to your must-do list.