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Compare 8 Villas in Hillsdale with updated reviews, rates, and availability.

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

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
The Kemble - a registered Great Estate

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
The Winthrop (1)

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
Outdoor Swimming Pool

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
Property grounds

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
Aerial view of the front of the house.

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
Living Room

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
Living area

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
Terrace/patio

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 SAR 488
SAR 527 total
includes taxes & fees
9 Jan - 10 January 2025
Micosta Leisure Inn
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
The Cabin Overlooking Chloe's Lake

'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 SAR 470
SAR 545 total
includes taxes & fees
29 Dec - 30 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (231)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is SAR 548
SAR 839 total
includes taxes & fees
30 Dec - 31 Dec
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.

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