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Compare 6 Villas in Sheffield 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
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
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 Sheffield

Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored
Cheerful 3-bedroom cottage with woodstove
great kitchen for cooking in

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (33)
"We stayed at this home about the same time last year and we were so happy with everything about it, we jumped at the opportunity to stay there again. The house has absolutely everything you'd need and is close to Canaan, CT and Great Barrington, MA and everything the Bershires have to offer. Sabrina is a great host and responded within minutes to any questions I had. We HIGHLY recommend this home."
The price is SAR 890
SAR 1,905 total
includes taxes & fees
5 Jan - 6 January 2025
Cheerful 3-bedroom cottage with woodstove
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (200)
"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"
Peace and quiet on the lake
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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