Villas in Sheffield

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Compare 7 Villas in Sheffield with updated reviews, rates, and availability.

The Freeman - Newly Renovated 14K SF Estate on 40 Acres
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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
The Kemble- Built by a US Secretary of State in Lenox
Exterior
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (15)
"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, (2)
"Absolutely stunning property - truly incredible stay. Recommend to anyone looking for a large group getaway. Fast WiFi, commercial grade kitchen and plentiful supplies make it easy for large groups. beautiful property and room for activities on a huge lawn. Highly recommend."
The Winthrop Estate - 12K SF 32 Acres
5k+ Sq Ft of Luxury Living on 54 Acres near Hudson
Interior
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
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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.

Other property types in Sheffield

Cheerful 3-bedroom cottage with woodstove
Property grounds
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (22)
"This home was "as advertised" - plenty of room. Nice neighborhood setting. Well stocked kitchen & nice outside area in the backyard / deck. We used it as a base camp for section hiking the appalachian trail."
The price is $217
$479 total
includes taxes & fees
Jun 19 - Jun 20
Cheerful 3-bedroom cottage with woodstove
Antique Farmhouse Totally Restored
Exterior
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (80)
"We have 20 years experience renting homes for family gatherings and this is the most interesting and amazing property. Gardens galore, plenty of space to congregate or go off by yourself, fully appointed kitchen, and comfortable space. We were a party of ten and everyone loved the experience."
Antique Farmhouse Totally Restored
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
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.

Sheffield Villas information

Number of reviews
51
Accommodation
7 Villas
Lowest Price
Highest Price

Frequently asked questions

Why book your villa in Sheffield with Expedia?
Expedia makes it a cinch to find your ideal villa in Sheffield. Traveling with the kids? Make the most of our helpful filters to search for stays with a kitchen or a pool. If you’re sticking to a budget, select how much you’re willing to spend and your preferred star rating. We’ll help you find the perfect stay that suits your taste and style.
How can I find cheap villas in Sheffield?
Expedia is here to help you narrow your search for cheap villas in Sheffield. Use our convenient filter tool to choose star rating, amenities and budget to refine your search and find the best place to stay in a couple of quick clicks.
What is there to do near my villa in Sheffield?
Whatever you love to do, Sheffield has lots of things to keep you going. Ski Butternut, Bash Bish Falls State Park and Mahaiwe Performing Arts Center are on most travelers’ sightseeing itineraries. Don’t forget to explore Umpachene Falls Park, Mount Everett State Reservation and Les Trois Emme Winery either. With Expedia’s hotel deals in Sheffield, you can see more neat attractions like these with the cash you save.

Recent reviews of Sheffield hotels
Expedia verified reviews

Life House Berkshires

Life House Berkshires

5/5 Excellent
Modern, friendly and clean
"From my kind greeting from Bobby to my checkout in the morning, my stay could not have been better. Clean and up to date rooms, a great bar and friendly staff. Will definitely come back. "
A verified traveler stayed at Life House Berkshires
Posted 21 hours ago
Life House Berkshires