Photo by Elizabeth Massa Peroulakis

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Compare 5 Villas in Chester with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (4)
"Everyone enjoyed the stay"
The Winthrop Estate - 12K SF 32 Acres

Cozy Valley View Post & Beam Villa!

10.0 out of 10, Exceptional, (1)
"This was a family reunion of young adults and their parents. Everyone loved the house. Very well equipped kitchen. If the weather had been better there are gorgeous views out the back."
The price is SAR 2,817
SAR 3,596 total
includes taxes & fees
6 Jan - 7 January 2025
Cozy Valley View Post & Beam Villa!

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
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 Chester

Cozy Berkshires Vacation Rental Near Hiking!

10.0 out of 10, Exceptional, (1)
"The stay at the property was enjoyable. The space was large, spacious and very clean. Two people were able to stay quite comfortably."
Cozy Berkshires Vacation Rental Near Hiking!

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 SAR 548
SAR 839 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!

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.