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Compare 275 Vacation Homes in Chester with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (240)
The price is SAR 563
SAR 855 total
includes taxes & fees
31 Mar - 1 Apr

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
10.0 out of 10, Exceptional, (149)

Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (211)

Heart of Lenox Walk to Town Cozy Cottage!
Heart of Lenox Walk to Town Cozy Cottage!
10.0 out of 10, Exceptional, (69)

Owl's Nest - Cozy Westfield Home w/ Fire Pit
Owl's Nest - Cozy Westfield Home w/ Fire Pit
9.4 out of 10, Exceptional, (3)

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
10.0 out of 10, Exceptional, (3)

Hilltown Nest is a wonderful place for family and friends to gather.
Hilltown Nest is a wonderful place for family and friends to gather.
9.8 out of 10, Exceptional, (15)

Mountain Blossom Retreat by Evergreen Home
Mountain Blossom Retreat by Evergreen Home
10.0 out of 10, Exceptional, (5)
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

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (240)
The price is SAR 563
SAR 855 total
includes taxes & fees
31 Mar - 1 Apr

The Ponds at Foxhollow
The Ponds at Foxhollow
8.6 out of 10, Excellent, (120)

The Clearing - Quiet - Close To Nature
The Clearing - Quiet - Close To Nature
10.0 out of 10, Exceptional, (187)
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.
Recent reviews of Chester hotels
Recent reviews of Chester hotels

The Ellery
5/5 Excellent
"We had a fantastic stay at the Ellery! From the moment we arrived, we were warmly welcomed, and the check-in process was seamless. Our room was spotless, spacious, and beautifully modern, with all the amenities we needed for a comfortable stay.
The highlight was definitely the breakfast—so generous and thoughtfully curated! We loved the fresh avocado toast, the variety of gluten-free options, and the organic coffee and teas. Every detail felt intentional and well-executed. And the fire in the fireplace was just the cherry on top!
"
A verified traveler stayed at The Ellery
Posted 9 hours ago