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Guest Houses in Chester

The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (307)
"Clean and convenient."
$105 nightly
The price is $117
Sep 8 - Sep 9
Total with taxes and fees
The Central Downtown Inn & Suites
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (321)
"excellent stay!! The Dewey is a cozy getaway location!"
$169 nightly
The price is $189
Sep 7 - Sep 8
Total with taxes and fees
The Dewey
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (256)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
$200 nightly
The price is $223
Sep 16 - Sep 17
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Exterior detail

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

10.0 out of 10, Exceptional, (88)
"Enjoyed staying"
$233 nightly
The price is $265
Sep 1 - Sep 2
Total with taxes and fees
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Jacob's Tanglewood Ranch
Dishwasher

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch
Chestnut Lodge
Property grounds

Chestnut Lodge

3.5 star property
2.0 out of 10, (2)
"An absolutely horrible experience! My family (2 adults and my 6 year old son) had reserved this so-called hotel for $284 in June for a 13th Aug stay. After a full day at the Berkshires, we checked-in at 6 pm. This place is in a terrible location (unpaved roads, still-in construction steps). To our horror we found that the room had No Air-Conditioning. It was 90 degrees outside and all they had in the room was a ceiling fan. There were bugs in the room due to the heat. On top of it all the...
Chestnut Lodge
Cliffwood Cottage by Evergreen Home
Interior

Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home
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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Top Chester Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."
James 5-night trip
Posted 4 hours ago
Berkshire Mountain Lodge