Photo by Elizabeth Massa Peroulakis

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Compare 7 Guest Houses in Chester with updated reviews, rates, and availability.

The Central Downtown Inn & Suites
Exterior

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (267)
"I loved all the amenities and space provided in the suite. And it was very affordable. It was like staying in an apartment. It was very clean. The bedroom wall was thin though because I could hear snoring on the other side. Pretty view of the trees in the backyard."
The Central Downtown Inn & Suites
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!
Exterior

The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

10.0 out of 10, Exceptional, (82)
"Fits our regular travel between Boston and Albany"
The price is SAR 432
SAR 910 total
includes taxes & fees
25 Nov - 26 Nov
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!
Romantic weekend getaway!

Romantic weekend getaway!

9.8 out of 10, Exceptional, (52)
"This is by far the best place we have ever stayed. From the beautiful gardens to the hummingbirds drinking nectar from the flowers, from the beautiful suite where the hosts have thought of everything to the great bathroom and calming shower, from the relaxing hot tub to the cooling and revitalizing pool, from the peaceful fire pit to the convenient gas grill, from the comfy couch to the supportive bed, from the ice maker to the fridge and freezer, from the oven to the stove top and even the...
Romantic weekend getaway!
The Retreat at Norwich Lake
Front of property

The Retreat at Norwich Lake

3.0 star property
9.8 out of 10, Exceptional, (17)
" You drive on an unpaved road for quite a while to get to the Inn. Once you get there, there is the most beautiful place that looks like a large log cabin. It is right on the lake and there are trees everywhere. One of the most beautiful areas that I’ve been to. The room is huge and very comfortable. I also had a balcony that overlooked the lake. Perfect to sit with a glass of wine and stare at the sights."
The Retreat at Norwich Lake
Jacob's Tanglewood Ranch
Exterior

Jacob's Tanglewood Ranch

3.0 star property
Jacob's Tanglewood Ranch
Chestnut Lodge
Exterior

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
Fair Vacation Rental 2
Exterior

Fair Vacation Rental 2

2.0 star property
Fair Vacation Rental 2
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!
Chester Vacation Rental | 2BR | 1BA | 2,000 Sq Ft | Stairs Required

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!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is SAR 537
SAR 830 total
includes taxes & fees
25 Nov - 26 Nov
Berkshire Village Carriage House - Super Private!!
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
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.