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Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Chester guest houses

A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

1. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (427 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
$99 nightly
The price is $111
Oct 21 - Oct 22
Total with taxes and fees
The Central Downtown Inn & Suites
A large white house with a prominent tower, surrounded by lush greenery and a well-maintained lawn.

2. Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very good, (63 reviews)
"Although the property was vintage, the rooms were clean and staff were very helpful and fun to be around. Parking and breakfast were included and the location was excellent."
United States
Barbara
$134 nightly
The price is $150
Nov 17 - Nov 18
Total with taxes and fees
Hideaway Inn Lenox
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.

3. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (300 reviews)
"Loved the easy Rail Trail access and peace and quite."
United States
Mary R.
$188 nightly
The price is $210
Oct 21 - Oct 22
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!
A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
10.0 out of 10, Exceptional, (117 reviews)
"We loved our stay! The cottage was adorable!"
United States
Kristen S.
$237 nightly
The price is $269
Nov 4 - Nov 5
Total with taxes and fees
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
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

Hotel On North

Hotel On North

10/10 Excellent
"Well maintained and updated property. Very kind and helpful team."
Michele 1-night trip
Posted 1 hour ago
Hotel On North

Find out more about Chester

Chester Guest Houses information

Number of reviews
844
Accommodation
10 Guest Houses
Lowest Price
$111
Highest Price
$269

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