Book Guest Houses in Chester, MA

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Top Guest Houses in Chester

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St. Pittsfield MA
$85 nightly
The price is $95 total per night
$95 total
Dec 21 - Dec 22
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, express check-in, and express check-out are also on offer.
Pet friendly
Parking included
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough MA
$188 nightly
The price is $210 total per night
$210 total
Dec 21 - Dec 22
Total with taxes and fees
This guesthouse includes a garden and barbecue grills.
Free WiFi
Air conditioning
The Dewey

The Dewey

3.5 out of 5
7 Hubbard Street Lenox MA
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This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Parking included
Free WiFi
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

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

Granby CT
$237 nightly
The price is $269 total per night
$269 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This guesthouse features limo/town car service, a garden, and concierge services.
Air conditioning
Parking available
Jacob's Tanglewood Ranch

Jacob's Tanglewood Ranch

3 out of 5
560 Stockbridge Rd Lee MA
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This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a lobby fireplace, and a communal living room are also on offer.
Pet friendly
Parking included
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street Lee MA
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A hot tub is featured at this guesthouse, along with free self parking. WiFi in public areas is free. A terrace and a picnic area are also provided.
Hot Tub
Parking included
Cliffwood Cottage by Evergreen Home

Cliffwood Cottage by Evergreen Home

Lenox MA
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This guesthouse features laundry facilities.
Free WiFi
Air conditioning
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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.

Top hotels in Chester

D. Hotel Suites & Spa

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA
$128 nightly
The price is $143 total per night from Dec 21 to Dec 22
$143 total
Dec 21 - Dec 22
Total with taxes and fees
9.2/10 Wonderful! (2,259 reviews)

Chester Guest Houses essential information

Accommodation
7 Guest Houses
Lowest Price
$89
Highest Price
$269
Popular accommodation
The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Dewey, A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home

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