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
$102 nightly
The price is $114 total per night
$114 total
Apr 6 - Apr 7
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
$185 nightly
The price is $207 total per night
$207 total
Apr 5 - Apr 6
Total with taxes and fees
This guesthouse includes a garden and barbecue grills.
Free WiFi
Air conditioning
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

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

Granby CT
$215 nightly
The price is $244 total per night
$244 total
Apr 6 - Apr 7
Total with taxes and fees
This guesthouse features limo/town car service, a garden, and concierge services.
Air conditioning
Parking available
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
Hill Ross Guest Suite on Historic Homestead

Hill Ross Guest Suite on Historic Homestead

Florence MA
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This guesthouse features a garden, laundry facilities, and barbecue grills.
Breakfast included
Kitchen
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

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

Granby CT
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This guesthouse includes a garden and laundry facilities.
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
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
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
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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

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

1080 Riverdale St West Springfield MA
$111 nightly
The price is $127 total per night from Apr 26 to Apr 27
$127 total
Apr 26 - Apr 27
Total with taxes and fees
9.6/10 Exceptional! (173 reviews)

Chester Guest Houses essential information

Accommodation
8 Guest Houses
Lowest Price
$114
Highest Price
$244
Popular accommodation
The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, The Dewey, Hill Ross Guest Suite on Historic Homestead, The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, Chestnut Lodge

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