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
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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
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
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

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This vacation home includes a garden and barbecue grills.
Kitchen
Free WiFi
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

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

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This guesthouse features limo/town car service, a garden, and concierge services.
Air conditioning
Parking available
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

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

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This guesthouse includes a garden and laundry facilities.
Air conditioning
Parking available
Guest House Sanctuary by Evergreen Home

Guest House Sanctuary by Evergreen Home

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This guesthouse features a garden, laundry facilities, and barbecue grills.
Free WiFi
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

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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

D. Hotel Suites & Spa

D. Hotel Suites & Spa

1 Country Club Rd, Holyoke, MA
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9.2/10 Wonderful! (2,262 reviews)

Chester Guest Houses essential information

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

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