Book Guest Houses in Chester

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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.
Sweet Dreams Retreat

Sweet Dreams Retreat

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A water park and a spa tub are featured at this guesthouse. Families will appreciate the playground and barbecue grills. A garden is also provided.
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!

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

The price is $115 per night
$115
per night
May 5 - May 6
A garden is available at this guesthouse.
Guest House Sanctuary by Evergreen Home

Guest House Sanctuary by Evergreen Home

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This guesthouse includes a garden and barbecue grills.
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.
Chestnut Lodge

Chestnut Lodge

3.5 out of 5
75 Chestnut Street, Lee, MA
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A spa 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.
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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

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

1254 Riverdale Street, West Springfield, MA
The price is $76 per night from Apr 29 to Apr 30
$76
per night
Apr 29 - Apr 30
7/10 Good! (1,000 reviews)

Chester Guest Houses essential information

Accommodation
6 Guest Houses
Lowest Price
$76
Highest Price
$122
Popular accommodation
The Central Downtown Inn & Suites, Sweet Dreams Retreat, The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!, Guest House Sanctuary by Evergreen Home, Jacob's Tanglewood Ranch, Chestnut Lodge

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