Book Guest Houses in Chester, MA
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Top Guest Houses in Chester
The Central Downtown Inn & Suites
20 W Housatonic St., Pittsfield, MA
$104 nightly
The price is $116 total per night
$116 total
Oct 31 - Nov 1
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
The Dewey
7 Hubbard Street, Lenox, MA
$185 nightly
The price is $207 total per night
$207 total
Oct 29 - Oct 30
Total with taxes and fees
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!!
$205 nightly
The price is $229 total per night
$229 total
Oct 28 - Oct 29
Total with taxes and fees
This vacation home includes a garden and barbecue grills.
Kitchen
Free WiFi
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
$233 nightly
The price is $265 total per night
$265 total
Oct 22 - Oct 23
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
560 Stockbridge Rd, Lee, MA
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
75 Chestnut Street, Lee, MA
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
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
1 Country Club Rd, Holyoke, MA
$134 nightly
The price is $150 total per night from Oct 7 to Oct 8
$150 total
Oct 7 - Oct 8
Total with taxes and fees
9.2/10 Wonderful! (2,255 reviews)
Chester Guest Houses essential information
Accommodation | 7 Guest Houses |
|---|---|
Lowest Price | $93 |
Highest Price | $265 |
Popular accommodation | The Central Downtown Inn & Suites, The Dewey, Berkshire Village Carriage House - Super Private!!, A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home |
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