Book Guest Houses in Chester, MA
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Top Guest Houses in Chester
Hideaway Inn Lenox
11 Old Stockbridge Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$151 nightly
The price is $169 total per night
$169 total
Aug 9 - Aug 10
Total with taxes and fees
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the arcade/game room and picnic area. A communal living room, a library, and a virtual front desk are also on offer.
Pet friendly
Parking included
The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
$91 nightly
The price is $102 total per night
$102 total
Sep 3 - Sep 4
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!!
Lanesborough MA
$200 nightly
The price is $223 total per night
$223 total
Aug 31 - Sep 1
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!
Granby CT
$220 nightly
The price is $249 total per night
$249 total
Aug 9 - Aug 10
Total with taxes and fees
A garden is available at this guesthouse.
Air conditioning
Parking available
The Dewey
7 Hubbard Street Lenox MA
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.
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!
Granby CT
This guesthouse includes a garden and laundry facilities.
Air conditioning
Parking available
Hill Ross Guest Suite on Historic Homestead
Florence MA
This guesthouse features a garden, laundry facilities, and barbecue grills.
Breakfast included
Air conditioning
Cliffwood Cottage by Evergreen Home
Lenox MA
This guesthouse features laundry facilities.
Free WiFi
Air conditioning
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
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
The Yankee Inn
461 Pittsfield Rd Lenox MA
$175 nightly
The price is $195 total per night from Aug 10 to Aug 11
$195 total
Aug 10 - Aug 11
Total with taxes and fees
9.2/10 Wonderful! (1,008 reviews)
Chester Guest Houses essential information
Accommodation | 10 Guest Houses |
|---|---|
Lowest Price | $102 |
Highest Price | $249 |
Popular accommodation | Hideaway Inn Lenox, The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, The Dewey, The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!, Hill Ross Guest Suite on Historic Homestead, Cliffwood Cottage by Evergreen Home, Jacob's Tanglewood Ranch, Chestnut Lodge |
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