Compare Chester Guest House Rentals
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Featured Guest Houses in Chester
The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
$94 nightly
The price is $105 total per night
$105 total
Feb 15 - Feb 16
Total with taxes and fees
Guests of The Central Downtown Inn & Suites enjoy free WiFi in public areas, express check-in, and express check-out. If you drive, put free parking to good use. Staff members can help with accommodation requests, and provide luggage storage. Additional amenities include a terrace and laundry facilities.
Pet friendly
Parking included
Berkshire Village Carriage House - Super Private!!
Lanesborough MA
$188 nightly
The price is $210 total per night
$210 total
Jan 29 - Jan 30
Total with taxes and fees
Guests staying at this guesthouse have access to barbecue grills and a garden.
Free WiFi
Air conditioning
The Dewey
7 Hubbard Street Lenox MA
At The Dewey, guests have access to free WiFi in public areas, a meeting room, and a library. If you plan to drive, free parking is available. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include express check-out, free newspapers, and a terrace.
Parking included
Free WiFi
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby CT
$222 nightly
The price is $251 total per night
$251 total
Feb 9 - Feb 10
Total with taxes and fees
At this guesthouse, guests have access to a garden. Transportation is made easy with limo/town car service. Friendly staff can provide concierge services, and also offer advice about sightseeing.
Air conditioning
Parking available
Jacob's Tanglewood Ranch
560 Stockbridge Rd Lee MA
Guests staying at Jacob's Tanglewood Ranch enjoy free WiFi in public areas, a terrace, and a picnic area. You can take advantage of free parking if you drive. Additional amenities include a communal living room and barbecue grills.
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.
Hotel Options in Chester
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
$124 nightly
The price is $139 total per night from Jan 29 to Jan 30
$139 total
Jan 29 - Jan 30
Total with taxes and fees
9.2/10 Wonderful! (2,245 reviews)
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$121 nightly
The price is $136 total per night from Feb 26 to Feb 27
$136 total
Feb 26 - Feb 27
Total with taxes and fees
9/10 Wonderful! (818 reviews)
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
$98 nightly
The price is $109 total per night from Jan 30 to Jan 31
$109 total
Jan 30 - Jan 31
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
Chester Guest Houses essential information
Accommodation | 7 Guest Houses |
|---|---|
Lowest Price | $105 |
Highest Price | $251 |
Popular accommodation | The Central Downtown Inn & Suites, Berkshire Village Carriage House - Super Private!!, The Dewey, A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, Jacob's Tanglewood Ranch, Chestnut Lodge, Cliffwood Cottage by Evergreen Home |