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
The price is $122 per night
$122
includes taxes & fees
$109 per night
May 6 - May 7
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
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
The price is $269 per night
$269
includes taxes & fees
$237 per night
May 8 - May 9
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
The Loft @ Lost Acres ~ A Peaceful Rural Escape on a Farm Winery!
The price is $242 per night
$242
includes taxes & fees
$213 per night
May 7 - May 8
At this guesthouse, guests have access to features like laundry facilities. This smoke-free guesthouse also has a garden.
Air conditioning
Parking available
Guest House Sanctuary by Evergreen Home
Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Free WiFi
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 barbecue grills and a fireplace in the lobby.
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
The price is $150 per night from May 6 to May 7
$150
includes taxes & fees
$134 per night
May 6 - May 7
9.2/10 Wonderful! (2,281 reviews)
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
The price is $115 per night from May 6 to May 7
$115
includes taxes & fees
$103 per night
May 6 - May 7
9/10 Wonderful! (577 reviews)
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
The price is $129 per night from May 8 to May 9
$129
includes taxes & fees
$114 per night
May 8 - May 9
8/10 Very Good! (1,285 reviews)
Chester Guest Houses essential information
Accommodation | 7 Guest Houses |
|---|---|
Lowest Price | $115 |
Highest Price | $269 |
Popular accommodation | The Central Downtown Inn & Suites, 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, Chestnut Lodge, Cliffwood Cottage by Evergreen Home |