Compare Chester Guest House Rentals
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Guest Houses in Chester
The Central Downtown Inn & Suites
20 W Housatonic St., Pittsfield, MA
$119 nightly
The price is $133 total per night
$133 total
Jul 16 - Jul 17
Total includes 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
The Dewey
7 Hubbard Street, Lenox, MA
$202 nightly
The price is $226 total per night
$226 total
Jul 15 - Jul 16
Total includes taxes and fees
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
Berkshire Village Carriage House - Super Private!!
$262 nightly
The price is $293 total per night
$293 total
Jul 31 - Aug 1
Total includes taxes and fees
Guests staying at this vacation home have access to 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
Jul 14 - Jul 15
Total includes 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
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 fireplace in the lobby. You can take advantage of free parking if you drive. Additional amenities include barbecue grills and a picnic area.
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
Quality Inn West Springfield
1150 Riverdale St, West Springfield, MA
$89 nightly
The price is $102 total per night from Jul 13 to Jul 14
$102 total
Jul 13 - Jul 14
Total includes taxes and fees
7/10 Good! (1,001 reviews)
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
$79 nightly
The price is $88 total per night from Jul 6 to Jul 7
$88 total
Jul 6 - Jul 7
Total includes taxes and fees
5.4/10 (733 reviews)
La Quinta Inn & Suites by Wyndham Springfield MA
100 Congress Street, Springfield, MA
$114 nightly
The price is $129 total per night from Jul 8 to Jul 9
$129 total
Jul 8 - Jul 9
Total includes taxes and fees
8/10 Very Good! (1,269 reviews)
Chester Guest Houses essential information
Accommodation | 9 Guest Houses |
|---|---|
Lowest Price | $88 |
Highest Price | $293 |
Popular accommodation | The Central Downtown Inn & Suites, The Dewey, Berkshire Village Carriage House - Super Private!!, A European Country Getaway ~ 1930s Stone Cottage In Connecticut!, Guest House Sanctuary by Evergreen Home, Jacob's Tanglewood Ranch, Cliffwood Cottage by Evergreen Home, Chestnut Lodge |