Compare Inns in Chester

Start date: Check-in selected.
To Date
End date: Check-out

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 Inns in Chester

Don't see what you're looking for?
See all available properties in Chester
View all properties
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

    D. Hotel Suites & Spa

    1 Country Club Rd Holyoke MA
    $134 nightly
    The price is $149 total per night from Jan 1 to Jan 2
    $149 total
    Jan 1 - Jan 2, 2026
    Total with taxes and fees
    9.2/10 Wonderful! (2,235 reviews)
    La Quinta Inn & Suites by Wyndham Springfield MA

    La Quinta Inn & Suites by Wyndham Springfield MA

    100 Congress Street Springfield MA
    $111 nightly
    The price is $125 total per night from Dec 29 to Dec 30
    $125 total
    Dec 29 - Dec 30
    Total with taxes and fees
    8/10 Very Good! (1,307 reviews)
    The Yankee, Trademark Collection by Wyndham

    The Yankee, Trademark Collection by Wyndham

    461 Pittsfield Rd Lenox MA
    $93 nightly
    The price is $103 total per night from Jan 4 to Jan 5
    $103 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    9/10 Wonderful! (1,006 reviews)

Inns

Find a great Chester inn
If you’re on the lookout for a place to stay in Chester that sports special touches and décor but is less costly than a bed and breakfast, rent a room at an inn. Whether you’re staying for a day, a week or a month, Orbitz has a great selection of super-comfy Chester inns to choose from.

Pick the right inn for you
The most popular hotel inns in Chester merge the convenience of an inn with many of the standard features of a hotel. Think pools and gyms, without the hefty price tag.

You’ll find Chester inns are located in all sort of convenient neighborhoods, making them a great option for those traveling on four wheels. They can also offer a tasty breakfast and hearty dinner, saving you the time and effort it would take to find good eats in a new place. 

If you want a space filled with loads of personality and a good helping of hospitality to boot, look out for historic inns. Privately owned with an exclusive number of rooms, you’ll receive a more personalized stay, much like a boutique hotel. No matter what type of inn you choose, you’re sure to enjoy unique experiences you won’t find anywhere else.

Chester Inns essential information

Accommodation
4 Inns
Lowest Price
$103
Highest Price
$368
Popular accommodation
Apple Tree Inn, The Old Inn On The Green, Kemble Inn, The Kemble Berkshires