Hotels in Kennedyville

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Check prices for these dates

Tonight
May 8 - May 9
Tomorrow
May 9 - May 10
This weekend
May 9 - May 11
Next weekend
May 16 - May 18

Where to stay in Kennedyville?

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (760)
The price is $122
includes taxes & fees
$110 per night
May 18 - May 19
Comfort Inn & Suites Chestertown
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.

Learn more about Kennedyville

Kennedyville is well-known for its attractions such as Crow Farm and Vineyard and Turner Creek Landing Park.

See all hotels in Kennedyville
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
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Frequently asked questions

What accommodations do travelers recommend in Kennedyville?
Guests like Red Roof Inn & Suites Chestertown.
Can I book refundable accommodations in Kennedyville?
If you’re looking for the flexibility to change your travel plans to Kennedyville, most properties provide refundable* rates you can book. You can see these properties by searching our site and using the “fully refundable” filter to narrow the results down.
What will the weather in Kennedyville be like during my visit?
July and August are typically the warmest months in Kennedyville when the average temp is 74°F. January and February are the coldest months when the average temperature is 39°F. August and July are the months with the most rain.
Why should I book my Kennedyville accommodation with Hotels.com?
There are lots of reasons to book your Kennedyville trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

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