Photo by Assya A

Hotels with Parking in Chestertown

Free cancellation options if plans change
Unlock travel rewards with One Key
Save more with Member Prices

Check prices for these dates

Tonight
Jun 29 - Jun 30
Tomorrow
Jun 30 - Jul 1
Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13

Hotels with Parking in Chestertown

The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (52)
$147 nightly
The price is $163
Jun 30 - Jul 1
Total includes taxes and fees
The Lodge at Great Oak Landing
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.

Top landmarks in Chestertown

Washington College

If you'd like to get a taste of Chestertown student life, check out Washington College, in the heart of the town.

See properties in Washington College
Washington College

Frequently asked questions

What are the best hotels with parking in Chestertown?
According to guest reviews, Comfort Inn & Suites Chestertown is one of the top Chestertown hotels with parking. It also has designer toiletries and a swimming pool. Another visitor favorite where you can drive up and check in is Red Roof Inn & Suites Chestertown. To find other popular options with on-site or free parking in Chestertown, select the "Parking" filter and then sort by "Guest rating + our picks."
What are the cheapest hotels with parking in Chestertown?
Find some of the cheapest hotels in Chestertown with parking for your next trip. Park your car at Comfort Inn & Suites Chestertown, which also offers a swimming pool and designer toiletries. Red Roof Inn & Suites Chestertown is another option that features parking in Chestertown and won't cost a fortune.
What is the best time to stay in a hotel with parking in Chestertown?
The best time to stay in a hotel with parking in Chestertown depends on your travel style. Go in peak season to experience everything in full swing, or choose a quieter time for smaller crowds and potentially more affordable hotels. Also consider the weather you prefer and the activities you're eager to do.
What hotels with parking are closest to Rolphs Wharf Marina?
Just a quick drive from Rolphs Wharf Marina, Comfort Inn & Suites Chestertown is one of the closest hotels with parking. Take advantage of a swimming pool and designer toiletries here. Another nearby option is Red Roof Inn & Suites Chestertown. Book a hotel in Chestertown with parking and come and go on your own terms.
Are there any hotels in Chestertown with free parking?
You'll find Chestertown hotels with parking. At Comfort Inn & Suites Chestertown, it's included in the price. This escape has a swimming pool and designer toiletries. Or, head to Red Roof Inn & Suites Chestertown, where parking is on the house as well.
Are all taxes and fees included in the Chestertown hotel prices shown on Hotels.com?
Hotels.com provide upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.