Book Hotels in Chestertown, MD

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Cheap Chestertown hotels

Driftwood Inn

609 Washington Avenue, Chestertown, MD

5/10 (174 reviews)

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.

Chestertown Hotel & Travel Guide\n

For those adventurers that find themselves roaming around in Eastern Chesapeake Shore and decide on spending some time in Chestertown, there are a select number of hotels. With 5 accommodation options on Travelocity within a 6-mile (10-kilometer) sweep of Chestertown, it'll be easy finding something that ticks all your boxes.

Chestertown's downtown region is within strolling distance of comfortable hotels including Holiday Inn Express Hotel & Suites Chestertown and Quality Suites.

Chestertown features just a handful of no-frills hotels; you'll find the Driftwood Inn located 2 miles (3 kilometers) from the heart of town.

Check out the Historic Kent Manor Inn and also the Hilton Garden Inn Kent Island. The Historic Kent Manor Inn is located 20 miles (32 kilometers) away from the center of Chestertown. The Hilton Garden Inn Kent Island, is located 18 miles (29 kilometers) away. Some other accommodation options include the Best Western Kent Narrows Inn and the Holiday Inn Express Annapolis - Kent Island.

Keen on exploring more of the coastal plains and wetlands that this area features? How about you have a few nights in some of the other places in Eastern Maryland? No matter if you get involved with commonplace local activities, like, for example, ice fishing, hiking and shore fishing, or desire to zigzag across the region to photograph the many attractions, you will have no trouble booking comfortable Travelocity-listed hotels close to here.

Looking for more things to do? You could spend a few hours seeing Chesapeake Bay Maritime Museum and St. Michaels Museum, which you'll find in St. Michaels, 30 miles (47 kilometers) south of Chestertown. If you head to St. Michaels, check out the Inn at Perry Cabin by Belmond and Five Gables Inn and Spa. For another option, head to Rock Hall, 10 miles (16 kilometers) to the southwest of Chestertown, where you can pick from the Mariners Motel and Inn at Osprey Point. When you visit Rock Hall, be sure to venture to the Mainstay and Rock Hall Harbor.

Baltimore Washington International Thurgood Marshall Airport is 30 miles (50 kilometers) away from the center of Chestertown. Enlightened visitors who need to find a room nearby can easily secure a convenient option in the Residence Inn by Marriott Baltimore BWI Airport or the BWI Airport Marriott.

Frequently asked questions

What are the top kid-friendly hotels in Chestertown?

From cool amenities to more room to move, kid-friendly hotels are equipped with features that can help transform an everyday family vacation into an extraordinary one. These Chestertown options make getting away with the youngsters a snap: The whole team will enjoy their time at Driftwood Inn. Pet-friendly facilities and front desk services are just a few of the things that help make this property a sought-after option. Carriage House Hideaway in Middle of Chestertown is another excellent choice. After a fun day of exploring, return to your cozy room and perks like a playground and animal viewing activities.

Where can I find cheap hotels in Chestertown?

At Travelocity you'll find really nice hotels in Chestertown at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chestertown rather than in Chestertown. We may find you even better rates, too.

How do I find the best Chestertown hotel deals?

Simple! On Travelocity, look through the fantastic offers we've already found in Chestertown then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.

How much does it cost to stay in a hotel in Chestertown?

The cheapest hotel in Chestertown is $71. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.

How many hotels are in Chestertown?

There are 1,081 hotels in Chestertown on Travelocity.

What are the best hotels in Chestertown?

Chestertown has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chestertown for you!

When is the best time to visit Chestertown?

If you want the joy of a fun-filled trip in peak season, visit Chestertown during February, March and October. If you'd prefer the peace of off-season, book a stay during quieter months, such as May, November and December.

When is the cheapest time to stay in Chestertown?

Based on historic data is usually the cheapest month to visit Chestertown. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.

Are there any great family-friendly hotels in Chestertown?

There are multiple hotels in Chestertown that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chestertown. We have plenty of kid-friendly hotels in Chestertown to choose from on Travelocity!

Why book a hotel in Chestertown through Travelocity?

Because we have the top hotels in Chestertown! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!

How do I cancel my hotel booking in Chestertown on Travelocity?

Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chestertown hotel reviews by fellow wanderers

Historic Inns of Annapolis

5 out of 5

Posted 18 hours ago

Travelocity Verified Review

"The only criticism I have is that the towels were in terrible condition and even stained"

A verified traveler stayed at Historic Inns of Annapolis

Courtyard by Marriott Baltimore Downtown/McHenry Row

5 out of 5

Posted 6 days ago

Travelocity Verified Review

"Clean room easy access from the interstate after a long day of driving. We were able to walk to fort McHenry, to stretch the legs after a 14 hour drive. Safe parking, quiet room with a comfy bed. No complaints. "

A verified traveler stayed at Courtyard by Marriott Baltimore Downtown/McHenry Row