Book Hotels in Chestertown, MD

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Top Chestertown hotels

Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Fully refundableReserve now, pay when you stay
$355 nightly
The price is $417 total per night from Dec 23 to Dec 24
$417 total
Dec 23 - Dec 24
Total with taxes and fees
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...
Beautiful hotel. 5 out of 5

Reviewed on Dec 3, 2025

Opens in a new windowPendry Baltimore
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $203 total per night from Dec 14 to Dec 15
$203 total
Dec 14 - Dec 15
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
clean and great location

Reviewed on Nov 27, 2025

Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $164 total per night from Jan 1 to Jan 2
$164 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. ...
Upon entering the entire stay was a 10. The valet, seperate, were very courteous. The front desk staff were friendly and extremely helpful. The hotel was decorated for Christmas and was very festive. The room was clean and very roomy. The location could not have been better, directly across from ...

Reviewed on Dec 3, 2025

Opens in a new windowHistoric Inns of Annapolis
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $113 total per night from Dec 25 to Dec 26
$113 total
Dec 25 - Dec 26
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...
Excellent hotel. Will stay there anytime I travel to the area.

Reviewed on Nov 26, 2025

Opens in a new windowComfort Inn & Suites Chestertown
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 out of 5
6617 Ritchie Hwy Glen Burnie MD
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $105 total per night from Dec 15 to Dec 16
$105 total
Dec 15 - Dec 16
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of ...
Cle

Reviewed on Nov 9, 2025

Opens in a new windowHampton Inn Baltimore/Glen Burnie
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
$113 nightly
The price is $126 total per night from Dec 8 to Dec 9
$126 total
Dec 8 - Dec 9
Total with taxes and fees
A golf course, a 24-hour gym, and a restaurant are all featured at this smoke-free lodge. Relax with a drink at one of the 3 bars/lounges and enjoy free perks ...
Beautiful view

Reviewed on Nov 8, 2025

Opens in a new windowThe Lodge at Great Oak Landing
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street Baltimore MD
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Dec 14 to Dec 15
$105 total
Dec 14 - Dec 15
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
Great customer service

Reviewed on Dec 5, 2025

Opens in a new windowBest Western Plus Hotel & Conference Center
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard Baltimore MD
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $110 total per night from Dec 21 to Dec 22
$110 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the mini golf and barbecue grills. Enjoy the 24-hour gym and perks ...
The staff was so friendly, from check in, security, kitchen staff and all. The room was very clean. Breakfast was great! Mrs Cindy was so nice and you can tell she enjoys her job.

Reviewed on Dec 2, 2025

Opens in a new windowHilton Garden Inn Baltimore/White Marsh
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Dec 13 to Dec 14
$80 total
Dec 13 - Dec 14
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A lobby fireplace, laundry facilities, and free newspapers are also on ...
Professional staff, warm greetings clean room

Reviewed on Dec 1, 2025

Opens in a new windowRed Roof Inn & Suites Chestertown
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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.

Cheap Chestertown hotels

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 $70. 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 1,085 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.

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