Book Hotels in Chester, 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

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility

Top Chester hotels

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $177 total per night from Aug 3 to Aug 4
$177 total
Aug 3 - Aug 4
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, ...
"Excellent!"

Reviewed on Jul 21, 2025

Graduate by Hilton Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
$97 nightly
The price is $110 total per night from Jul 31 to Aug 1
$110 total
Jul 31 - Aug 1
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot ...
"Nice stay. HVAC was quite noisy. Overall a nice stay & convenient to area attractions. Would stay again."

Reviewed on Jul 20, 2025

Country Inn & Suites by Radisson, Annapolis, MD
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $115 total per night from Aug 3 to Aug 4
$115 total
Aug 3 - Aug 4
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...
"There was nothing wrong with the place or room. Just a little surprised to have to pay an extra $10 a night for parking."

Reviewed on Jul 22, 2025

SpringHill Suites by Marriott Annapolis
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
$143 nightly
The price is $163 total per night from Aug 3 to Aug 4
$163 total
Aug 3 - Aug 4
Total includes 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. ...
"Overall it is a great hotel to stay, close to all activities"

Reviewed on Jul 23, 2025

Historic Inns of Annapolis
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
$220 nightly
The price is $251 total per night from Aug 17 to Aug 18
$251 total
Aug 17 - Aug 18
Total includes 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 ...
"The hotel offers a breathtaking view of the water. The room was clean, spacious, and comfortable. I found the staff to be attentive, friendly, and knowledgeable. They provided information regarding great places to eat and things to do. There is a wonderful yacht cruise that departs directly behind ..."

Reviewed on Jul 9, 2025

Annapolis Waterfront Hotel, Autograph Collection
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
$89 nightly
The price is $101 total per night from Jul 27 to Jul 28
$101 total
Jul 27 - Jul 28
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
"The hotel is convenient and location right off the highway. I like this hotel for the price and the mall.They have great food locations. Close to the marina. I didn't like was it was a large event that messed up the hotel. They were slamming the room doors after 10 pm. The TV kept freezing and the ..."

Reviewed on Jul 8, 2025

Crowne Plaza Annapolis by IHG
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $112 total per night from Aug 3 to Aug 4
$112 total
Aug 3 - Aug 4
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
"The staff was very attentive and helpful. The restaurant and bar in the hotel was a delight."

Reviewed on Jul 22, 2025

DoubleTree by Hilton Hotel Annapolis
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $130 total per night from Aug 11 to Aug 12
$130 total
Aug 11 - Aug 12
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and ...
"The hotel was very conveniently located and we walked everywhere. Dining options were available within a 10 minute walk. Parking was onsite and we never mover our car. Good place to enjoy Annapolis"

Reviewed on Jul 24, 2025

Hilton Garden Inn Annapolis Downtown
Best Western Annapolis

Best Western Annapolis

2.5 out of 5
2520 Riva Rd, Annapolis, MD
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $89 total per night from Jul 30 to Jul 31
$89 total
Jul 30 - Jul 31
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the ...
"Clean and very nice staff"

Reviewed on Jul 19, 2025

Best Western Annapolis
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.

Chester Hotel & Travel Guide\n

If you are traveling about in Annapolis and feel like having a look around in Chester, there are a select variety of lodgings. Travelocity's travel guide presently lists 6 places to stay in and around the city center.

Learn about a few accommodation options that are within a short drive of Chester's urban center, such as the Historic Kent Manor Inn and Hilton Garden Inn Kent Island.

Have a look at the Inn at Perry Cabin by Belmond and also the Annapolis Waterfront Hotel, Autograph Collection. The Inn at Perry Cabin by Belmond is positioned 13 miles (21 kilometers) outside of the heart of Chester. The Annapolis Waterfront Hotel, Autograph Collection, is located just 11 miles (18 kilometers) away. Another possibility is to take a room at the Five Gables Inn and Spa or the Loews Annapolis Hotel.

If you have some spare time, you should travel further in the Central Maryland region. Central Maryland offers coastal plains, and other interesting tourist sites include street art. In this area of United States of America adventurous travelers may partake in shore fishing.

The nearest accommodations in Annapolis include Bowie and Arnold. Bowie is 25 miles (41 kilometers) to the west of Chester, while Arnold is 13 miles (20 kilometers) to the west. Bowie Travelocity-listed accommodations include the TownePlace Suites Bowie Town Center and Comfort Inn Conference Center. The Comfort Inn Annapolis and Village Inn are amongst the hotel establishments in Arnold.

Simply because you and your traveling partners are having a getaway, who's to say you shouldn't expand your passion for a day of sports. You will find Nationals Park 40 miles (64 kilometers) to the west of Chester. Those that wish to stay nearby can explore the The Jefferson, Washington, DC or the Marriott Marquis Washington, DC.

Baltimore Washington International Thurgood Marshall Airport is a practical entry point for accessing Chester. You can find it 25 miles (41 kilometers) from the downtown area. For travelers who would find it convenient to stay nearby, book the Residence Inn by Marriott Baltimore BWI Airport or BWI Airport Marriott.

Frequently asked questions

What are the top kid-friendly hotels in Chester?
Family vacations are where treasured memories are made, but it's no secret that traveling with children can be daunting. These kid-friendly Chester hotels come with perks that aim to keep adventurers of all ages comfortable and happy: The whole gang will love staying at New! Stylish downtown home w/awesome outdoor area!. A nearby beach and free WiFi are just a couple of the things that help make this place a winner. Also look into Bentons Pleasure- Cox Creek, Pier and Sunsets!. It comes with a playground, a king bed and lots of opportunities to spend time together.
Where can I find cheap hotels in Chester?
At Travelocity you'll find really nice hotels in Chester 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 Chester rather than in Chester. We may find you even better rates, too.
How do I find the best Chester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chester 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 Chester?
The cheapest hotel in Chester is $89. 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 Chester?
There are 1,241 hotels in Chester on Travelocity.
What are the best hotels in Chester?
Chester 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 Chester for you!
When is the best time to visit Chester?
If you want the joy of a fun-filled trip in peak season, visit Chester during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Chester?
Based on historic data is usually the cheapest month to visit Chester. 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 Chester?
There are multiple hotels in Chester 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 Chester. We have plenty of kid-friendly hotels in Chester to choose from on Travelocity!
Why book a hotel in Chester through Travelocity?
Because we have the top hotels in Chester! 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 Chester 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 Chester hotel reviews by fellow wanderers

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

5 out of 5
Posted 3 hours ago
Travelocity Verified Review
"The hotel was very conveniently located and we walked everywhere. Dining options were available within a 10 minute walk. Parking was onsite and we never mover our car. Good place to enjoy Annapolis"
A verified traveler stayed at Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
Explore More Ways to Travel with Travelocity

Explore More Ways to Travel with Travelocity