Book Hotels in Chester, MD

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Top Chester hotels

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
$186 nightly
The price is $212 total per night from Oct 12 to Oct 13
$212 total
Oct 12 - Oct 13
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 free WiFi in public areas, conference space, ...
"What a great hotel. Navy themed. Great location."

Reviewed on Sep 17, 2025

Opens in a new windowGraduate 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
$101 nightly
The price is $115 total per night from Oct 14 to Oct 15
$115 total
Oct 14 - Oct 15
Total with 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 ...
"This was a convenient property for visiting the Naval Academy and historic Annapolis. The property seemed to be well taken care of. The breakfast was the usual breakfast area with a waffle maker, oatmeal, a hot serving dish of an egg product, a meat, and a potato product. Nothing fancy. The room ..."

Reviewed on Sep 22, 2025

Opens in a new windowCountry Inn & Suites by Radisson, Annapolis, MD
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
$155 nightly
The price is $176 total per night from Oct 27 to Oct 28
$176 total
Oct 27 - Oct 28
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. ...
"Nice and clean room in historical building. Next to state building in historic district of the town"

Reviewed on Sep 22, 2025

Opens in a new windowHistoric Inns of Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $121 total per night from Oct 1 to Oct 2
$121 total
Oct 1 - Oct 2
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. ...
"Nice location"

Reviewed on Sep 24, 2025

Opens in a new windowSonesta ES Suites Annapolis
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
$106 nightly
The price is $121 total per night from Sep 30 to Oct 1
$121 total
Sep 30 - Oct 1
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 business center and free WiFi in public areas. ...
McMullen Symposium
"Clean room, efficient staff and superb breakfast. Grateful thanks to the hotel staff."

Reviewed on Sep 21, 2025

Opens in a new windowDoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
$112 nightly
The price is $128 total per night from Oct 14 to Oct 15
$128 total
Oct 14 - Oct 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 business center and free WiFi in public areas. ...
Happy 34th Chris & Char
"My wife and were away to celebrate our 34th wedding anniversary and the stay was close to home affordable and very comfortable. Hotel staff was very friendly and welcoming"

Reviewed on Sep 20, 2025

Opens in a new windowCrowne Plaza Annapolis by IHG
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $244 total per night from Oct 26 to Oct 27
$244 total
Oct 26 - Oct 27
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this Beaux Arts hotel. Traveling on business? Take advantage of the 24-hour business ...
"Excellent hotel"

Reviewed on Sep 14, 2025

Opens in a new windowThe Westin Annapolis
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
$92 nightly
The price is $102 total per night from Oct 5 to Oct 6
$102 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of ...
"When it takes two tries to get the room key to"

Reviewed on Sep 16, 2025

Opens in a new windowSt Michaels Inn
Best Western Annapolis

Best Western Annapolis

2.5 out of 5
2520 Riva Rd, Annapolis, MD
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $94 total per night from Sep 30 to Oct 1
$94 total
Sep 30 - Oct 1
Total with 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 ...
"The only thing was the traffic noise from the parkway."

Reviewed on Sep 21, 2025

Opens in a new windowBest Western Annapolis
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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.

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 $94. 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 1,245 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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

5 out of 5
Posted 4 days ago
Travelocity Verified Review
" evering"
A verified traveler stayed at Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
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