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
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $173 total per night from Jan 19 to Jan 20
$173 total
Jan 19 - Jan 20, 2026
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, ...
Room was spotless. The staff was helpful

Reviewed on Dec 16, 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
$94 nightly
The price is $107 total per night from Jan 5 to Jan 6
$107 total
Jan 5 - Jan 6, 2026
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 ...
It was clean, quiet and comfortable. Will definitely come back if in the area again.

Reviewed on Dec 17, 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
$169 nightly
The price is $193 total per night from Jan 1 to Jan 2
$193 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. ...
Best place to stay is the main building

Reviewed on Dec 22, 2025

Opens in a new windowHistoric 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 Jan 11 to Jan 12
$251 total
Jan 11 - Jan 12, 2026
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 ...
THE ROOM WAS CLEAN AND BEDS WERE COMFORTABLE THE STAFF WAS FRIENDLY THE LOCATION WAS PERFECT I WOULD STAY THERE AGAIN ON BAD THING THE COFFEE MACHINE AND THE COFFEE WERE BAD SWITCH TO A BETTER COFFEE

Reviewed on Dec 27, 2025

Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis

3 out of 5
200 Taylor Avenue Annapolis MD
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $125 total per night from Jan 4 to Jan 5
$125 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free full breakfast each ...
Beautiful hotel, clean, very comfortable bed, delicious breakfast. The only negative thing is the $30 parking- not even valet- it’s kind of ridiculous when they have their own dedicated lot. It’s kind of a racket. Everything else was top notch, though!

Reviewed on Dec 21, 2025

Opens in a new windowFairfield Inn & Suites By Marriott 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
$75 nightly
The price is $85 total per night from Jan 4 to Jan 5
$85 total
Jan 4 - Jan 5, 2026
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. ...
did not dine in your hotel.

Reviewed on Dec 24, 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
$110 nightly
The price is $125 total per night from Jan 3 to Jan 4
$125 total
Jan 3 - Jan 4, 2026
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. ...
Everything was good - only minor negatives: 1) bathroom sink drained verrrrrry slowly 20-30 min to drain the sink completely. 2) bedding had an odd smell, though it didn’t seem unclean. 3) the tub has a significant slope to the center, which is scary; when it’s wet, especially when there’s soap residue; ...

Reviewed on Dec 27, 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
$139 nightly
The price is $158 total per night from Jan 1 to Jan 2
$158 total
Jan 1 - Jan 2, 2026
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 ...
Beautiful and perfect location

Reviewed on Dec 22, 2025

Opens in a new windowThe Westin 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
$84 nightly
The price is $96 total per night from Jan 13 to Jan 14
$96 total
Jan 13 - Jan 14, 2026
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, free WiFi in public areas, and ...
Excellent

Reviewed on Dec 27, 2025

Opens in a new windowHilton Garden Inn Annapolis Downtown
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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 $85. 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 1,192 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 days ago
Travelocity Verified Review
"Excellent"
A verified traveler stayed at Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown

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