Photo by Patricia Knorr

Find hotels in Chester, MD from CA $114

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Compare 1,239 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (881)
"Great stay beautiful view"
The price is CA $175
CA $194 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Annapolis East-Kent Island by IHG

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (604)
"Great place to stay. "
The price is CA $219
CA $243 total
includes taxes & fees
Aug 21 - Aug 22
Hyatt Place Kent Narrows & Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (982)
"Friendly staff, nice environment"
The price is CA $210
CA $233 total
includes taxes & fees
Sep 1 - Sep 2
Hilton Garden Inn Kent Island Marina

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1006)
"The Hotel was very clean and convenient to everything that we wanted to do!!!!"
The price is CA $219
CA $250 total
includes taxes & fees
Aug 24 - Aug 25
The Westin Annapolis

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very good, (1006)
"Such friendly staff"
The price is CA $131
CA $150 total
includes taxes & fees
Aug 18 - Aug 19
Hilton Garden Inn Annapolis

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1000)
"Great place and great staff "
The price is CA $145
CA $165 total
includes taxes & fees
Aug 19 - Aug 20
Courtyard by Marriott Annapolis

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (854)
" Very clean, spacious room, friendly staff"
The price is CA $327
CA $372 total
includes taxes & fees
Aug 24 - Aug 25
Annapolis Waterfront Hotel, Autograph Collection

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1832)
"Great stay"
The price is CA $140
CA $207 total
includes taxes & fees
Aug 19 - Aug 20
Historic Inns of Annapolis

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very good, (1008)
"Very nice stay. Front desk staff was friendly and the pool is a great bonus."
The price is CA $138
CA $158 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn & Suites Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1009)
"Great visit "
The price is CA $134
CA $152 total
includes taxes & fees
Aug 21 - Aug 22
Country Inn & Suites by Radisson, Annapolis, MD

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (408)
"Great location and amenities"
The price is CA $282
CA $349 total
includes taxes & fees
Aug 24 - Aug 25
The Inn at Chesapeake Bay Beach Club

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (59)
"Good service and good options to enjoy the stays. "
The price is CA $236
CA $320 total
includes taxes & fees
Aug 24 - Aug 25
Wylder Tilghman Island

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (107)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is CA $234
CA $311 total
includes taxes & fees
Sep 1 - Sep 2
Kent Island Resort

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1001)
"Bed was great"
The price is CA $134
CA $152 total
includes taxes & fees
Aug 18 - Aug 19
Holiday Inn Express & Suites Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1004)
"The Double Tree was a great place to stay! Great location amd the staff are very pleasant and helpful! "
The price is CA $138
CA $158 total
includes taxes & fees
Aug 20 - Aug 21
DoubleTree by Hilton Hotel Annapolis

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Great place"
The price is CA $145
CA $166 total
includes taxes & fees
Aug 18 - Aug 19
SpringHill Suites by Marriott Annapolis

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1008)
"Nice spot in a convenient but quiet area. "
The price is CA $154
CA $176 total
includes taxes & fees
Aug 28 - Aug 29
Crowne Plaza Annapolis by IHG

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (853)
"Great room for a great price... Very friendly staff, too."
The price is CA $131
CA $149 total
includes taxes & fees
Sep 2 - Sep 3
Sonesta ES Suites Annapolis

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (101)
"Beautiful location on the water. The staff are super nice and helpful. The restaurant is very good. We had an excellent house smoked pulled pork sandwich and a shrimp po boy."
The price is CA $282
CA $311 total
includes taxes & fees
Aug 24 - Aug 25
The Tilghman Island Inn

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (133)
"complimentry breakfast is good ,friendly staff,clean and quite "
The price is CA $175
CA $199 total
includes taxes & fees
Aug 24 - Aug 25
Fairfield Inn & Suites By Marriott Annapolis
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.
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Learn more about Chester

Chester awaits: its island views, sunny weather, golf, and more!

Photo by Patricia Knorr
Open Photo by Patricia Knorr

Stay near popular Chester attractions

Chesapeake Exploration Center

Chesapeake Exploration Center

Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.

Frequently asked questions

What's the best place to stay in Chester?

Located 10.8 mi (17.3 km) from the heart of Chester, Historic Inns of Annapolis is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Graduate by Hilton Annapolis and Country Inn & Suites by Radisson, Annapolis, MD. See all available top hotels, or vacation rentals in Chester.

What's the top vacation rental in Chester?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: Visitors like this Chester vacation home rental. It offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. See all vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes! You'll find that most hotel room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

Where can I learn more about changing or cancelling my trip to Chester?

To find more details about rescheduling or cancelling your trip to Chester, head over to our customer service page.

What are some accommodations with pools in Chester?

Country Inn & Suites by Radisson, Annapolis, MD: Provides buffet, an indoor pool, and free self parking. Sonesta ES Suites Annapolis and SpringHill Suites by Marriott Annapolis are a couple of other choices with an onsite pool. View all hotels with pools in Chester.

What is staying in Chester like?

Visitors can enjoy all that Chester has to offer including the waterfront, seafood restaurants, and golf courses. In Chester, there are 17 hotels and other accommodations to choose from. Find out more about Chester.

What is there to see in Chester?

Places to visit in the wider area include Matapeake State Park, Chesapeake Bay Environmental Center, and Love Point State Park. You'll also find Eastern Neck National Wildlife Refuge and Sandy Point Beach in the area. Check out what more to see and do in Expedia's Chester guide.

What's the weather like in Chester?

The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches.