Hotels in Chester

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Top 5 hotels in Chester at a glance

Laurel Grove Inn on the South — 3.5-star hotel in Annapolis. Guest rating: 9.2/10 — Wonderful.
Hyatt Place Kent Narrows & Marina — 3-star hotel in Grasonville. Guest rating: 9.4/10 — Exceptional.
Holiday Inn Express Annapolis East-Kent Island by IHG — 2.5-star hotel in Grasonville. Guest rating: 9.2/10 — Wonderful.
Hilton Garden Inn Kent Island Marina — 3-star hotel in Grasonville. Guest rating: 9.0/10 — Wonderful.
Best Western Kent Narrows Inn — 2.5-star hotel in Grasonville. Guest rating: 8.0/10 — Very Good.

Where to stay in Chester?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Chester on Hotels.com. These Chester hotels consistently deliver on comfort, location and traveler experience. Last updated on August 22, 2026.

Laurel Grove Inn on the South

Annapolis

CNY1,210

CNY1,379 total

includes taxes & fees

Sep 21 - Sep 22

Hyatt Place Kent Narrows & Marina

Grasonville

CNY1,123

CNY1,246 total

includes taxes & fees

Sep 8 - Sep 9

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

CNY854

CNY948 total

includes taxes & fees

Sep 1 - Sep 2

Hilton Garden Inn Kent Island Marina

Grasonville

CNY987

CNY1,095 total

includes taxes & fees

Sep 1 - Sep 2

Best Western Kent Narrows Inn

Grasonville

CNY855

CNY949 total

includes taxes & fees

Sep 1 - Sep 2

The Inn at Chesapeake Bay Beach Club

Stevensville

CNY1,583

CNY1,929 total

includes taxes & fees

Sep 20 - Sep 21

Kent Island Resort

Stevensville

CNY1,034

CNY1,376 total

includes taxes & fees

Sep 10 - Sep 11

Quality Inn Grasonville near Kent Island

Grasonville

CNY678

CNY752 total

includes taxes & fees

Sep 14 - Sep 15

SpringHill Suites by Marriott Annapolis

Annapolis

CNY867

CNY988 total

includes taxes & fees

Aug 30 - Aug 31

Suite, 1 King Bed, Non Smoking, Corner (with Sofabed)

Best Western Plus Easton Inn & Suites

Easton

CNY934

CNY1,028 total

includes taxes & fees

Sep 20 - Sep 21

Inn at Huntingfield Creek

Rock Hall

CNY1,213

CNY1,347 total

includes taxes & fees

Aug 23 - Aug 24

DoubleTree by Hilton Hotel Annapolis

Annapolis

CNY656

CNY748 total

includes taxes & fees

Aug 30 - Aug 31

Holiday Inn Express Easton by IHG

Easton

CNY1,069

CNY1,176 total

includes taxes & fees

Aug 23 - Aug 24

The Westin Annapolis

Annapolis

CNY1,137

CNY1,296 total

includes taxes & fees

Aug 30 - Aug 31

Historic Inns of Annapolis

Historic District

CNY623

CNY940 total

includes taxes & fees

Aug 30 - Aug 31

Room, 1 King Bed, Non Smoking, Fireplace

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

CNY640

CNY729 total

includes taxes & fees

Sep 16 - Sep 17

Courtyard by Marriott Annapolis

Annapolis

CNY619

CNY705 total

includes taxes & fees

Aug 30 - Aug 31

Fairfield Inn & Suites by Marriott Easton

Easton

CNY909

CNY1,000 total

includes taxes & fees

Aug 30 - Aug 31

Hilton Garden Inn Annapolis

Annapolis

CNY656

CNY748 total

includes taxes & fees

Sep 21 - Sep 22

Best Western Annapolis

Annapolis

CNY539

CNY614 total

includes taxes & fees

Aug 30 - Aug 31

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Go beyond your typical stay in Chester

Pet friendly

Pool

Family friendly

Hot tub

Top landmarks in Chester

Chesapeake Exploration Center

Chesapeake Exploration Center is worth a visit, located 0.8 mi (1.4 km) from central Kent Narrows.

See properties

Learn more about Chester

The region around Chester is home to attractions such as Chesapeake Exploration Center and Northern Chesapeake Bay.

See all hotels in Chester

A boat docked at a pier during twilight with a city skyline in the background.

Check out reviews of Chester hotels guests love

Historic Inns of Annapolis

10/10 Excellent

"Great location nicely appointed room, great paintings"

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Great staff everywhere on the property."

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"A"

Sonesta ES Suites Annapolis

10/10 Excellent

"I reserve two rooms for me and my family. We had an amazing time and the temperature was perfect. After being outside at the beach all day. The bathrooms were small but clean and the areas were all clean a lot of fresh tiles and wash rags and the bed was also clean breakfast in the morning was very nice. They had a pancake maker cereal, and there was something for everybody, including eggs and sausage I would definitely recommend and come again easy check-in process Miss D made everything enjoyable and check out with smooth as well."

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent

"Perfect for what I needed"

The Wildset

10/10 Excellent

"Stayed before and will stay again. Love it because of location, staff and food."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Rooms where clean, staff was nice"

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Top notch staff from the front desk, housekeeping and valet. My only real complaint was the early AM construction in the hallway. But all the workers were friendly and courteous to me passing by to get to the elevator."

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Property was well maintained and clean. Room was spacious and with a nice view. Parking is somewhat limited. Location is also central to area,attractions."

Frequently asked questions

How much does a hotel room cost in Chester?

You can find top hotels in Chester from CNY614 with options to suit your budget and needs. If you're after an affordable hotel in Chester that meets all of your requirements, set your filters and then sort the results by "Price: low to high".

How can I find deals and earn rewards at Chester hotels?

Discover great deals on Chester hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Chester hotels.

Can I book Chester hotels with free cancellation?

It's easy to book a refundable Chester hotel on Hotels.com. Simply filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some popular hotels in central Chester?

If you're looking for hotels in central Chester, check out Hyatt Place Kent Narrows & Marina and Hilton Garden Inn Kent Island Marina. Travelers love Hyatt Place Kent Narrows & Marina for its location, as well as the indoor pool, restaurant and bar/lounge this hotel offers. Hilton Garden Inn Kent Island Marina is another popular central hotel with an indoor pool, a restaurant and a bar/lounge.

What accommodations do travelers recommend in Chester?

Guests like Hyatt Place Kent Narrows & Marina, Holiday Inn Express Annapolis East-Kent Island by IHG and Hilton Garden Inn Kent Island Marina.

Can I book a refundable accommodation in Chester?

If you're looking for the flexibility to change your travel plans to Chester, most properties provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Chester if I want a vacation rental instead of a traditional hotel?

If you want to find a good alternative to a hotel, review our selection of 8 vacation homes.

What will the weather in Chester be like during my visit?

July and August are typically the warmest months in Chester when the average temp is 74°F. January and February are the coldest months when the average temperature is 39°F. July and October are the months with the most rain.

Why should I book my Chester hotel through Hotels.com?

There are lots of reasons to book your Chester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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