Hotels in Chester

Q: What accommodations do travelers recommend in Chester?

Guests like Hyatt Place Kent Narrows & Marina , Best Western Kent Narrows Inn and The Inn at Chesapeake Bay Beach Club .

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Dates

March 2026

April 2026

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Where to stay in Chester?

Best Western Kent Narrows Inn

Grasonville

Waterfront hotel with stunning sunset views and indoor pool near hiking trails.

CNY714 total

includes taxes & fees

Mar 3 - Mar 4

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Escape to scenic Kent Island where bay views and bike trails await your morning coffee.

CNY859 total

includes taxes & fees

Mar 2 - Mar 3

Hilton Garden Inn Kent Island Marina

Grasonville

Waterfront hotel with an indoor pool, where stunning bay views greet you every day.

CNY804 total

includes taxes & fees

Mar 4 - Mar 5

Hyatt Place Kent Narrows & Marina

Grasonville

Unwind along the Eastern Shore with waterfront views and indoor pool access.

CNY836 total

includes taxes & fees

Mar 16 - Mar 17

The Inn at Chesapeake Bay Beach Club

Stevensville

Experience luxury seaside charm at this boutique spa hotel in Stevensville.

CNY1,438 total

includes taxes & fees

Mar 1 - Mar 2

Quality Inn Grasonville near Kent Island

Grasonville

A peaceful stay near Chesapeake Bay with free breakfast and outdoor pool.

CNY712 total

includes taxes & fees

Mar 9 - Mar 10

Inn at Huntingfield Creek

Rock Hall

Serene B&B on Chesapeake Bay offers outdoor pool and spa treatments in Rock Hall.

134 Prince - Luxury Boutique Hotel

Annapolis

Experience historic charm in Maryland's capital just steps from the U.S. Naval Academy.

Flag House Inn

Historic District

Experience historic charm in the heart of Annapolis near the U.S. Naval Academy.

CNY1,362 total

includes taxes & fees

Mar 1 - Mar 2

Fairfield Inn & Suites By Marriott Annapolis

Annapolis

Stay near U.S. Naval Academy with free breakfast and 24-hour fitness center.

CNY858 total

includes taxes & fees

Mar 5 - Mar 6

Hilton Garden Inn Annapolis Downtown

Annapolis

Centrally located hotel near U.S. Naval Academy with Art Deco design and fitness.

CNY728 total

includes taxes & fees

Mar 2 - Mar 3

Residence Inn By Marriott Annapolis

Annapolis

Enjoy a convenient stay near the Naval Academy with free breakfast daily.

CNY993 total

includes taxes & fees

Mar 8 - Mar 9

The Westin Annapolis

Annapolis

Luxurious spa escape near U.S. Naval Academy with attentive service.

CNY1,397 total

includes taxes & fees

Mar 1 - Mar 2

Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Historic District

Savor the harbor views and rooftop terrace in walkable downtown Annapolis.

CNY1,386 total

includes taxes & fees

Mar 22 - Mar 23

George Brooks House B&B

St. Michaels

Victorian charm just steps from St. Michaels attractions with outdoor pool.

CNY1,273 total

includes taxes & fees

Mar 2 - Mar 3

Graduate by Hilton Annapolis

Annapolis

Relaxing retreat minutes from U.S. Naval Academy with on-site Trophy Room dining.

CNY1,219 total

includes taxes & fees

Mar 8 - Mar 9

Historic Inns of Annapolis

Historic District

Downtown charm steps from the U.S. Naval Academy in historic Annapolis.

Parsonage Inn

Downtown St. Michaels

Stay in a charming B&B in St. Michaels, with free breakfast and nearby trails.

CNY1,122 total

includes taxes & fees

Mar 31 - Apr 1

The Wildset

Downtown St. Michaels

Experience downtown St. Michaels with free breakfast, WiFi, and marina views.

CNY1,499 total

includes taxes & fees

Mar 1 - Mar 2

Premium bedding, down comforters, in-room safe, desk

Inn at Perry Cabin

Downtown St. Michaels

Classic Chesapeake Bay escape with marina, spa, and waterfront dining options.

CNY2,797 total

includes taxes & fees

Mar 4 - Mar 5

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Go beyond your typical stay in Chester

Family friendly

Spa

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.

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Learn more about Chester

The region around Chester is home to attractions such as Chesapeake Exploration Center and Paul Reed Smith Guitars.

See all hotels in Chester

Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.

Check out reviews of Chester hotels guests love

Best Western Kent Narrows Inn

10/10 Excellent

"Clean room, hot water, huge breakfast, indoor pool, definitely an inexpensive nice place to stay just over the Bay on Na Shore, walking distance to Kent Narrows Airport "

Frequently asked questions

How much does a hotel room cost in Chester?

You can find top hotels in Chester from CNY712 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, Best Western Kent Narrows Inn and The Inn at Chesapeake Bay Beach Club.

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 10 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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