Hotels in Chester

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Check prices for these dates

Tonight
Mar 25 - Mar 26
Tomorrow
Mar 26 - Mar 27
This weekend
Mar 27 - Mar 29
Next weekend
Apr 3 - Apr 5

Where to stay in Chester?

Reception
Kent Island Resort
Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (134 reviews)
The price is $104
$145 total
includes taxes & fees
Mar 26 - Mar 27
Kent Island Resort
Indoor pool
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Waterfront hotel with stunning sunset views and indoor pool near hiking trails.
The price is $101
$112 total
includes taxes & fees
Mar 31 - Apr 1
Best Western Kent Narrows Inn
Terrace/patio
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Waterfront hotel with an indoor pool, where stunning bay views greet you every day.
The price is $139
$154 total
includes taxes & fees
Mar 29 - Mar 30
Hilton Garden Inn Kent Island Marina
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (442 reviews)
  • cleanliness
    Experience luxury seaside charm at this boutique spa hotel in Stevensville.
The price is $166
$210 total
includes taxes & fees
Mar 30 - Mar 31
The Inn at Chesapeake Bay Beach Club
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (974 reviews)
  • cleanliness
    Escape to scenic Kent Island where bay views and bike trails await your morning coffee.
The price is $118
$131 total
includes taxes & fees
Apr 19 - Apr 20
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (727 reviews)
  • cleanliness
    Unwind along the Eastern Shore with waterfront views and indoor pool access.
The price is $151
$168 total
includes taxes & fees
Apr 14 - Apr 15
Hyatt Place Kent Narrows & Marina
Lobby
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (884 reviews)
  • cleanliness
    A peaceful stay near Chesapeake Bay with free breakfast and outdoor pool.
The price is $93
$104 total
includes taxes & fees
Mar 29 - Mar 30
Quality Inn Grasonville near Kent Island
Lake
Inn at Huntingfield Creek
Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
  • cleanliness
    Serene B&B on Chesapeake Bay offers outdoor pool and spa treatments in Rock Hall.
The price is $156
$173 total
includes taxes & fees
Mar 26 - Mar 27
Inn at Huntingfield Creek
Exterior
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (34 reviews)
  • cleanliness
    Experience historic charm in Maryland's capital just steps from the U.S. Naval Academy.
The price is $185
$211 total
includes taxes & fees
Mar 30 - Mar 31
134 Prince - Luxury Boutique Hotel
Lobby lounge
Flag House Inn
Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (89 reviews)
  • cleanliness
    Experience historic charm in the heart of Annapolis near the U.S. Naval Academy.
The price is $182
$207 total
includes taxes & fees
Mar 29 - Mar 30
Flag House Inn
Terrace/patio
Inn at Horn Point
Inn at Horn Point
3.0 star property
Eastport
9.6 out of 10, Exceptional, (21 reviews)
  • cleanliness
    Elegant colonial B&B near Annapolis Maritime Museum with a garden terrace.
The price is $524
$597 total
includes taxes & fees
Apr 9 - Apr 10
Inn at Horn Point
Meeting facility
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,875 reviews)
  • cleanliness
    Downtown charm steps from the U.S. Naval Academy in historic Annapolis.
The price is $127
$179 total
includes taxes & fees
Apr 2 - Apr 3
Historic Inns of Annapolis
Restaurant
Haven Point Inn and Gallery
Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is $155
$172 total
includes taxes & fees
Apr 21 - Apr 22
Haven Point Inn and Gallery
Property amenity
The Westin Annapolis
The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Luxurious spa escape near U.S. Naval Academy with attentive service.
The price is $179
$204 total
includes taxes & fees
Mar 27 - Mar 28
The Westin Annapolis
Terrace/patio
Fairfield Inn & Suites By Marriott Annapolis
Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (184 reviews)
  • cleanliness
    Stay near U.S. Naval Academy with free breakfast and 24-hour fitness center.
The price is $110
$125 total
includes taxes & fees
Apr 5 - Apr 6
Fairfield Inn & Suites By Marriott Annapolis
Lobby
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,007 reviews)
  • cleanliness
    Centrally located hotel near U.S. Naval Academy with Art Deco design and fitness.
The price is $105
$120 total
includes taxes & fees
Mar 29 - Mar 30
Hilton Garden Inn Annapolis Downtown
Terrace/patio
Residence Inn By Marriott Annapolis
Residence Inn By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (69 reviews)
  • cleanliness
    Enjoy a convenient stay near the Naval Academy with free breakfast daily.
The price is $135
$154 total
includes taxes & fees
Apr 5 - Apr 6
Residence Inn By Marriott Annapolis
Exterior
George Brooks House B&B
George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (70 reviews)
  • cleanliness
    Victorian charm just steps from St. Michaels attractions with outdoor pool.
The price is $160
$176 total
includes taxes & fees
Mar 26 - Mar 27
George Brooks House B&B
Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (912 reviews)
  • cleanliness
    Savor the harbor views and rooftop terrace in walkable downtown Annapolis.
The price is $212
$241 total
includes taxes & fees
Apr 12 - Apr 13
Annapolis Waterfront Hotel, Autograph Collection
Lobby
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,001 reviews)
  • cleanliness
    Relaxing retreat minutes from U.S. Naval Academy with on-site Trophy Room dining.
The price is $178
$203 total
includes taxes & fees
Apr 5 - Apr 6
Graduate by Hilton 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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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 Northern Chesapeake Bay.

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.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Check out reviews of Chester hotels guests love

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"."
Kirk 1-night trip
Posted 6 hours ago
Hyatt Place Kent Narrows & Marina

Frequently asked questions

What accommodations do travelers recommend in Chester?
Guests like Best Western Kent Narrows Inn, Hyatt Place Kent Narrows & Marina 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.