Find hotels in Chester, MD from CA $118

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Our top choices for Chester hotels

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,002 reviews)
"Front desk staff were courteous and helpful. Breakfast was nice. I would stay again."
United States
Michael
The price is CA $149
CA $164 total
includes taxes & fees
Apr 28 - Apr 29
Best Western Plus Easton Inn & Suites

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (860 reviews)
"Room was clean and staff was friendly and helpful."
United States
Constantine
The price is CA $123
CA $136 total
includes taxes & fees
Apr 30 - May 1
Quality Inn

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, (996 reviews)
"Very nice hotel, good breakfast selection, clean rooms."
United States
Linda
The price is CA $183
CA $203 total
includes taxes & fees
May 4 - May 5
Holiday Inn Express Annapolis East-Kent Island by IHG

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (899 reviews)
"Breakfast menu had a great variety and was fresh. "
United States
Timothy
The price is CA $145
CA $161 total
includes taxes & fees
May 26 - May 27
Quality Inn Grasonville near Kent Island

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (482 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is CA $208
CA $237 total
includes taxes & fees
Apr 28 - Apr 29
Anchored Inn at Hidden Harbour Marina

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is CA $150
CA $166 total
includes taxes & fees
May 11 - May 12
Best Western Kent Narrows Inn

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (94 reviews)
"Very relaxing stay."
United States
Anne
The price is CA $284
CA $372 total
includes taxes & fees
May 11 - May 12
Wylder Tilghman Island

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
"Very nice room and wonderful stay."
United States
Julie
The price is CA $229
CA $301 total
includes taxes & fees
Apr 30 - May 1
Kent Island Resort

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is CA $205
CA $228 total
includes taxes & fees
May 13 - May 14
Haven Point Inn and Gallery

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 reviews)
"Beautiful area"
United States
Dan
The price is CA $217
CA $241 total
includes taxes & fees
Apr 28 - Apr 29
Hilton Garden Inn Kent Island Marina

Econo Lodge Easton Route 50

Econo Lodge Easton Route 50
2.5 star property
Easton
6.6 out of 10, (391 reviews)
"The parking was good but l didn't do breakfast "
United States
Tammy
The price is CA $123
CA $135 total
includes taxes & fees
Apr 28 - Apr 29
Econo Lodge Easton Route 50

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,004 reviews)
" Great place,great location, was in town for St Michael Chocolate fest "
United States
Katherine
The price is CA $185
CA $203 total
includes taxes & fees
May 4 - May 5
St Michaels Inn

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (602 reviews)
"Very nice stay"
United States
Nataliya
The price is CA $205
CA $226 total
includes taxes & fees
May 19 - May 20
Holiday Inn Express Easton by IHG

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (872 reviews)
"Enjoyable stay great location!"
United States
Michelle
The price is CA $231
CA $254 total
includes taxes & fees
May 3 - May 4
The Tidewater Inn

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (231 reviews)
"Great stay "
United States
Hani
The price is CA $144
CA $170 total
includes taxes & fees
May 10 - May 11
Candlewood Suites Annapolis by IHG

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,005 reviews)
"Clean room, amenities were great. Breakfast very good and parking safe. "
United States
Adriana M
The price is CA $103
CA $118 total
includes taxes & fees
Apr 30 - May 1
Best Western Annapolis

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (381 reviews)
"Parking was easy, could see car from room, coffee and tea offered all day, bike sign out was easy"
United States
Katy
The price is CA $205
CA $226 total
includes taxes & fees
May 3 - May 4
Knapps Narrows Marina & Inn

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,006 reviews)
"Great stay!"
United States
Jehane
The price is CA $165
CA $188 total
includes taxes & fees
May 24 - May 25
DoubleTree by Hilton Hotel Annapolis

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (370 reviews)
"Great hotel, very clean & quiet. "
United States
Janet
The price is CA $197
CA $217 total
includes taxes & fees
May 10 - May 11
Fairfield Inn & Suites by Marriott Easton

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is CA $247
CA $274 total
includes taxes & fees
May 5 - May 6
Inn at Huntingfield Creek
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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Stay near popular Chester attractions

Learn more about Chester

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

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Open Photo by Patricia Knorr

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Frequently asked questions

What is the best area to stay in Chester?
For most visitors, the best area to stay in Chester is along Kent Narrows, which offers convenient access to the water and local amenities.

This area is the main hub for visitors, with many hotels, restaurants, and marinas lining the waterfront. It's located directly on the Kent Narrows waterway, connecting the Chester River to the Chesapeake Bay. You'll find a mix of seafood restaurants, shops, and places to enjoy water activities. Most establishments are easily accessible from Kent Narrows Road.

Couples looking for a relaxing getaway will appreciate the waterfront hotels in Kent Narrows. Many offer rooms with water views and balconies, providing a pleasant setting for unwinding. You can enjoy strolls along the docks, dine at restaurants with outdoor seating overlooking the water, and easily access boat tours or fishing charters.

For travellers looking for a convenient base to explore the wider Eastern Shore, staying in Kent Narrows is also excellent.
When is the best time to go to Chester?
The best time to go to Chester, Maryland, is during the spring (late April to early June) and autumn (September to October) months. These periods offer pleasant weather ideal for exploring the area.

Spring brings comfortable temperatures, typically ranging from 15°C to 25°C, and the landscape is lush with new growth. It's a great time for outdoor activities like cycling along the Cross Island Trail or visiting the local wineries. The breezes off the Chesapeake Bay are particularly refreshing.

Autumn also provides agreeable weather, with temperatures usually between 10°C and 20°C, and the changing foliage creates a scenic backdrop. This season is superb for enjoying seafood festivals or simply taking a leisurely drive across the Kent Narrows Bridge to admire the views.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chester.
How can I save on a Chester hotel booking with Expedia?
Members always get our best prices. Find our best Chester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Chester hotel?
Prices for hotels in Chester often vary, but you can find a great deal from CA $118 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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