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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, (1,006 reviews)
"Everything about this hotel was excellent and I would highly recommend staying here"
United States
David
The price is NZ$271
includes taxes & fees
1 July - 2 July
Best Western Plus Easton Inn & Suites

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (927 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is NZ$196
includes taxes & fees
8 July - 9 July
Quality Inn Grasonville near Kent Island

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,000 reviews)
"Great location, modern rooms compared to area offerings."
United States
Shruti
The price is NZ$177
includes taxes & fees
7 July - 8 July
St Michaels Inn

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (150 reviews)
"It was such a lovely quaint resort. I loved everything about staying there. Thank you."
United States
Sue
The price is NZ$345
includes taxes & fees
5 July - 6 July
Kent Island Resort

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (612 reviews)
"A clean hotel and a great breakfast."
United States
Maura
The price is NZ$280
includes taxes & fees
12 July - 13 July
Holiday Inn Express Easton by IHG

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (895 reviews)
"A good value."
United States
Alexander
The price is NZ$197
includes taxes & fees
26 July - 27 July
Quality Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Good hotel for the price"
United States
Brenda
The price is NZ$246
includes taxes & fees
7 July - 8 July
Best Western Kent Narrows Inn

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,020 reviews)
"The staff was great, nice hotel bar and the location was close to everything!"
United States
Diane
The price is NZ$192
includes taxes & fees
5 July - 6 July
DoubleTree by Hilton Hotel Annapolis

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (895 reviews)
"Loved everything about this beautiful hotel."
United States
Diane
The price is NZ$341
includes taxes & fees
12 July - 13 July
The Tidewater Inn

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)
"The hotel was clean and looked nice, the bed was very soft in the middle and uncomfortable and the $14 breakfast was no where near worth it."
United States
Sandy
The price is NZ$304
includes taxes & fees
19 July - 20 July
Hilton Garden Inn Kent Island Marina

Sandaway Suites & Beach

Sandaway Suites & Beach
3.0 star property
Oxford
9.4 out of 10, Exceptional, (173 reviews)
"It was a beautiful stay!"
United States
Eliza
The price is NZ$339
includes taxes & fees
6 July - 7 July
Sandaway Suites & Beach

Econo Lodge Easton Route 50

Econo Lodge Easton Route 50
2.5 star property
Easton
6.6 out of 10, (393 reviews)
"Easy check in, clean and comfortable room. "
United States
michael
The price is NZ$175
includes taxes & fees
7 July - 8 July
Econo Lodge Easton Route 50

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (490 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is NZ$488
includes taxes & fees
7 July - 8 July
Anchored Inn at Hidden Harbour Marina

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,045 reviews)
"Friendly staff, easy parking, great breakfast"
United States
Theresa
The price is NZ$221
includes taxes & fees
12 July - 13 July
Country Inn & Suites by Radisson, Annapolis, MD

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, (1,000 reviews)
"Beautiful view!!! Clean hotel and very nice helpful staff. Would stay again."
United States
Michele
The price is NZ$273
includes taxes & fees
20 July - 21 July
Holiday Inn Express Annapolis East-Kent Island by IHG

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (572 reviews)
"I have enjoyed Hampton Inns for years and this was no exception. The room and service were exceptional."
United States
Matthew
The price is NZ$285
includes taxes & fees
12 July - 13 July
Hampton Inn Easton

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,008 reviews)
"Great place to stay for a short visit to Annapolis."
United States
Jeffrey
The price is NZ$230
includes taxes & fees
12 July - 13 July
Crowne Plaza Annapolis by IHG

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (378 reviews)
"Had a short stay in Easton to visit family. The hotel and staff were wonderful. Breakfast was decent. I would recommend this hotel and plan to stay here in future."
United States
Linda
The price is NZ$263
includes taxes & fees
5 July - 6 July
Fairfield Inn & Suites by Marriott Easton

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,010 reviews)
"Clean, reasonably priced , great staff and excellent breakfast!"
United States
Brian
The price is NZ$183
includes taxes & fees
5 July - 6 July
Best Western Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,003 reviews)
"Breakfast was excellent and parking was convenient and safe"
United States
Paul
The price is NZ$180
includes taxes & fees
6 July - 7 July
Hilton Garden Inn Annapolis
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Stay near popular Chester attractions

Learn more about Chester

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

A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

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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, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 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 hotel booking in Chester with Expedia?
One Key™ – Expedia's free travel rewards programme – gives you instant access to perks and Member Prices on Chester hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Chester?
Prices for hotels in Chester often vary, but you can find a great deal from NZ$177 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 our cheapest rates.

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