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Check prices for these dates

This weekend
Jul 10 - Jul 12
Next weekend
Jul 17 - Jul 19

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Our top choices for Chester hotels

Front of property

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,008 reviews)
"Great location, modern rooms compared to area offerings."
United States
Shruti
The price is ļæ„13,875
ļæ„15,263 total
includes taxes & fees
Jul 26 - Jul 27
St Michaels Inn
Exterior

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (898 reviews)
"A good value."
United States
Alexander
The price is ļæ„16,391
ļæ„18,031 total
includes taxes & fees
Aug 2 - Aug 3
Quality Inn
Desk, free WiFi, bed sheets

Econo Lodge Easton Route 50

Econo Lodge Easton Route 50
2.5 star property
Easton
6.6 out of 10, (394 reviews)
"Easy check in, clean and comfortable room. "
United States
michael
The price is ļæ„13,793
ļæ„15,173 total
includes taxes & fees
Jul 19 - Jul 20
Econo Lodge Easton Route 50
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (930 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is ļæ„16,134
ļæ„17,909 total
includes taxes & fees
Jul 30 - Jul 31
Quality Inn Grasonville near Kent Island
Lobby

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (379 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 ļæ„21,805
ļæ„23,986 total
includes taxes & fees
Jul 26 - Jul 27
Fairfield Inn & Suites by Marriott Easton
Lobby

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)
"Everything about this hotel was excellent and I would highly recommend staying here"
United States
David
The price is ļæ„22,426
ļæ„24,669 total
includes taxes & fees
Jul 8 - Jul 9
Best Western Plus Easton Inn & Suites
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,007 reviews)
"Good hotel for the price"
United States
Brenda
The price is ļæ„20,198
ļæ„22,419 total
includes taxes & fees
Jul 22 - Jul 23
Best Western Kent Narrows Inn
Bar (on property)

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (575 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 ļæ„20,632
ļæ„22,696 total
includes taxes & fees
Jul 19 - Jul 20
Hampton Inn Easton
Free daily buffet breakfast

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (614 reviews)
"A clean hotel and a great breakfast."
United States
Maura
The price is ļæ„25,008
ļæ„27,509 total
includes taxes & fees
Jul 19 - Jul 20
Holiday Inn Express Easton by IHG
Lobby

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, (1,047 reviews)
"Friendly staff, easy parking, great breakfast"
United States
Theresa
The price is ļæ„20,094
ļæ„22,907 total
includes taxes & fees
Jul 8 - Jul 9
Country Inn & Suites by Radisson, Annapolis, MD
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,021 reviews)
"The staff was great, nice hotel bar and the location was close to everything!"
United States
Diane
The price is ļæ„18,020
ļæ„20,542 total
includes taxes & fees
Jul 8 - Jul 9
DoubleTree by Hilton Hotel Annapolis
Lobby

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1,006 reviews)
"Breakfast was excellent and parking was convenient and safe"
United States
Paul
The price is ļæ„16,231
ļæ„18,503 total
includes taxes & fees
Jul 14 - Jul 15
Hilton Garden Inn Annapolis
Fridge, microwave

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (509 reviews)
"The room was very nice, clean and quiet. Great location"
United States
William
The price is ļæ„13,391
ļæ„15,266 total
includes taxes & fees
Jul 12 - Jul 13
Village Inn Annapolis MD
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,880 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is ļæ„14,548
ļæ„22,103 total
includes taxes & fees
Jul 13 - Jul 14
Historic Inns of Annapolis
Indoor pool

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,006 reviews)
"Great place to stay for a short visit to Annapolis."
United States
Jeffrey
The price is ļæ„19,770
ļæ„22,538 total
includes taxes & fees
Jul 19 - Jul 20
Crowne Plaza Annapolis by IHG
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (155 reviews)
"It was such a lovely quaint resort. I loved everything about staying there. Thank you."
United States
Sue
The price is ļæ„26,337
ļæ„34,732 total
includes taxes & fees
Jul 13 - Jul 14
Kent Island Resort
Dining

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,006 reviews)
"Clean, reasonably priced , great staff and excellent breakfast!"
United States
Brian
The price is ļæ„15,607
ļæ„17,791 total
includes taxes & fees
Jul 9 - Jul 10
Best Western Annapolis
Exterior

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.0 out of 10, Very Good, (1,004 reviews)
"Clean, breakfast was great"
United States
Robert Y. Vaughn
The price is ļæ„15,610
ļæ„17,796 total
includes taxes & fees
Aug 2 - Aug 3
Hampton Inn & Suites Annapolis
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, (1,004 reviews)
"Beautiful view!!! Clean hotel and very nice helpful staff. Would stay again."
United States
Michele
The price is ļæ„21,715
ļæ„24,104 total
includes taxes & fees
Aug 3 - Aug 4
Holiday Inn Express Annapolis East-Kent Island by IHG
Property amenity

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,001 reviews)
"A good stay"
United States
Anne
The price is ļæ„18,393
ļæ„20,968 total
includes taxes & fees
Jul 27 - Jul 28
Courtyard by Marriott 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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Stay near popular Chester attractions

Chesapeake Exploration Center

Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.
See properties

Learn more about Chester

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

See all hotels in Chester
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Clean, simple, and exactly what I needed. The staff was incredibly friendly and welcoming. Will definitely stay here again!"
Aline 2-night trip
Posted less than an hour ago
St Michaels Inn

More cheap stays in Chester

St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
The price is ļæ„13,875 per night from Jul 26 to Jul 27
ļæ„13,875
ļæ„15,263 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Located 10.8 mi (17.3 km) from the heart of Chester, Historic Inns of Annapolis is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are DoubleTree by Hilton Hotel Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Chester.
What's the top vacation rental in Chester?
Charming Annapolis WaterVIEW Home: You might want to consider this vacation home rental near Chester, which is located on the waterfront and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. See all vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes! You'll find that most hotel room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
Where can I learn more about changing or cancelling my trip to Chester?
To find more details about rescheduling or cancelling your trip to Chester, head over to our customer service page.
What are some accommodations with pools in Chester?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. Country Inn & Suites by Radisson, Annapolis, MD and St Michaels Inn are a couple of other choices with an onsite pool. View all hotels with pools in Chester.
What is staying in Chester like?
Visitors can enjoy all that Chester has to offer including the waterfront, seafood restaurants, and golf courses. In Chester, there are 9 hotels and other accommodations to choose from. Find out more about Chester.
What is there to see in Chester?
Places to visit in the wider area include Northern Chesapeake Bay, Matapeake State Park, and Chesapeake Bay Environmental Center. You'll also find Love Point State Park and Sandy Point Beach in the area. Check out what more to see and do in Expedia's Chester guide.
What's the weather like in Chester?
The hottest months are usually July and August with an average temp of 74Ā°F, while the coldest months are January and February with an average of 39Ā°F. Average annual precipitation for Chester is 56 inches.

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