A boat docked at a pier during twilight with a city skyline in the background.

Find hotels in Chester, MD from ฿3,459

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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)
"Everything about this hotel was excellent and I would highly recommend staying here"
United States
David
The price is ฿4,626
฿5,088 total
includes taxes & fees
8 Jul - 9 Jul
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, (930 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is ฿3,328
฿3,694 total
includes taxes & fees
19 Jul - 20 Jul
Quality Inn Grasonville near Kent Island

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 ฿4,166
฿4,624 total
includes taxes & fees
12 Jul - 13 Jul
Best Western Kent Narrows Inn

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 ฿4,498
฿4,947 total
includes taxes & fees
19 Jul - 20 Jul
Fairfield Inn & Suites by Marriott Easton

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 ฿5,158
฿5,674 total
includes taxes & fees
19 Jul - 20 Jul
Holiday Inn Express Easton by IHG

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 ฿3,366
฿3,703 total
includes taxes & fees
28 Jul - 29 Jul
Quality Inn

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (491 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is ฿8,032
฿9,157 total
includes taxes & fees
16 Jul - 17 Jul
Anchored Inn at Hidden Harbour Marina

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 ฿2,836
฿3,120 total
includes taxes & fees
15 Jul - 16 Jul
Econo Lodge Easton Route 50

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (155 reviews)
"Enjoyed our stay it was very quaint, beautiful surroundings very helpful and friendly staff. We would highly recommend!"
United States
Mercedes
The price is ฿5,416
฿7,142 total
includes taxes & fees
13 Jul - 14 Jul
Kent Island Resort

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (784 reviews)
"Great Stay!!"
United States
Richard
The price is ฿6,057
฿6,723 total
includes taxes & fees
20 Jul - 21 Jul
Hyatt Place Kent Narrows & Marina

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 ฿3,145
฿3,459 total
includes taxes & fees
14 Jul - 15 Jul
St Michaels Inn

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,023 reviews)
"Good location, great room, and a great staff."
United States
Marie
The price is ฿3,701
฿4,219 total
includes taxes & fees
15 Jul - 16 Jul
DoubleTree by Hilton Hotel Annapolis

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 ฿2,754
฿3,139 total
includes taxes & fees
14 Jul - 15 Jul
Village Inn Annapolis MD

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (576 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 ฿4,256
฿4,681 total
includes taxes & fees
19 Jul - 20 Jul
Hampton Inn Easton

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 ฿4,744
฿5,266 total
includes taxes & fees
13 Jul - 14 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (1,051 reviews)
"Friendly staff, easy parking, great breakfast"
United States
Theresa
The price is ฿4,126
฿4,704 total
includes taxes & fees
8 Jul - 9 Jul
Country Inn & Suites by Radisson, Annapolis, MD

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,001 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 ฿4,966
฿5,513 total
includes taxes & fees
6 Aug - 7 Aug
Hilton Garden Inn Kent Island Marina

Hummingbird Inn

Hummingbird Inn
3.5 star property
Easton
10.0 out of 10, Exceptional, (92 reviews)
" Staff is super friendly. The rooms were very clean and the breakfast was wonderful."
United States
Lewis
The price is ฿9,823
฿10,806 total
includes taxes & fees
15 Jul - 16 Jul
Hummingbird Inn

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,003 reviews)
"We stayed 6 nights and breakfast was good every day."
United States
Daniel Glen Zechenelly
The price is ฿4,626
฿5,273 total
includes taxes & fees
12 Jul - 13 Jul
SpringHill Suites by Marriott Annapolis

Queenstown Harbor Golf Resort

Queenstown Harbor Golf Resort
2.5 star property
Queenstown
The price is ฿33,143
฿36,789 total
includes taxes & fees
15 Jul - 16 Jul
Queenstown Harbor Golf Resort
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!

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

More cheap stays in Chester

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 traveller data. Two other options for your stay in the area are DoubleTree by Hilton Hotel Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or 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 bookings are refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you booked a non-refundable reservation, it may still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What are some accommodation options 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 that offer an on-site 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 accommodation options 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. Take a look at what more there is 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 temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chester is 1414 mm.

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