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Our top choices for Chester hotels

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, (961 reviews)
"Clean room, I enjoy staying here every time I'm in the area"
United States
Peter
The price is ฿2,969
฿3,295 total
includes taxes & fees
24 Feb - 25 Feb
Holiday Inn Express Annapolis East-Kent Island by IHG

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (846 reviews)
"Checkin staff was great. The motel is advertised as a HOTEL, and it very clearly is not."
United States
Jennifer
The price is ฿2,651
฿2,916 total
includes taxes & fees
1 Mar - 2 Mar
Quality Inn

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (875 reviews)
"Nice staff and rooms"
United States
Walter
The price is ฿2,624
฿2,913 total
includes taxes & fees
16 Mar - 17 Mar
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, (476 reviews)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is ฿4,182
฿4,768 total
includes taxes & fees
22 Feb - 23 Feb
Anchored Inn at Hidden Harbour Marina

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)
"Nice friendly staff, clean room and lobby"
United States
Joi
The price is ฿3,711
฿4,082 total
includes taxes & fees
22 Feb - 23 Feb
Best Western Plus Easton Inn & Suites

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,003 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is ฿2,931
฿3,254 total
includes taxes & fees
2 Mar - 3 Mar
Best Western Kent Narrows Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (370 reviews)
"Clean room, helpful staff, nice breakfast, beautiful views, excellent location."
United States
Denise
The price is ฿3,119
฿3,430 total
includes taxes & fees
23 Feb - 24 Feb
Knapps Narrows Marina & Inn

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,004 reviews)
"The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town. "
United States
Kathy
The price is ฿2,583
฿2,944 total
includes taxes & fees
22 Feb - 23 Feb
DoubleTree by Hilton Hotel Annapolis

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (93 reviews)
"We were"
United States
Guevara
The price is ฿3,963
฿5,732 total
includes taxes & fees
11 Mar - 12 Mar
Wylder Tilghman Island

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,001 reviews)
"Great location and friendly staff. "
United States
Shana
The price is ฿2,359
฿2,689 total
includes taxes & fees
8 Mar - 9 Mar
SpringHill Suites by Marriott Annapolis

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (597 reviews)
"Everything was great!"
United States
HEATHER
The price is ฿4,023
฿4,425 total
includes taxes & fees
15 Mar - 16 Mar
Holiday Inn Express Easton by IHG

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)
"Staff was friendly and rooms were clean. Beautiful area to visit. "
United States
Amy
The price is ฿3,554
฿3,945 total
includes taxes & fees
25 Feb - 26 Feb
Hilton Garden Inn Kent Island Marina

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121 reviews)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is ฿4,844
฿5,328 total
includes taxes & fees
21 Feb - 22 Feb
The Tilghman Island Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,001 reviews)
"Good value and close to downtown."
United States
John
St Michaels Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (853 reviews)
"Friendly staff, spotless room, great location. "
United States
Steven
The price is ฿4,958
฿5,454 total
includes taxes & fees
25 Feb - 26 Feb
The Tidewater Inn

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (717 reviews)
"Amazing location and staff!"
United States
Bobbi J.
The price is ฿3,617
฿4,015 total
includes taxes & fees
2 Mar - 3 Mar
Hyatt Place Kent Narrows & Marina

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (559 reviews)
"all excellent with kudos to staff and the breakfast cook."
United States
JOSEPH
The price is ฿3,675
฿4,043 total
includes taxes & fees
8 Mar - 9 Mar
Hampton Inn Easton

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (417 reviews)
"Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown. "
United States
Fred
The price is ฿5,585
฿6,830 total
includes taxes & fees
22 Feb - 23 Feb
The Wildset

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (178 reviews)
"Room was very nice and clean. Only thing that needs to change is the parking situation. They need more parking spaces. And they charge $30 for parking. "
United States
Cecilia
The price is ฿3,430
฿3,911 total
includes taxes & fees
24 Feb - 25 Feb
Fairfield Inn & Suites By Marriott Annapolis

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, (1,000 reviews)
"Wonderful staff, great options for breakfast, room is perfect and quiet and clean. The amenities work nicely, gym is great and Thai is where I would stay again in the future. "
United States
Amanda
The price is ฿2,844
฿3,242 total
includes taxes & fees
15 Mar - 16 Mar
Country Inn & Suites by Radisson, Annapolis, MD
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!

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

Top Chester Hotel Reviews

More cheap stays in Chester

Frequently asked questions

What's the best place to stay in Chester?
Located 14.1 mi (22.6 km) from the heart of Chester, Sonesta ES Suites Annapolis is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Graduate by Hilton Annapolis and Historic Inns of Annapolis. 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?
Sonesta ES Suites Annapolis: Offers buffet, a seasonal outdoor pool and complimentary wireless Internet access. Country Inn & Suites by Radisson, Annapolis, MD and Crowne Plaza Annapolis by IHG 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 11 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 Paul Reed Smith Guitars, Northern Chesapeake Bay and Matapeake State Park. You'll also find Chesapeake Bay Environmental Center and Love Point State Park 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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