Photo by Patricia Knorr

Find hotels in Chester, MD from ฿2,363

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26 Dec - 28 Dec
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Our top choices for Chester hotels

Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (678)
"Great view, good ambiance all around"
United States
Dianne
The price is ฿3,424
฿3,800 total
includes taxes & fees
30 Dec - 31 Dec
Hyatt Place Kent Narrows & Marina
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (939)
"It was very comfortable and clean"
United States
Maria
The price is ฿2,706
฿3,004 total
includes taxes & fees
18 Jan - 19 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (432)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is ฿5,132
฿6,488 total
includes taxes & fees
18 Jan - 19 Jan 2026
The Inn at Chesapeake Bay Beach Club
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

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ฿2,630
฿2,919 total
includes taxes & fees
19 Jan - 20 Jan 2026
Quality Inn Grasonville near Kent Island
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1000)
"Nice place "
United States
Tucker T
The price is ฿2,329
฿2,585 total
includes taxes & fees
30 Dec - 31 Dec
Best Western Kent Narrows Inn
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (129)
"Beautiful and peaceful property!"
United States
Jerry
The price is ฿3,719
฿5,211 total
includes taxes & fees
28 Dec - 29 Dec
Kent Island Resort
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1000)
"Clean and friendly staff"
United States
Lisa
The price is ฿3,548
฿3,938 total
includes taxes & fees
28 Dec - 29 Dec
Hilton Garden Inn Kent Island Marina
Horse riding
The Inn at Tacaro Estate

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (11)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The Inn at Tacaro Estate
Terrace/patio
The Tidewater Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (842)
"Friendly staff, spotless room, great location. "
United States
Steven
The price is ฿5,568
฿6,125 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Tidewater Inn
Exterior
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (828)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is ฿2,644
฿2,908 total
includes taxes & fees
5 Jan - 6 Jan 2026
Quality Inn
Outdoor banquet area
The Tilghman Island Inn

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is ฿6,377
฿7,014 total
includes taxes & fees
18 Jan - 19 Jan 2026
The Tilghman Island Inn
Exterior
Hampton Inn Easton

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (553)
"all excellent with kudos to staff and the breakfast cook."
United States
JOSEPH
The price is ฿3,757
฿4,133 total
includes taxes & fees
22 Jan - 23 Jan 2026
Hampton Inn Easton
View from property
Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
2.5 star property
Easton
9.6 out of 10, Exceptional, (367)
"Great hotel, very clean & quiet. "
United States
Janet
The price is ฿5,011
฿5,512 total
includes taxes & fees
28 Dec - 29 Dec
Fairfield Inn & Suites by Marriott Easton
Exterior
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (363)
"nice clean room staff very nice would stay again "
United States
mario
The price is ฿3,735
฿4,108 total
includes taxes & fees
27 Dec - 28 Dec
Knapps Narrows Marina & Inn
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is ฿3,665
฿5,401 total
includes taxes & fees
18 Jan - 19 Jan 2026
Wylder Tilghman Island
Front of property
The Oaks Waterfront

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
" Beautiful property, wonderful staff, excellent food service."
United States
Seth
The price is ฿12,850
฿14,135 total
includes taxes & fees
29 Dec - 30 Dec
The Oaks Waterfront
Porch
Hummingbird Inn

Hummingbird Inn

Hummingbird Inn
3.5 star property
Easton
10.0 out of 10, Exceptional, (86)
"The kindest most sweetest checkin"
United States
Nicole
Hummingbird Inn
Lobby
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1002)
"Spacious room, friendly staff, nice bathroom. Everyone is very accommodating."
United States
DONNA
The price is ฿3,702
฿4,072 total
includes taxes & fees
25 Dec - 26 Dec
Best Western Plus Easton Inn & Suites
Free daily buffet breakfast
Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (593)
"We only stayed one night but it was perfect. The room was very clean, the beds were comfortable, and the staff were very nice. "
United States
Nancy
The price is ฿4,171
฿4,588 total
includes taxes & fees
6 Jan - 7 Jan 2026
Holiday Inn Express Easton by IHG
Egyptian cotton sheets, premium bedding, pillow-top beds, desk
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (966)
"Clean, spacious, quiet, convenient location. I’d stay there again. "
United States
Michael
The price is ฿2,862
฿3,262 total
includes taxes & fees
18 Jan - 19 Jan 2026
Sonesta ES Suites 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 in 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
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"It was clean, quiet and comfortable. Will definitely come back if in the area again."
Nick 2-night trip
Posted 7 days ago
Country Inn & Suites by Radisson, Annapolis, MD

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is ฿2,073 per night from 10 Jan to 11 Jan
฿2,073
฿2,363 total
10 Jan - 11 Jan 2026
includes taxes & fees
7.6/10 Good! (1,003 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 traveller data. Two other options for your stay in the area are DoubleTree by Hilton Hotel Annapolis and Annapolis Waterfront Hotel, Autograph Collection. 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. Offers free self parking, an indoor pool and complimentary wireless Internet access. Sonesta ES Suites Annapolis and The Westin Annapolis 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 Northern Chesapeake Bay, Matapeake State Park and Love Point State Park. You'll also find Eastern Neck National Wildlife Refuge 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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