Photo by Patricia Knorr

Chester hotels from HK$647

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9 Dec - 10 Dec
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12 Dec - 14 Dec
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Our top choices for Chester hotels

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, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is HK$677
HK$752 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1004)
"We stayed overnight, coming to meet some people for a business meeting. Monica at the front desk provided great customer service and was extremely helpful in accommodating us. "
United States
Anthony
The price is HK$803
HK$891 total
includes taxes & fees
23 Dec - 24 Dec
Hilton Garden Inn Kent Island Marina
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1014)
"Great place!"
United States
Tawnya
The price is HK$594
HK$677 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Hotel Annapolis
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.6 out of 10, Exceptional, (674)
"Great view, good ambiance all around"
United States
Dianne
The price is HK$903
HK$1,003 total
includes taxes & fees
23 Dec - 24 Dec
Hyatt Place Kent Narrows & Marina
View from property
The Westin Annapolis

The Westin Annapolis

4.0 star property
Annapolis
8.6 out of 10, Excellent, (1003)
"Spectacular "
United States
Dennis
The price is HK$1,198
HK$1,366 total
includes taxes & fees
14 Dec - 15 Dec
The Westin Annapolis
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is HK$993
HK$1,376 total
includes taxes & fees
11 Dec - 12 Dec
Kent Island Resort
Premium bedding, down duvets, pillow-top beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (881)
"Great location, nice and clean "
United States
Micah
The price is HK$1,382
HK$1,576 total
includes taxes & fees
15 Dec - 16 Dec
Annapolis Waterfront Hotel, Autograph Collection
Premium bedding, pillow-top beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 star property
Annapolis
8.2 out of 10, Very good, (1002)
"I had a great experience at my stay at Hampton "
United States
Idris O
The price is HK$673
HK$767 total
includes taxes & fees
17 Dec - 18 Dec
Hampton Inn & Suites Annapolis
Exterior
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
"Wonderful stay. "
United States
Angela
The price is HK$755
HK$860 total
includes taxes & fees
29 Dec - 30 Dec
Courtyard by Marriott Annapolis
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 star property
Annapolis
8.8 out of 10, Excellent, (1007)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is HK$755
HK$860 total
includes taxes & fees
15 Dec - 16 Dec
Crowne Plaza Annapolis by IHG
Hypo-allergenic bedding, desk, blackout curtains, iron/ironing board
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, (1007)
"Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet."
United States
Paul
The price is HK$679
HK$774 total
includes taxes & fees
29 Dec - 30 Dec
Country Inn & Suites by Radisson, Annapolis, MD
Hypo-allergenic bedding, down duvets, in-room safe, desk
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3.0 star property
Annapolis
8.2 out of 10, Very good, (1006)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
The price is HK$579
HK$660 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Annapolis
Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1905)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
Historic Inns of Annapolis
Free daily buffet breakfast
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
Annapolis
8.2 out of 10, Very good, (1000)
"Clean room and friendly staff! "
United States
Silvia
The price is HK$622
HK$710 total
includes taxes & fees
20 Dec - 21 Dec
Holiday Inn Express & Suites Annapolis by IHG
Living area
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3.0 star property
Annapolis
8.6 out of 10, Excellent, (1003)
"Great value for stay with breakfast included "
United States
Aisling
The price is HK$616
HK$702 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Annapolis Downtown
Front of property – evening/night
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, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is HK$1,430
HK$1,786 total
includes taxes & fees
23 Dec - 24 Dec
The Inn at Chesapeake Bay Beach Club
Egyptian cotton sheets, premium bedding, pillow-top beds, desk
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3.0 star property
Edgewater
8.8 out of 10, Excellent, (960)
"Nice breakfast, clean room, great parking"
United States
Amy
The price is HK$708
HK$807 total
includes taxes & fees
29 Dec - 30 Dec
Sonesta ES Suites Annapolis
Free daily self-service breakfast
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1000)
"Friendly staff and comfortable rooms. We love staying here when we visit the area as a family."
United States
Jennifer
The price is HK$787
HK$897 total
includes taxes & fees
17 Dec - 18 Dec
SpringHill Suites by Marriott Annapolis
Outdoor banquet area
The Tilghman Island Inn

The Tilghman Island Inn

3.5 star property
Tilghman
9.6 out of 10, Exceptional, (120)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is HK$1,556
HK$1,712 total
includes taxes & fees
14 Dec - 15 Dec
The Tilghman Island Inn
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1002)
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is HK$1,038
HK$1,184 total
includes taxes & fees
21 Dec - 22 Dec
Graduate by Hilton 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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Clean upscale rooom..bed was amazing "
Theo 1-night trip
Posted 3 hours ago
DoubleTree by Hilton Hotel Annapolis

More cheap stays in Chester

St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
The price is HK$856 per night from 11 Dec to 12 Dec
HK$856
HK$942 total
11 Dec - 12 Dec
includes taxes & fees
8/10 Very Good! (1,001 reviews)

Hotels in Chester with star-rating

Frequently asked questions

What's the best place to stay in Chester?
Located 13.7 mi (22 km) from the heart of Chester, Crowne Plaza Annapolis by IHG is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Historic Inns of Annapolis and DoubleTree by Hilton Hotel Annapolis. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!: This highly rated holiday home rental in Chester is located on the waterfront, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. 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 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 Country Inn & Suites by Radisson, Annapolis, MD 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 12 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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