Photo by Patricia Knorr

Chester hotels from HK$631

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12 Dec - 13 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

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (932)
Discover tranquility on Kent Island with beautiful bay views and a seasonal outdoor pool. This hotel sits right on a bike trail with rentals available on-site. Enjoy complimentary breakfast and explore nearby Chesapeake Bay Environmental Centre after a quiet night's rest.
"It was very comfortable and clean"
United States
Maria
The price is HK$677
HK$751 total
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1001)
Overlooking the bay in Grasonville, this hotel offers an indoor pool and fitness centre for active travellers. Explore nearby Chesapeake Bay Environmental Centre, then unwind with drinks at the bar. Rooms include microwaves and refrigerators for added convenience.
"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
21 Dec - 22 Dec
Hilton Garden Inn Kent Island Marina
Reception
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1003)
Located just 5 minutes from US Naval Academy, this hotel offers convenient access to Annapolis Harbour Centre and Westfield Annapolis Mall. Enjoy the 24-hour fitness centre, restaurant serving 3 meals daily, and garden. Guests particularly praise the helpful staff and prime location.
"Great place!"
United States
Tawnya
The price is HK$593
HK$676 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

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (674)
Experience a refreshing stay at this waterfront hotel with an indoor pool and helpful staff. Just minutes from Chesapeake Bay Environmental Centre and Paul Reed Smith Guitars, enjoy convenient access to local attractions with free WiFi and parking.
"Great view, good ambiance all around"
United States
Dianne
The price is HK$903
HK$1,003 total
includes taxes & fees
14 Dec - 15 Dec
Hyatt Place Kent Narrows & Marina
Property amenity
The Westin Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
Discover peaceful luxury in Annapolis with a full-service spa offering massages and facials. After enjoying Captain's Daughter restaurant, take a refreshing dip in the indoor pool or maintain your workout routine at the 24-hour fitness centre.
"Spectacular "
United States
Dennis
The price is HK$1,198
HK$1,366 total
includes taxes & fees
16 Dec - 17 Dec
The Westin Annapolis
Exterior
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very good, (1001)
Located within a 10-minute drive of US Naval Academy, this hotel offers a seasonal outdoor pool and fitness centre. Guests praise the helpful staff and free breakfast. Annapolis Harbour Centre Shopping Centre is nearby for all your needs.
"I had a great experience at my stay at Hampton "
United States
Idris O
The price is HK$703
HK$802 total
includes taxes & fees
18 Dec - 19 Dec
Hampton Inn & Suites Annapolis
Premium bedding, down duvets, pillow-top beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (881)
Located steps from Ego Alley and Susan Campbell Park, this hotel offers Caribbean cuisine at Pussers Grille and panoramic harbour views. Enjoy luxury yacht sightings, a 24-hour fitness centre, and quick access to the US Naval Academy.
"Great location, nice and clean "
United States
Micah
The price is HK$1,382
HK$1,576 total
includes taxes & fees
21 Dec - 22 Dec
Annapolis Waterfront Hotel, Autograph Collection
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1000)
Dive into comfort at this Annapolis hotel with a serene indoor pool, on-site restaurant, and bar. Just 10 minutes from the Naval Academy and steps from Westfield Mall, guests love the peaceful atmosphere, attentive staff, and clean rooms.
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is HK$942
HK$1,073 total
includes taxes & fees
4 Jan - 5 Jan 2026
Crowne Plaza Annapolis by IHG
Reception
Kent Island Resort

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$1,116
HK$1,517 total
includes taxes & fees
14 Dec - 15 Dec
Kent Island Resort
Property amenity
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1001)
Situated just a short drive from the US Naval Academy, this hotel offers American cuisine at The Bistro. Guests praise the peaceful atmosphere, helpful staff, and clean rooms. Free WiFi and parking enhance your stay near Annapolis Harbour Centre.
"Wonderful stay. "
United States
Angela
The price is HK$653
HK$745 total
includes taxes & fees
28 Dec - 29 Dec
Courtyard by Marriott Annapolis
Lobby
Country Inn & Suites by Radisson, Annapolis, MD

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, (1002)
Just 10 minutes from the US Naval Academy, this serene hotel offers free parking and WiFi. Unwind in the indoor pool and hot tub after exploring nearby Westfield Annapolis Mall and local restaurants. Guests consistently praise the peaceful atmosphere and attentive staff.
"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$741
HK$844 total
includes taxes & fees
1 Jan - 2 Jan 2026
Country Inn & Suites by Radisson, Annapolis, MD
Meeting facility
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1898)
Immerse in Maryland's maritime heritage at this historic hotel with a 24-hour fitness centre and garden terrace. Just a short walk from the US Naval Academy and colonial attractions, this hotel offers comfortable beds and exceptional service.
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
Historic Inns of Annapolis
Lobby
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1000)
"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
In-room safe, desk, laptop workspace, blackout curtains
Holiday Inn Express & Suites Annapolis by IHG

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)
Wake up to a delicious buffet breakfast at this Annapolis hotel, just 5 minutes from the US Naval Academy. Enjoy complimentary WiFi and parking, plus a 24-hour fitness centre. Located within easy walking distance to restaurants and shops.
"Clean room and friendly staff! "
United States
Silvia
The price is HK$622
HK$710 total
includes taxes & fees
10 Jan - 11 Jan 2026
Holiday Inn Express & Suites Annapolis by IHG
Lobby
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1007)
Experience Art Deco style at this city centre Annapolis hotel, just minutes from the US Naval Academy. Enjoy regional cuisine at Kitchen on West St, unwind at the bar/lounge, or maintain your routine in the 24-hour fitness centre.
"Great value for stay with breakfast included "
United States
Aisling
The price is HK$616
HK$702 total
includes taxes & fees
28 Dec - 29 Dec
Hilton Garden Inn Annapolis Downtown
Free daily buffet breakfast
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (962)
Located minutes from US Naval Academy, this peaceful hotel offers spacious suites and complimentary breakfast. The outdoor pool provides relaxation after exploring nearby shopping centers, while friendly staff ensure a comfortable stay close to major highways.
"Nice breakfast, clean room, great parking"
United States
Amy
The price is HK$708
HK$807 total
includes taxes & fees
11 Jan - 12 Jan 2026
Sonesta ES Suites Annapolis
Free daily self-service breakfast
SpringHill Suites by Marriott Annapolis

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$721
HK$822 total
includes taxes & fees
18 Dec - 19 Dec
SpringHill Suites by Marriott Annapolis
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, (429)
Located in Stevensville with easy access to Paul Reed Smith Guitars and Northern Chesapeake Bay, this hotel offers spa treatments, an outdoor pool, and a café. Enjoy free WiFi and parking while the helpful staff ensures a memorable stay.
"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$1,785 total
includes taxes & fees
15 Dec - 16 Dec
The Inn at Chesapeake Bay Beach Club
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1002)
Just a 5-minute drive from US Naval Academy, this hotel offers a calm atmosphere with comfortable beds and helpful staff. Enjoy Trophy Room for dinner, a bar/lounge, and complimentary bike rentals to explore nearby attractions and dining options.
"Very nice hotel. The dog park could have better lighting. "
United States
Andrew
The price is HK$1,005
HK$1,146 total
includes taxes & fees
21 Dec - 22 Dec
Graduate by Hilton Annapolis
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, (120)
This charming Tilghman inn offers stunning water views with convenient access to Tilghman Island Marina. Enjoy a complimentary breakfast before lounging by the seasonal outdoor pool or exploring the garden. The friendly staff and relaxing bar enhance your Eastern Shore getaway.
"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
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

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Clean. Friendly. Balcony. Value"
jennifer 1-night trip
Posted 2 days ago
Courtyard by Marriott Annapolis

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is HK$553 per night from 28 Dec to 29 Dec
HK$553
HK$631 total
28 Dec - 29 Dec
includes taxes & fees
7.6/10 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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