Photo by Patricia Knorr

Chester hotels from HK$631

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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, (934)
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$752 total
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (825)
Escape to this peaceful hotel offering free breakfast, WiFi, and parking. The seasonal outdoor pool provides refreshing relaxation, while the fitness centre keeps your workout routine intact. Located near Talbot Massage and Easton Cycle and Sport, with exceptionally helpful staff.
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is HK$629
HK$691 total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn
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)
This Grasonville hotel provides a peaceful environment with a seasonal outdoor pool and complimentary breakfast, WiFi, and parking. Located near Chesapeake Bay Environmental Centre and Queenstown Harbour Golf Links for easy exploration.
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is HK$662
HK$734 total
includes taxes & fees
21 Dec - 22 Dec
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, (1003)
Ideally located near restaurants and walking trails, this Grasonville getaway offers superior rooms with spectacular sunset views over the water. Enjoy the indoor pool, hot tub, and sauna after exploring nearby Chesapeake Bay Environmental Centre.
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is HK$649
HK$721 total
includes taxes & fees
22 Dec - 23 Dec
Best Western Kent Narrows Inn
Hypo-allergenic bedding, desk, blackout curtains, iron/ironing board
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, (1006)
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.
"Cookies and coffee at check in .excellent staff "
United States
Cheryl
The price is HK$741
HK$845 total
includes taxes & fees
5 Jan - 6 Jan 2026
Country Inn & Suites by Radisson, Annapolis, MD
Exterior
Hampton Inn Easton

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (553)
Wake up to a complimentary breakfast before exploring nearby Easton Cycle and Sport. This hotel offers an indoor pool for year-round swimming and a fitness centre. Business travellers appreciate the free WiFi and parking with helpful staff.
"all excellent with kudos to staff and the breakfast cook."
United States
JOSEPH
The price is HK$849
HK$934 total
includes taxes & fees
15 Jan - 16 Jan 2026
Hampton Inn Easton
Exterior
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
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$654
HK$745 total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Annapolis
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, (1002)
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$892 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Kent Island Marina
Living area
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, (1008)
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$617
HK$703 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Annapolis Downtown
Front of property
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is HK$1,044
HK$1,190 total
includes taxes & fees
28 Dec - 29 Dec
Anchored Inn at Hidden Harbour Marina
Free daily buffet breakfast
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$623
HK$710 total
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Inn Express & Suites Annapolis by IHG
Terrace/patio
The Tidewater Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (842)
Luxurious retreat featuring Hunters' Tavern serving regional fare for all meals. The full-service spa offers deep-tissue massages and body treatments, while the terrace and garden provide peaceful spaces. Located near Avalon Theatre with free WiFi and parking.
"Friendly staff, spotless room, great location. "
United States
Steven
The price is HK$1,393
HK$1,533 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Tidewater Inn
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$856
HK$950 total
includes taxes & fees
21 Dec - 22 Dec
Hyatt Place Kent Narrows & Marina
Exterior
Best Western Annapolis

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1007)
"Parking was safe and free. Staff from breakfast did good service although breakfast was the same for 3 days. Location was perfect."
Canada
Ermelita
The price is HK$554
HK$631 total
includes taxes & fees
28 Dec - 29 Dec
Best Western Annapolis
Garden
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, (1011)
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$594
HK$677 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Hotel Annapolis
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 HK$1,051
HK$1,499 total
includes taxes & fees
1 Jan - 2 Jan 2026
Wylder Tilghman Island
Aerial view
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$1,516 total
includes taxes & fees
16 Dec - 17 Dec
Kent Island Resort
Hypo-allergenic bedding, down duvets, in-room safe, desk
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
Front of property
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1002)
Experience serene stays at this peaceful inn with seasonal outdoor pool and garden terrace. Located conveniently near Saint Michaels Village and Classic Motor Museum, guests appreciate the helpful staff, clean rooms, and complimentary breakfast, WiFi, and parking.
"clean and comfy, friendly staff"
United States
Tamara
The price is HK$857
HK$943 total
includes taxes & fees
16 Dec - 17 Dec
St Michaels Inn
Exterior
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (361)
Discover serenity on the water at this Tilghman hotel with marina access, seasonal outdoor pool, and complimentary kayaking adventures. Comfortable rooms include refrigerators and microwaves, while free breakfast, WiFi and parking enhance your Chesapeake Bay getaway.
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
The price is HK$934
HK$1,028 total
includes taxes & fees
16 Dec - 17 Dec
Knapps Narrows Marina & 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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Great for a family with kids. Staff was patient and kind. Rooms were comfortable pool was a bonus. "
Melanie 2-night trip
Posted 14 hours 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 HK$554 per night from 28 Dec to 29 Dec
HK$554
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 13.8 mi (22.2 km) from the heart of Chester, DoubleTree by Hilton Hotel Annapolis 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 Crowne Plaza Annapolis by IHG. 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. Features free self parking, an indoor pool and complimentary wireless Internet access. Country Inn & Suites by Radisson, Annapolis, MD 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 Sandy Point Beach and Queenstown Harbor Golf Club 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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