Chester Hotels from S$100

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
13 Jan - 14 Jan
Tomorrow
14 Jan - 15 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chester hotels

Exterior
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (833 reviews)
"Checkin staff was great. The motel is advertised as a HOTEL, and it very clearly is not."
United States
Jennifer
The price is S$120
includes taxes & fees
20 Jan - 21 Jan
Quality Inn
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, (950 reviews)
"Great staff, clean room, nice view!"
United States
Quiana
The price is S$136
includes taxes & fees
24 Jan - 25 Jan
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1,001 reviews)
"Spacious room, friendly staff, nice bathroom. Everyone is very accommodating."
United States
DONNA
The price is S$168
includes taxes & fees
14 Jan - 15 Jan
Best Western Plus Easton Inn & Suites
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, (1,006 reviews)
"Great stay "
United States
Jose Miguel
The price is S$110
includes taxes & fees
8 Feb - 9 Feb
DoubleTree by Hilton Hotel Annapolis
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, (867 reviews)
"Great hotel. Stayed multiple times at this location "
United States
Nicholas
The price is S$123
includes taxes & fees
24 Jan - 25 Jan
Quality Inn Grasonville near Kent Island
Meeting facility
The Tidewater Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (845 reviews)
"Friendly staff, spotless room, great location. "
United States
Steven
The price is S$253
includes taxes & fees
14 Jan - 15 Jan
The Tidewater Inn
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, (1,001 reviews)
"Breakfast menu was great! Pool and hot tub were nice!"
United States
Terrence
The price is S$134
includes taxes & fees
8 Feb - 9 Feb
Country Inn & Suites by Radisson, Annapolis, MD
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, (1,000 reviews)
"Good value and close to downtown."
United States
John
The price is S$131
includes taxes & fees
21 Jan - 22 Jan
St Michaels Inn
Reception
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130 reviews)
"Beautiful and peaceful property!"
United States
Jerry
The price is S$226
includes taxes & fees
18 Jan - 19 Jan
Kent Island Resort
Exterior
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (365 reviews)
"nice clean room staff very nice would stay again "
United States
mario
The price is S$141
includes taxes & fees
14 Jan - 15 Jan
Knapps Narrows Marina & Inn
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, (1,014 reviews)
"Great value for stay with breakfast included "
United States
Aisling
The price is S$131
includes taxes & fees
8 Feb - 9 Feb
Hilton Garden Inn Annapolis Downtown
Indoor pool
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, (1,002 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is S$119
includes taxes & fees
20 Jan - 21 Jan
Best Western Kent Narrows Inn
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 reviews)
"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 S$205
includes taxes & fees
11 Feb - 12 Feb
Holiday Inn Express Easton by IHG
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, (1,000 reviews)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
The price is S$120
includes taxes & fees
1 Feb - 2 Feb
Hilton Garden Inn Annapolis
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, (473 reviews)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is S$197
includes taxes & fees
15 Jan - 16 Jan
Anchored Inn at Hidden Harbour Marina
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, (699 reviews)
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is S$169
includes taxes & fees
19 Jan - 20 Jan
Hyatt Place Kent Narrows & Marina
Lobby
Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (191 reviews)
"The staff was extremely pleasant and enjoyable to work with!! "
United States
Laura
The price is S$123
includes taxes & fees
16 Jan - 17 Jan
Candlewood Suites Annapolis by IHG
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, (1,001 reviews)
"We keep coming back to the hotel with every visit to Annapolis. "
United States
Catherine
The price is S$123
includes taxes & fees
1 Feb - 2 Feb
Courtyard by Marriott Annapolis
Exterior
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (91 reviews)
"Very relaxing stay."
United States
Anne
The price is S$221
includes taxes & fees
15 Jan - 16 Jan
Wylder Tilghman Island
Lake
Inn at Huntingfield Creek

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (59 reviews)
"Quiet. Friendly staff. Beautiful grounds. Very clean."
United States
Brian
Inn at Huntingfield Creek
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"H"
William 2-night trip
Posted 5 days ago
Historic Inns of Annapolis

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is S$100 per night from 8 Feb to 9 Feb
S$100
8 Feb - 9 Feb
includes taxes & fees
7.6/10 Good! (1,000 reviews)

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 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?
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 Sonesta ES Suites 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 Chesapeake Bay Environmental Center. You'll also find Love Point State Park and Eastern Neck National Wildlife Refuge 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.

Explore a world of travel with Expedia