Photo by Patricia Knorr

Chester Hotels from S$114

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Top 10 trending Chester hotels

Our top choices for Chester hotels

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (890)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is S$181
includes taxes & fees
22 Sept - 23 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (615)
"Great place to stay. "
The price is S$229
includes taxes & fees
22 Sept - 23 Sept
Hyatt Place Kent Narrows & Marina

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1001)
"Great place! "
The price is S$283
includes taxes & fees
31 Aug - 1 Sept
The Westin Annapolis

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (990)
"How clean and polite the staff was "
The price is S$224
includes taxes & fees
14 Sept - 15 Sept
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very good, (1003)
"Property is in a nice location, staff were courteous and nice."
The price is S$153
includes taxes & fees
2 Sept - 3 Sept
Hilton Garden Inn Annapolis

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (412)
"Great location and amenities"
The price is S$355
includes taxes & fees
1 Sept - 2 Sept
The Inn at Chesapeake Bay Beach Club

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (111)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is S$281
includes taxes & fees
25 Aug - 26 Aug
Kent Island Resort

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1002)
"Great place and great staff "
The price is S$159
includes taxes & fees
14 Sept - 15 Sept
Courtyard by Marriott Annapolis

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (856)
"Great location and staff! The hotel is nice - wish that they had a bar and restaurant on site but plenty of options within walking distance though. Nice view of the water and updated rooms."
The price is S$346
includes taxes & fees
1 Sept - 2 Sept
Annapolis Waterfront Hotel, Autograph Collection

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1816)
"Great stay"
Historic Inns of Annapolis

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (62)
"Good service and good options to enjoy the stays. "
The price is S$295
includes taxes & fees
18 Sept - 19 Sept
Wylder Tilghman Island

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1009)
"Clean nice and breakfast was included which was a plus. Staff was very nice. "
The price is S$148
includes taxes & fees
1 Sept - 2 Sept
Country Inn & Suites by Radisson, Annapolis, MD

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1001)
"Nice hotel, convenient location with easy parking. "
The price is S$145
includes taxes & fees
31 Aug - 1 Sept
DoubleTree by Hilton Hotel Annapolis

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (863)
"Great room for a great price... Very friendly staff, too."
The price is S$143
includes taxes & fees
25 Aug - 26 Aug
Sonesta ES Suites Annapolis

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Great place"
The price is S$154
includes taxes & fees
28 Aug - 29 Aug
SpringHill Suites by Marriott Annapolis

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (102)
"Beautiful location on the water. The staff are super nice and helpful. The restaurant is very good. We had an excellent house smoked pulled pork sandwich and a shrimp po boy."
The price is S$289
includes taxes & fees
26 Aug - 27 Aug
The Tilghman Island Inn

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1001)
"Great staff….property a bit “tired” but a very friendly staff working hard to make it comfortable. A decent value for location and price!"
The price is S$158
includes taxes & fees
25 Aug - 26 Aug
Holiday Inn Express & Suites Annapolis by IHG

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very good, (1004)
"Very nice stay. Front desk staff was friendly and the pool is a great bonus."
The price is S$156
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn & Suites Annapolis

Sandaway Suites & Beach

3.0 star property
9.4 out of 10, Exceptional, (148)
"Excellent hospitality. Also the property is in a good location with great water views."
The price is S$408
includes taxes & fees
25 Aug - 26 Aug
Sandaway Suites & Beach

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (135)
"complimentry breakfast is good ,friendly staff,clean and quite "
The price is S$197
includes taxes & fees
28 Aug - 29 Aug
Fairfield Inn & Suites By Marriott 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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Learn more about Chester

Chester awaits: its island views, sunny weather, golf and more!

Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel 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 Graduate by Hilton Annapolis and Country Inn & Suites by Radisson, Annapolis, MD. 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?

Country Inn & Suites by Radisson, Annapolis, MD: Features buffet, an indoor pool and free self parking. Sonesta ES Suites Annapolis and Crowne Plaza Annapolis by IHG 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 16 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 Matapeake State Park, Chesapeake Bay Environmental Center 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.