Photo by Patricia Knorr

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Top 10 trending Chester hotels

Holiday Inn Express Annapolis East-Kent Island by IHG
Welcome to the Holiday Inn Express, where guests can check in and enjoy a convenient stay.

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (878)
"Great stay beautiful view"
The price is €121
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Hyatt Place Kent Narrows & Marina
Relax by the fire pit in this scenic waterfront seating area, overlooking the marina with boats docked.

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (603)
"Great place to stay. "
The price is €158
includes taxes & fees
21 Aug - 22 Aug
Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Kent Island Marina
Relax on the outdoor terrace with a view of the marina, surrounded by wicker furniture and beautiful flowers.

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (980)
"Friendly staff, nice environment"
The price is €146
includes taxes & fees
17 Aug - 18 Aug
Hilton Garden Inn Kent Island Marina
The Westin Annapolis
Experience the grandeur of this classic hotel, featuring a symmetrical facade with a central entrance and evenly spaced windows.

The Westin Annapolis

4.0 star property
8.6 out of 10, Excellent, (1001)
"The Hotel was very clean and convenient to everything that we wanted to do!!!!"
The price is €155
includes taxes & fees
24 Aug - 25 Aug
The Westin Annapolis
Hilton Garden Inn Annapolis
Relax in this stylish room with two beds, a desk, and a flat-screen TV.

Hilton Garden Inn Annapolis

3.0 star property
8.2 out of 10, Very good, (1001)
"Great staff! Super clean."
The price is €93
includes taxes & fees
13 Aug - 14 Aug
Hilton Garden Inn Annapolis
The Inn at Chesapeake Bay Beach Club
Welcome to our hotel, featuring a modern entrance with a covered area and lush greenery.

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (406)
"Staff was very polite and friendly. "
The price is €217
includes taxes & fees
24 Aug - 25 Aug
The Inn at Chesapeake Bay Beach Club
Annapolis Waterfront Hotel, Autograph Collection
Relax in this serene room with a large bed, a comfortable armchair, and a floor lamp, offering a view of the nearby water.

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (852)
"Front desk staff was very friendly and helpful."
The price is €232
includes taxes & fees
17 Aug - 18 Aug
Annapolis Waterfront Hotel, Autograph Collection
Historic Inns of Annapolis
Relax in the serene outdoor patio, surrounded by trees and equipped with comfortable seating and tables.

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1816)
"We’ve been here a few times and continue to to love the location, staff and comfortable beds. "
Historic Inns of Annapolis
Courtyard by Marriott Annapolis
Welcome to the Courtyard by Marriott, featuring a contemporary design and a covered entrance with a walkway leading to the main doors.

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1002)
"Great place and great staff "
The price is €103
includes taxes & fees
14 Aug - 15 Aug
Courtyard by Marriott Annapolis
Kent Island Resort
Surrounded by lush greenery and a serene lake, this historic property offers a picturesque setting with a spacious parking area and a circular driveway.

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (107)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is €193
includes taxes & fees
1 Sept - 2 Sept
Kent Island Resort
Wylder Tilghman Island
Relax by the serene pool surrounded by comfortable sun loungers and umbrellas, set in an and secure area.

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (59)
"Good service and good options to enjoy the stays. "
The price is €199
includes taxes & fees
18 Aug - 19 Aug
Wylder Tilghman Island
Hampton Inn & Suites Annapolis
Two single beds with white linens, a flat-screen TV, and a desk with a telephone.

Hampton Inn & Suites Annapolis

2.5 star property
8.2 out of 10, Very good, (1005)
"Very nice stay. Front desk staff was friendly and the pool is a great bonus."
The price is €99
includes taxes & fees
14 Aug - 15 Aug
Hampton Inn & Suites Annapolis
Country Inn & Suites by Radisson, Annapolis, MD
Two large beds with white linens and dark brown headboards, a desk with a lamp and chair, and a large window with curtains.

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Great visit "
The price is €95
includes taxes & fees
14 Aug - 15 Aug
Country Inn & Suites by Radisson, Annapolis, MD
SpringHill Suites by Marriott Annapolis
Fully equipped kitchen with dark cabinetry, white countertops, and modern appliances.

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1002)
"Room is spacious, great for families"
The price is €99
includes taxes & fees
24 Aug - 25 Aug
SpringHill Suites by Marriott Annapolis
Holiday Inn Express & Suites Annapolis by IHG
Indulge in a diverse selection of international cuisine at our buffet, featuring omelets, cheese, and more.

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1000)
"Bed was very comfortable "
The price is €91
includes taxes & fees
13 Aug - 14 Aug
Holiday Inn Express & Suites Annapolis by IHG
DoubleTree by Hilton Hotel Annapolis
Welcome to DoubleTree by Hilton, featuring a traditional brick facade and a distinctive peaked roof.

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1001)
"The Double Tree was a great place to stay! Great location amd the staff are very pleasant and helpful! "
The price is €96
includes taxes & fees
12 Aug - 13 Aug
DoubleTree by Hilton Hotel Annapolis
Sandaway Suites & Beach
Situated near a serene lake or sea, this two-story house offers a tranquil beachfront setting with a dock and lush surroundings.

Sandaway Suites & Beach

3.0 star property
9.4 out of 10, Exceptional, (144)
"Beautiful historic building and rooms. Scenic, quiet grounds, calming views of the bay. A true gem !"
The price is €273
includes taxes & fees
11 Aug - 12 Aug
Sandaway Suites & Beach
Sonesta ES Suites Annapolis
Relax in a spacious room with a large bed, desk, and sofa, offering a comfortable seating area and a view.

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (851)
"Great room for a great price... Very friendly staff, too."
The price is €96
includes taxes & fees
7 Sept - 8 Sept
Sonesta ES Suites Annapolis
The Tilghman Island Inn
Enjoy al fresco dining with a view of the water and a warm fire pit.

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (101)
"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 €193
includes taxes & fees
24 Aug - 25 Aug
The Tilghman Island Inn
Crowne Plaza Annapolis by IHG
Relax by the pool surrounded by lounge chairs and a skylight.

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1002)
"Very clean and friendly staff. Best mattress and pillows have had in hotel."
The price is €113
includes taxes & fees
28 Aug - 29 Aug
Crowne Plaza Annapolis by IHG
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!

See all hotels in Chester
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"This hotel is great. Good location accommodations are beautiful. The only thing they lack is a coffee maker in the room."
william 2-night trip
Posted 1 day ago
Graduate by Hilton Annapolis

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.

What are some of the best holiday rentals that Chester has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chester offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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?

Country Inn & Suites by Radisson, Annapolis, MD: Provides buffet, an indoor pool and free self parking. Sonesta ES Suites Annapolis and SpringHill Suites by Marriott 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 17 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.