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Aug 5 - Aug 6
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Top 10 trending Chester hotels

Best Western Kent Narrows Inn
Two single beds with white linens and dark wood headboard, flat-screen TV, and a dresser with drawers.

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very Good, (1006)
"A remarkable weekend getaway "
The price is P6,240
P6,927 total
includes taxes & fees
Aug 12 - Aug 13
Best Western Kent Narrows Inn
Quality Inn
Relax in a comfortable seating area with a sofa and armchairs, and enjoy a view of the outside from the large window.

Quality Inn

2.5 star property
7.8 out of 10, Good, (798)
"Conveniently located with overall great value."
The price is P5,363
P5,953 total
includes taxes & fees
Aug 6 - Aug 7
Quality Inn
Quality Inn
Stunning building with a brick and glass facade, featuring large windows and a flat roof, set amidst a beautifully manicured lawn with flowering bushes.

Quality Inn

2.5 star property
7.6 out of 10, Good, (761)
"Comfortable and reasonably priced we stay at this clean hotel when we are here in this area. "
The price is P5,315
P5,846 total
includes taxes & fees
Aug 12 - Aug 13
Quality Inn
St Michaels Inn
Stately building with a covered entrance and porch, set amidst a well-manicured lawn.

St Michaels Inn

2.5 star property
8.2 out of 10, Very Good, (1000)
"Great spot to be close to town for a modest price. "
The price is P5,770
P6,347 total
includes taxes & fees
Sep 1 - Sep 2
St Michaels Inn
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
10.0 out of 10, Exceptional, (1)
"We recently had the pleasure of staying at the Inn at Haven Harbour, specifically at their south location, and can't say enough good things about our experience! From the moment we arrived, we were captivated by the immaculate property and stunning surroundings. The views of the water were breathtaking, and having access to a private beach made our stay feel even more special. The amenities were top-notch, with a pool available for those who prefer a swim to the beach. The staff were incredibly...
The price is P12,014
P14,483 total
includes taxes & fees
Aug 12 - Aug 13
Inn at Haven Harbour
Fairfield Inn & Suites by Marriott Easton
Experience the warm welcome at this hotel, featuring a modern design with a brick and white exterior, a covered parking area and convenient entrance.

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (355)
"Very nice stay"
The price is P8,608
P9,469 total
includes taxes & fees
Aug 10 - Aug 11
Fairfield Inn & Suites by Marriott Easton
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, (404)
"Staff was very polite and friendly. "
The price is P11,760
P14,513 total
includes taxes & fees
Aug 24 - Aug 25
The Inn at Chesapeake Bay Beach Club
The Tidewater Inn
Enjoy wine tastings and gatherings in this elegant corridor with tables and chairs, featuring a dedicated wine room.

The Tidewater Inn

3.0 star property
8.8 out of 10, Excellent, (812)
"Very nice hotel and area. Would stay again. "
The price is P10,411
P11,453 total
includes taxes & fees
Aug 10 - Aug 11
The Tidewater Inn
Best Western Plus Easton Inn & Suites
Relax in this elegantly furnished living area with a plush sofa, ornate mirror, and stone fireplace.

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1005)
"Nice comfortable stay."
The price is P7,400
P8,140 total
includes taxes & fees
Aug 12 - Aug 13
Best Western Plus Easton Inn & Suites
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, (57)
"Good service and good options to enjoy the stays. "
The price is P9,810
P13,315 total
includes taxes & fees
Sep 1 - Sep 2
Wylder Tilghman Island
The Wildset
Relax in a spacious room with a large bed and sliding glass door leading to a balcony with a view.

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (350)
"This is where we stay everytime we come to St. Michaels - Top Knotch!"
The price is P11,307
P13,700 total
includes taxes & fees
Aug 19 - Aug 20
The Wildset
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 P7,974
P8,851 total
includes taxes & fees
Aug 12 - Aug 13
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Annapolis
Welcome to Best Western, where a warm entrance awaits, flanked by lush greenery.

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1007)
"It was very nice I will go there again"
The price is P4,802
P5,474 total
includes taxes & fees
Aug 10 - Aug 11
Best Western 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, (1006)
"Bed was very comfortable "
The price is P5,409
P6,167 total
includes taxes & fees
Aug 13 - Aug 14
Holiday Inn Express & Suites Annapolis by IHG
Mariners Motel
Docked in the marina, a sleek yacht awaits your arrival.

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is P8,906
P9,886 total
includes taxes & fees
Aug 12 - Aug 13
Mariners Motel
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, (1008)
"One of the nicest rooms I have ever stayed in at a chain hotel. I will definitely stay here again. "
The price is P5,803
P6,615 total
includes taxes & fees
Aug 24 - Aug 25
SpringHill Suites by Marriott Annapolis
Inn at Huntingfield Creek
Relax on the lakeside deck with a comfortable lounge chair, surrounded by lush greenery.

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek
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 P8,781
P11,819 total
includes taxes & fees
Sep 3 - Sep 4
Kent Island Resort
Anchored Inn at Hidden Harbour Marina
Stunning hotel with a symmetrical facade and landscaped gardens.

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (440)
"The staff specifically Victoria was impeccable! "
The price is P10,274
P11,713 total
includes taxes & fees
Sep 1 - Sep 2
Anchored Inn at Hidden Harbour Marina
134 Prince - Luxury Boutique Hotel
Stately two-story building with a welcoming entrance and beautifully maintained garden.

134 Prince - Luxury Boutique Hotel

2.5 star property
9.6 out of 10, Exceptional, (20)
"Great boutique hotel for an overnight. Terrific location and accommodating staff. Couldn't have been a better stay. "
134 Prince - Luxury Boutique Hotel
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Great visit "
Chris 6-night trip
Posted 17 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

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 traveler data. Other good choices for your visit to the area are Graduate by Hilton Annapolis and DoubleTree by Hilton Hotel 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 room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

Where can I learn more about changing or cancelling my trip to Chester?

To find more details about rescheduling or cancelling your trip to Chester, head over to our customer service page.

What are some accommodations with pools in Chester?

Country Inn & Suites by Radisson, Annapolis, MD: Features buffet, an indoor pool, and free self parking. Best Western Annapolis and SpringHill Suites by Marriott Annapolis are a couple of other choices with an onsite 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 accommodations 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. Check out what more 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches.