Photo by Patricia Knorr

Find hotels in Chester, MD from ฿2,469

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Top 10 Chester hotels and places to stay

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (362)
"Fantastic place for a couple getaway. "
The price is ฿7,280
฿8,723 total
includes taxes & fees
27 Aug - 28 Aug
The Wildset

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (77)
"Hummingbird Inn is so gracious to all guests. I was there for a triathlon and Eric and Mary made sure I was taken care of to race! Love this Inn!"
Hummingbird Inn

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 ฿5,043
฿5,598 total
includes taxes & fees
27 Aug - 28 Aug
Mariners Motel

The Tidewater Inn

3.0 star property
8.8 out of 10, Excellent, (819)
"Very nice hotel and area. Would stay again. "
The price is ฿5,815
฿6,396 total
includes taxes & fees
27 Aug - 28 Aug
The Tidewater Inn

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Nice comfortable stay."
The price is ฿4,181
฿4,599 total
includes taxes & fees
31 Aug - 1 Sept
Best Western Plus Easton Inn & Suites

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (36)
"The facility designed was out standing and the staff was very good. "
The price is ฿13,420
฿14,762 total
includes taxes & fees
31 Aug - 1 Sept
The Oaks Waterfront

Quality Inn

2.5 star property
7.6 out of 10, Good, (777)
"Comfortable and reasonably priced we stay at this clean hotel when we are here in this area. "
The price is ฿3,010
฿3,311 total
includes taxes & fees
1 Sept - 2 Sept
Quality Inn

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (130)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is ฿7,439
฿8,183 total
includes taxes & fees
27 Aug - 28 Aug
Parsonage Inn

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very good, (3)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
The price is ฿6,803
฿8,273 total
includes taxes & fees
27 Aug - 28 Aug
Inn at Haven Harbour

Quality Inn

2.5 star property
7.8 out of 10, Good, (816)
"Conveniently located with overall great value."
The price is ฿3,174
฿3,524 total
includes taxes & fees
17 Sept - 18 Sept
Quality Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (894)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is ฿4,385
฿4,868 total
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (103)
"So friendly and professional service!"
The price is ฿6,659
฿7,325 total
includes taxes & fees
27 Aug - 28 Aug
The Tilghman Island Inn

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (520)
"Beautiful property and lovely hosts."
The price is ฿5,847
฿6,666 total
includes taxes & fees
25 Sept - 26 Sept
Laurel Grove Inn on the South

Sandaway Suites & Beach

3.0 star property
9.4 out of 10, Exceptional, (149)
"Excellent hospitality. Also the property is in a good location with great water views."
The price is ฿9,405
฿10,346 total
includes taxes & fees
28 Aug - 29 Aug
Sandaway Suites & Beach

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is ฿7,309
฿8,040 total
includes taxes & fees
27 Aug - 28 Aug
George Brooks House B&B

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (358)
"Great place! "
The price is ฿4,938
฿5,431 total
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites by Marriott Easton

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (340)
"Our room overlooked the channel at Knapp's Narrows. The staff is friendly and helpful. We will definitely stay here again."
The price is ฿7,147
฿7,861 total
includes taxes & fees
31 Aug - 1 Sept
Knapps Narrows Marina & Inn

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (867)
"Great room for a great price... Very friendly staff, too."
The price is ฿3,216
฿3,666 total
includes taxes & fees
15 Sept - 16 Sept
Sonesta ES Suites Annapolis

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (64)
"Good service and good options to enjoy the stays. "
The price is ฿5,502
฿7,482 total
includes taxes & fees
18 Sept - 19 Sept
Wylder Tilghman Island

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (617)
"Great place to stay. "
The price is ฿5,198
฿5,769 total
includes taxes & fees
22 Sept - 23 Sept
Hyatt Place Kent Narrows & Marina
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

More cheap stays in Chester

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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.