Photo by Patricia Knorr

Find hotels in Chester, MD from ¥12,510

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Compare 1,247 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Our top choices for Chester hotels

Red Roof Inn Annapolis

2.0 star property
7.2 out of 10, Good, (381)
"I liked the landscaping, the greeting of the lobby staff upon check in, and 2 staff members in the lobby when checking out. The room was very nice and quiet. I am very pleased with this hotel. Thank you for making my stay great."
The price is ¥11,176
¥12,741 total
includes taxes & fees
Sep 3 - Sep 4
Red Roof Inn Annapolis

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (873)
"Great room for a great price... Very friendly staff, too."
The price is ¥16,638
¥18,968 total
includes taxes & fees
Sep 28 - Sep 29
Sonesta ES Suites Annapolis

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 ¥20,440
¥22,688 total
includes taxes & fees
Sep 14 - Sep 15
Holiday Inn Express Annapolis East-Kent Island by IHG

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1847)
"Excellent location, clean, friendly staff"
Historic Inns of Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1024)
"Nice location. "
The price is ¥14,874
¥16,956 total
includes taxes & fees
Sep 17 - Sep 18
Country Inn & Suites by Radisson, Annapolis, MD

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (139)
"Liked everything my stay was wonderful will be back "
The price is ¥22,352
¥25,482 total
includes taxes & fees
Sep 7 - Sep 8
Fairfield Inn & Suites By Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1010)
"Clean room, Good breakfast and friendly staff."
The price is ¥16,764
¥19,111 total
includes taxes & fees
Sep 15 - Sep 16
SpringHill Suites by Marriott Annapolis

Econo Lodge Easton Route 50

2.5 star property
6.6 out of 10, (373)
"The staff was VERY nice"
The price is ¥11,885
¥13,073 total
includes taxes & fees
Oct 1 - Oct 2
Econo Lodge Easton Route 50

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1014)
"Very nice property new rooms "
The price is ¥12,716
¥14,497 total
includes taxes & fees
Sep 11 - Sep 12
Best Western Annapolis

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (76)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
The price is ¥24,190
¥27,577 total
includes taxes & fees
Sep 3 - Sep 4
Flag House Inn

Hilton Garden Inn Annapolis Downtown

3.0 star property
8.6 out of 10, Excellent, (1012)
"Great Location "
The price is ¥16,028
¥18,271 total
includes taxes & fees
Sep 3 - Sep 4
Hilton Garden Inn Annapolis Downtown

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (67)
"Good service and good options to enjoy the stays. "
The price is ¥24,929
¥33,898 total
includes taxes & fees
Sep 18 - Sep 19
Wylder Tilghman Island

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 ¥30,439
¥33,483 total
includes taxes & fees
Sep 3 - Sep 4
George Brooks House B&B

Quality Inn

2.5 star property
7.6 out of 10, Good, (779)
"Always look forward to our stay here on our way to the ocean. It’s part of our yearly plan. "
The price is ¥12,510
¥13,760 total
includes taxes & fees
Oct 1 - Oct 2
Quality Inn

TownePlace Suites by Marriott Annapolis

3.0 star property
8.8 out of 10, Excellent, (15)
"very clean, and quiet, we are very comfortable with our stay with TownePlace Suites by Marriott Annapolis. Staff were friendly and we have a great check in."
The price is ¥16,176
¥18,440 total
includes taxes & fees
Sep 17 - Sep 18
TownePlace Suites by Marriott Annapolis

Village Inn

2.0 star property
6.2 out of 10, (493)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is ¥14,122
¥16,098 total
includes taxes & fees
Sep 3 - Sep 4
Village Inn

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (619)
"Great location"
The price is ¥23,381
¥25,953 total
includes taxes & fees
Sep 14 - Sep 15
Hyatt Place Kent Narrows & Marina

Residence Inn By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (45)
"It was close to the Stadium."
The price is ¥24,851
¥28,330 total
includes taxes & fees
Sep 3 - Sep 4
Residence Inn By Marriott Annapolis

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (79)
"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 ¥22,830
¥25,342 total
includes taxes & fees
Sep 3 - Sep 4
Mariners Motel
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!

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

More cheap stays in Chester

More cheap stays in Chester

Explore a world of travel with Expedia

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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 traveler data. Other good choices for your visit to 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's the top vacation rental in Chester?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: Visitors like this Chester vacation home rental. It offers a balcony, a garden, and a barbecue grill 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 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 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. Sonesta ES Suites Annapolis and The Westin 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.