Photo by Patricia Knorr

Find hotels in Chester, MD from CA $106

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Compare 1,243 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Our top choices for Chester hotels

Econo Lodge Easton Route 50

2.5 star property
6.6 out of 10, (372)
"The staff was VERY nice"
The price is CA $112
CA $123 total
includes taxes & fees
Sep 21 - Sep 22
Econo Lodge Easton Route 50

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (528)
"Check in staff is very helpful"
The price is CA $194
CA $214 total
includes taxes & fees
Aug 28 - Aug 29
Hampton Inn Easton

Quality Inn

2.5 star property
7.6 out of 10, Good, (773)
"Comfortable and reasonably priced we stay at this clean hotel when we are here in this area. "
The price is CA $128
CA $141 total
includes taxes & fees
Aug 28 - Aug 29
Quality Inn

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1004)
"Nice comfortable stay."
The price is CA $179
CA $197 total
includes taxes & fees
Aug 25 - Aug 26
Best Western Plus Easton Inn & Suites

Holiday Inn Express Easton by IHG

3.0 star property
9.0 out of 10, Wonderful, (585)
"Friendly and efficient staff, and very clean accommodations."
The price is CA $223
CA $246 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Express Easton by IHG

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (357)
"Great place! "
The price is CA $211
CA $232 total
includes taxes & fees
Aug 28 - Aug 29
Fairfield Inn & Suites by Marriott Easton

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!"
The price is CA $391
CA $430 total
includes taxes & fees
Aug 24 - Aug 25
Hummingbird Inn

The Tidewater Inn

3.0 star property
8.8 out of 10, Excellent, (817)
"Very nice hotel and area. Would stay again. "
The price is CA $262
CA $288 total
includes taxes & fees
Aug 25 - Aug 26
The Tidewater Inn

Sandaway Suites & Beach

3.0 star property
9.4 out of 10, Exceptional, (146)
"Beautiful historic building and rooms. Scenic, quiet grounds, calming views of the bay. A true gem !"
The price is CA $401
CA $442 total
includes taxes & fees
Aug 26 - Aug 27
Sandaway Suites & Beach

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (34)
"The facility designed was out standing and the staff was very good. "
The price is CA $573
CA $630 total
includes taxes & fees
Aug 25 - Aug 26
The Oaks Waterfront

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1002)
"Very nice stay"
The price is CA $138
CA $152 total
includes taxes & fees
Sep 1 - Sep 2
St Michaels Inn

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (361)
"Fantastic place for a couple getaway. "
The price is CA $298
CA $359 total
includes taxes & fees
Aug 26 - Aug 27
The Wildset

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (359)
"Beautiful place to stay."
The price is CA $792
CA $959 total
includes taxes & fees
Sep 17 - Sep 18
Inn at Perry Cabin

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 CA $318
CA $349 total
includes taxes & fees
Aug 25 - Aug 26
Parsonage Inn

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 CA $287
CA $316 total
includes taxes & fees
Aug 25 - Aug 26
George Brooks House B&B

Quality Inn

2.5 star property
7.8 out of 10, Good, (813)
"Conveniently located with overall great value."
The price is CA $135
CA $150 total
includes taxes & fees
Sep 14 - Sep 15
Quality Inn

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (986)
"How clean and polite the staff was "
The price is CA $211
CA $234 total
includes taxes & fees
Aug 25 - Aug 26
Hilton Garden Inn Kent Island Marina

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 CA $182
CA $202 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Excellent location"
The price is CA $151
CA $167 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (612)
"Great place to stay. "
The price is CA $232
CA $257 total
includes taxes & fees
Aug 27 - Aug 28
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

Stay near popular Chester attractions

Chesapeake Exploration Center

Chesapeake Exploration Center

Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.

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 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.