Photo by Patricia Knorr

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Compare 1,202 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Our top choices for Chester hotels

St Michaels Inn
Front of property

St Michaels Inn

2.5 star property
8.2 out of 10, Very Good, (1001)
"Great place to stay"
The price is ₩132,802
₩146,084 total
includes taxes & fees
Oct 1 - Oct 2
St Michaels Inn
Inn at Haven Harbour
View from property

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 ₩259,263
₩346,593 total
includes taxes & fees
Sep 25 - Sep 26
Inn at Haven Harbour
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (896)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is ₩176,995
₩196,465 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Inn Express Annapolis East-Kent Island by IHG
Quality Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
7.8 out of 10, Good, (827)
"Great place and great staff"
The price is ₩136,188
₩151,168 total
includes taxes & fees
Sep 17 - Sep 18
Quality Inn
Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (90)
"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 ₩216,366
₩240,170 total
includes taxes & fees
Sep 15 - Sep 16
Mariners Motel
The Wildset
Premium Room | Frette Italian sheets, premium bedding, iron/ironing board, free WiFi

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (375)
"Super cute hotel…….very clean and walkable to everything."
The price is ₩305,212
₩366,394 total
includes taxes & fees
Oct 13 - Oct 14
The Wildset
Quality Inn
Exterior

Quality Inn

2.5 star property
7.6 out of 10, Good, (788)
"Always look forward to our stay here on our way to the ocean. It’s part of our yearly plan. "
The price is ₩118,461
₩130,308 total
includes taxes & fees
Oct 1 - Oct 2
Quality Inn
The Tidewater Inn
Terrace/patio

The Tidewater Inn

3.0 star property
8.8 out of 10, Excellent, (827)
"Great place - our third stay!"
The price is ₩277,338
₩305,072 total
includes taxes & fees
Sep 15 - Sep 16
The Tidewater Inn
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very Good, (1003)
"Excellent location"
The price is ₩176,186
₩195,566 total
includes taxes & fees
Sep 21 - Sep 22
Best Western Kent Narrows Inn
Fairfield Inn & Suites by Marriott Easton
View from property

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (360)
"Absolutely amazing staff! Nicest hotel ive ever been in!"
The price is ₩224,379
₩246,817 total
includes taxes & fees
Oct 5 - Oct 6
Fairfield Inn & Suites by Marriott Easton
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (53)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
The price is ₩223,362
₩247,932 total
includes taxes & fees
Sep 29 - Sep 30
Inn at Huntingfield Creek
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (417)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is ₩313,574
₩383,523 total
includes taxes & fees
Oct 1 - Oct 2
The Inn at Chesapeake Bay Beach Club
Anchored Inn at Hidden Harbour Marina
Front of property

Anchored Inn at Hidden Harbour Marina

2.5 star property
9.4 out of 10, Exceptional, (450)
"The staff specifically Victoria was impeccable! "
The price is ₩249,604
₩284,549 total
includes taxes & fees
Sep 17 - Sep 18
Anchored Inn at Hidden Harbour Marina
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.8 out of 10, Excellent, (75)
"Very relaxing stay."
The price is ₩236,057
₩320,984 total
includes taxes & fees
Sep 21 - Sep 22
Wylder Tilghman Island
Best Western Plus Easton Inn & Suites
Lobby

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1005)
"Nice comfortable stay."
The price is ₩193,719
₩213,091 total
includes taxes & fees
Sep 15 - Sep 16
Best Western Plus Easton Inn & Suites
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (113)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is ₩237,062
₩314,430 total
includes taxes & fees
Sep 24 - Sep 25
Kent Island Resort
Hampton Inn Easton
Exterior

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (535)
"I’ve been travel for so many locations but this hotel was the best place I ever had so far staffing very politely and friendly and the free breakfast deserves my best appreciation. "
The price is ₩195,461
₩215,007 total
includes taxes & fees
Sep 28 - Sep 29
Hampton Inn Easton
The Tilghman Island Inn
Outdoor banquet area

The Tilghman Island Inn

3.5 star property
9.6 out of 10, Exceptional, (109)
"Great staff and food!"
The price is ₩285,700
₩314,270 total
includes taxes & fees
Sep 17 - Sep 18
The Tilghman Island Inn
Laurel Grove Inn on the South
Outdoor dining

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (524)
"Great location with fantastic views. Very friendly owner "
The price is ₩250,859
₩285,979 total
includes taxes & fees
Sep 18 - Sep 19
Laurel Grove Inn on the South
SpringHill Suites by Marriott Annapolis
Free daily self-serve breakfast

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Clean room, Good breakfast and friendly staff."
The price is ₩158,738
₩180,961 total
includes taxes & fees
Sep 28 - Sep 29
SpringHill Suites by Marriott Annapolis
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
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Staff was great. Clean room. "
Lindsay 2-night trip
Posted 7 days ago
Crowne Plaza Annapolis by IHG

More cheap stays in Chester

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd, Annapolis, MD
The price is ₩102,852 per night from Oct 7 to Oct 8
₩102,852
₩117,251 total
Oct 7 - Oct 8
includes taxes & fees

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Country Inn & Suites by Radisson, Annapolis, MD and Sonesta ES Suites 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: Offers 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.