Photo by Patricia Knorr

Find hotels in Chester, MD from SAR 223

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28 Jun - 29 Jun
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29 Jun - 30 Jun
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4 Jul - 6 Jul
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11 Jul - 13 Jul

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Compare 1,242 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Wildset
Premium Room | 1 bedroom, Frette Italian sheets, premium bedding, iron/ironing board

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (329)
"The room was lovely - comfortable beds, it bathroom, nice toiletries. It’s quiet yet right in the center of town so you can walk to all the shops and restaurants. "
The price is SAR 821
SAR 986 total
includes taxes & fees
30 Jun - 1 Jul
The Wildset
Knapps Narrows Marina & Inn
Exterior

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (333)
"Extremely clean, wonderful place "
The price is SAR 675
SAR 743 total
includes taxes & fees
30 Jun - 1 Jul
Knapps Narrows Marina & Inn
Graduate by Hilton Annapolis
View from property

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1009)
"Loved our stay here, perfect place for an Annapolis weekend!"
The price is SAR 581
SAR 663 total
includes taxes & fees
6 Jul - 7 Jul
Graduate by Hilton Annapolis
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, (395)
"Beautiful place, quiet and clean. "
The price is SAR 806
SAR 990 total
includes taxes & fees
13 Jul - 14 Jul
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, (437)
"The staff specifically Victoria was impeccable! "
The price is SAR 908
SAR 1,035 total
includes taxes & fees
30 Jun - 1 Jul
Anchored Inn at Hidden Harbour Marina
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (128)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is SAR 975
SAR 1,073 total
includes taxes & fees
2 Jul - 3 Jul
Parsonage Inn
Mariners Motel
Outdoor pool

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 SAR 582
SAR 646 total
includes taxes & fees
30 Jun - 1 Jul
Mariners Motel
Hyatt Place Kent Narrows & Marina
Terrace/patio

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (566)
"Great place to stay. "
The price is SAR 649
SAR 720 total
includes taxes & fees
7 Jul - 8 Jul
Hyatt Place Kent Narrows & Marina
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very Good, (1000)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
The price is SAR 441
SAR 489 total
includes taxes & fees
30 Jun - 1 Jul
Best Western Kent Narrows Inn
DoubleTree by Hilton Hotel Annapolis
Lobby

DoubleTree by Hilton Hotel Annapolis

4.0 star property
8.6 out of 10, Excellent, (1002)
"best doubletree I have stayed in. "
The price is SAR 376
SAR 429 total
includes taxes & fees
14 Jul - 15 Jul
DoubleTree by Hilton Hotel Annapolis
Best Western Plus Easton Inn & Suites
Lobby

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1001)
"The property was in good shape. We had a good time and it was convenient to go anywhere. "
The price is SAR 484
SAR 532 total
includes taxes & fees
30 Jun - 1 Jul
Best Western Plus Easton Inn & Suites
Hilton Garden Inn Annapolis Downtown
Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV

Hilton Garden Inn Annapolis Downtown

3.0 star property
8.6 out of 10, Excellent, (1007)
"Hotel was clean, staff was friendly. Within walking distance of shops, restaurant and landmarks. "
The price is SAR 386
SAR 440 total
includes taxes & fees
21 Jul - 22 Jul
Hilton Garden Inn Annapolis Downtown
The Tidewater Inn
Terrace/patio

The Tidewater Inn

3.0 star property
8.8 out of 10, Excellent, (799)
"Nice place"
The price is SAR 634
SAR 697 total
includes taxes & fees
30 Jun - 1 Jul
The Tidewater Inn
Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1787)
"Wonderful stay!"
Historic Inns of Annapolis
TownePlace Suites by Marriott Annapolis
Exterior

TownePlace Suites by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (10)
"Everyone at the front desk was extremely friendly and helpful."
The price is SAR 379
SAR 432 total
includes taxes & fees
8 Jul - 9 Jul
TownePlace Suites by Marriott Annapolis
The Inn at Tacaro Estate
Horseback riding

The Inn at Tacaro Estate

5.0 star property
9.2 out of 10, Wonderful, (9)
"1940’s estate is maintained to remind you of those times. There was a “Speak-EZ” in the basement they had open Friday and Saturday evenings. My room was spacious and included a balcony. Huge front lawn with a pool and a view to the Bay. "
The Inn at Tacaro Estate
Country Inn & Suites by Radisson, Annapolis, MD
1 bedroom, hypo-allergenic bedding, desk, blackout drapes

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Great accommodations "
The price is SAR 379
SAR 432 total
includes taxes & fees
6 Jul - 7 Jul
Country Inn & Suites by Radisson, Annapolis, MD
134 Prince - Luxury Boutique Hotel
Front of property

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
Inn at Perry Cabin
Breakfast, lunch, dinner served; ocean views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (350)
"Grounds are beautiful. Staff very friendly and attentive "
The price is SAR 2,562
SAR 3,100 total
includes taxes & fees
6 Jul - 7 Jul
Inn at Perry Cabin
Kent Island Resort
Aerial view

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (103)
"It's only 20 min from the downtown annapolis.Clean too."
The price is SAR 1,159
SAR 1,445 total
includes taxes & fees
30 Jun - 1 Jul
Kent Island Resort
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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Family-friendly hotels in Chester you'll enjoy

Hampton Inn Easton
Exterior

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (513)
The price is SAR 561
SAR 617 total
includes taxes & fees
1 Jul - 2 Jul
Hampton Inn Easton

These apartments in Chester may fit your trip

First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (88)
The price is SAR 371
SAR 596 total
includes taxes & fees
1 Jul - 2 Jul
First Floor Studio Apartment in Historic Chestertown

Check out hotels with a water park in Chester

Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (73)
The price is SAR 1,013
SAR 1,856 total
includes taxes & fees
1 Jul - 2 Jul
Waterfront Oasis of Annapolis Star
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.

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

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 Hilton Garden Inn Annapolis Downtown 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: Provides 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 13 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.