Chester Hotels

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Check prices for these dates

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 Jun

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Our top choices for Chester hotels

Suite, 1 Queen Bed, Non Smoking

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (913 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is €101
includes taxes & fees
1 Jun - 2 Jun
Quality Inn Grasonville near Kent Island
Exterior

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (876 reviews)
"The staff was the best. Super nice and helpful."
United States
Christopher
The price is €95
includes taxes & fees
21 Jun - 22 Jun
Quality Inn
Lobby

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,001 reviews)
"Everything about this hotel was excellent and I would highly recommend staying here"
United States
David
The price is €131
includes taxes & fees
1 Jun - 2 Jun
Best Western Plus Easton Inn & Suites
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,005 reviews)
"Good hotel for the price"
United States
Brenda
The price is €110
includes taxes & fees
14 Jun - 15 Jun
Best Western Kent Narrows Inn
Front of property

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,002 reviews)
"We had a lovely stay and would go back again! Pleasant staff and a short ride to everything."
United States
JoAnn
The price is €128
includes taxes & fees
8 Jun - 9 Jun
St Michaels Inn
Desk, free WiFi, bed sheets

Econo Lodge Easton Route 50

Econo Lodge Easton Route 50
2.5 star property
Easton
6.6 out of 10, (392 reviews)
"Love overnight staff"
United States
Ivvory
The price is €76
includes taxes & fees
7 Jun - 8 Jun
Econo Lodge Easton Route 50
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,001 reviews)
"Great location and very clean!"
United States
Neille
The price is €128
includes taxes & fees
15 Jun - 16 Jun
Holiday Inn Express Annapolis East-Kent Island by IHG
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (141 reviews)
"We loved the quaintness of the room, complete with a gas fireplace and floor to ceiling drapes. Having a restaurant right on site was incredible. I especially loved the girl dinner deal! We enjoyed the stay and the property was beautiful."
United States
Kiana
The price is €176
includes taxes & fees
1 Jun - 2 Jun
Kent Island Resort
Meeting facility

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (882 reviews)
"Enjoyable stay great location!"
United States
Michelle
The price is €178
includes taxes & fees
1 Jun - 2 Jun
The Tidewater Inn
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,003 reviews)
"It was one of the nicest places we've stayed in our travels."
United States
William
The price is €118
includes taxes & fees
7 Jun - 8 Jun
DoubleTree by Hilton Hotel Annapolis
Exterior

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (383 reviews)
"Breakfast is excellent, staff very friendly"
United States
Polina
The price is €142
includes taxes & fees
1 Jun - 2 Jun
Knapps Narrows Marina & Inn
Lobby

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,020 reviews)
"Great location with good breakfast. 👍"
United States
David
The price is €95
includes taxes & fees
14 Jun - 15 Jun
Country Inn & Suites by Radisson, Annapolis, MD
Front of property

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (453 reviews)
"Wonderful stay!"
United States
Rachel
The price is €235
includes taxes & fees
8 Jun - 9 Jun
The Wildset
Bar (on property)

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (571 reviews)
"I have enjoyed Hampton Inns for years and this was no exception. The room and service were exceptional."
United States
Matthew
The price is €127
includes taxes & fees
7 Jun - 8 Jun
Hampton Inn Easton
Terrace/patio

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,001 reviews)
"Beautiful area"
United States
Dan
The price is €147
includes taxes & fees
15 Jun - 16 Jun
Hilton Garden Inn Kent Island Marina
Property grounds

Sandaway Suites & Beach

Sandaway Suites & Beach
3.0 star property
Oxford
9.4 out of 10, Exceptional, (165 reviews)
"It was a beautiful stay!"
United States
Eliza
The price is €202
includes taxes & fees
15 Jun - 16 Jun
Sandaway Suites & Beach
Free daily buffet breakfast

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (604 reviews)
"Very friendly and helpful staff."
United States
Andrew
The price is €145
includes taxes & fees
24 Jun - 25 Jun
Holiday Inn Express Easton by IHG
Lobby

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
9.0 out of 10, Wonderful, (258 reviews)
"Great stay in a quiet area"
United States
Mehran
The price is €95
includes taxes & fees
4 Jun - 5 Jun
Candlewood Suites Annapolis by IHG
Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is €170
includes taxes & fees
8 Jun - 9 Jun
Inn at Huntingfield Creek
Dining

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,002 reviews)
"Older Hotel but clean and staff was great."
United States
Gregory
The price is €81
includes taxes & fees
14 Jun - 15 Jun
Best Western 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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Stay near popular Chester attractions

Chesapeake Exploration Center

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

Learn more about Chester

Chester awaits: its island views, sunny weather, golf and more!

See all hotels in Chester
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
"Friendly staff"
Pravin 1-night trip
Posted 3 hours ago
Crowne Plaza Annapolis by IHG

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is €81 per night from 14 Jun to 15 Jun
€81
14 Jun - 15 Jun
includes taxes & fees
7.8/10 Good! (1,002 reviews)

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 DoubleTree by Hilton Hotel Annapolis and Sonesta ES Suites Annapolis. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Waterfront Sunset Bayview: sleeps 6: This highly rated holiday home rental in Chester is located on the waterfront, and offers a patio, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Our travellers also rate Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets! as a favourite home for rent in Chester. 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 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?
Sonesta ES Suites Annapolis: Offers buffet, a seasonal outdoor pool and complimentary wireless Internet access. Courtyard by Marriott 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 9 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 Northern Chesapeake Bay, Matapeake State Park and Chesapeake Bay Environmental Center. You'll also find Love Point State Park and Eastern Neck National Wildlife Refuge 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.

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