A boat docked at a pier during twilight with a city skyline in the background.

Chester hotels from RM422

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Check prices for these dates

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

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Our top choices for Chester hotels

Lobby

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,006 reviews)
"Everything about this hotel was excellent and I would highly recommend staying here"
United States
David
The price is RM566
RM622 total
includes taxes & fees
1 Jul - 2 Jul
Best Western Plus Easton Inn & Suites
In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (927 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is RM407
RM452 total
includes taxes & fees
12 Jul - 13 Jul
Quality Inn Grasonville near Kent Island
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, (612 reviews)
"A clean hotel and a great breakfast."
United States
Maura
The price is RM586
RM645 total
includes taxes & fees
12 Jul - 13 Jul
Holiday Inn Express Easton by IHG
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (150 reviews)
"It was such a lovely quaint resort. I loved everything about staying there. Thank you."
United States
Sue
The price is RM640
RM849 total
includes taxes & fees
1 Jul - 2 Jul
Kent Island Resort
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Good hotel for the price"
United States
Brenda
The price is RM510
RM566 total
includes taxes & fees
5 Jul - 6 Jul
Best Western Kent Narrows Inn
Exterior

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (895 reviews)
"A good value."
United States
Alexander
The price is RM412
RM453 total
includes taxes & fees
22 Jul - 23 Jul
Quality Inn
Meeting facility

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (895 reviews)
"Loved everything about this beautiful hotel."
United States
Diane
The price is RM729
RM802 total
includes taxes & fees
5 Jul - 6 Jul
The Tidewater Inn
Front of property

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,000 reviews)
"Great location, modern rooms compared to area offerings."
United States
Shruti
The price is RM427
RM470 total
includes taxes & fees
12 Jul - 13 Jul
St Michaels Inn
Lobby lounge

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (378 reviews)
"Had a short stay in Easton to visit family. The hotel and staff were wonderful. Breakfast was decent. I would recommend this hotel and plan to stay here in future."
United States
Linda
The price is RM550
RM605 total
includes taxes & fees
12 Jul - 13 Jul
Fairfield Inn & Suites by Marriott Easton
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,020 reviews)
"The staff was great, nice hotel bar and the location was close to everything!"
United States
Diane
The price is RM388
RM442 total
includes taxes & fees
5 Jul - 6 Jul
DoubleTree by Hilton Hotel Annapolis
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (777 reviews)
"Great Stay!!"
United States
Richard
The price is RM766
RM850 total
includes taxes & fees
6 Jul - 7 Jul
Hyatt Place Kent Narrows & Marina
Front of property

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (490 reviews)
"absolutely perfect for this traveler!"
United States
BENNY
The price is RM986
RM1,124 total
includes taxes & fees
1 Jul - 2 Jul
Anchored Inn at Hidden Harbour Marina
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, (1,000 reviews)
"Beautiful view!!! Clean hotel and very nice helpful staff. Would stay again."
United States
Michele
The price is RM566
RM628 total
includes taxes & fees
20 Jul - 21 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1,000 reviews)
"The hotel was clean and looked nice, the bed was very soft in the middle and uncomfortable and the $14 breakfast was no where near worth it."
United States
Sandy
The price is RM631
RM700 total
includes taxes & fees
19 Jul - 20 Jul
Hilton Garden Inn Kent Island Marina
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, (393 reviews)
"Easy check in, clean and comfortable room. "
United States
michael
The price is RM366
RM403 total
includes taxes & fees
6 Jul - 7 Jul
Econo Lodge Easton Route 50
Bar (on property)

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (572 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 RM595
RM655 total
includes taxes & fees
19 Jul - 20 Jul
Hampton Inn Easton
Dining

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,010 reviews)
"Clean, reasonably priced , great staff and excellent breakfast!"
United States
Brian
The price is RM370
RM422 total
includes taxes & fees
5 Jul - 6 Jul
Best Western Annapolis
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, (1,045 reviews)
"Friendly staff, easy parking, great breakfast"
United States
Theresa
The price is RM446
RM509 total
includes taxes & fees
12 Jul - 13 Jul
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, (467 reviews)
"Wonderful stay!"
United States
Rachel
The price is RM1,014
RM1,205 total
includes taxes & fees
28 Jul - 29 Jul
The Wildset
Property grounds

Sandaway Suites & Beach

Sandaway Suites & Beach
3.0 star property
Oxford
9.4 out of 10, Exceptional, (173 reviews)
"It was a beautiful stay!"
United States
Eliza
The price is RM710
RM780 total
includes taxes & fees
28 Jul - 29 Jul
Sandaway Suites & Beach
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
A boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

The Wildset

The Wildset

10/10 Excellent
"The Wildset is extremely walkable to downtown Saint Michaelā€™s and the Chesapeake Bay Maritime Museum. The grounds are charming and the evening sā€™mores were delicious. The staff was attentive and friendly and our rooms were spotless and excellent"
Anne 2-night trip
Posted 2 hours ago
The Wildset

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is RM370 per night from 5 Jul to 6 Jul
RM370
RM422 total
5 Jul - 6 Jul
includes taxes & fees
7.8/10 Good! (1,010 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 Crowne Plaza Annapolis by IHG. 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 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?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. Country Inn & Suites by Radisson, Annapolis, MD and St Michaels Inn 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 Sandy Point Beach 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 23Ā°C, while the coldest months are January and February, with an average of 4Ā°C. Average annual precipitation for Chester is 1414 mm.

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