A coastal town with a marina, a bridge, and a highway.

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Oct 30 - Nov 1
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Our top choices for Chester hotels

A gazebo with a view of a lake at dusk.

1. 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)
"A wonderful stay! Already planning a trip for next year!"
United States
Michelle
The price is ā‚©139,186
ā‚©154,496 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Express Annapolis East-Kent Island by IHG
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

2. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (505 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is ā‚©283,447
ā‚©348,348 total
includes taxes & fees
Nov 15 - Nov 16
The Inn at Chesapeake Bay Beach Club
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (847 reviews)
"Awesome place"
United States
Joseph
The price is ā‚©184,531
ā‚©204,829 total
includes taxes & fees
Nov 24 - Nov 25
Hyatt Place Kent Narrows & Marina
A balcony with a view of a body of water, a row of buildings, and a chair.

4. 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)
"Great bartender she was a true professional at her job"
United States
Charles
The price is ā‚©173,087
ā‚©192,127 total
includes taxes & fees
Nov 24 - Nov 25
Hilton Garden Inn Kent Island Marina
A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.

5. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,001 reviews)
"We were in town for a wedding. The hotel was close to the venue which is why we chose it. The staff was very friendly upon check in, the room was very clean, nice bathroom, comfortable bed and the view of the bay from our room was fabulous! The included breakfast was the standard breakfast items but very good!"
United States
Beth
The price is ā‚©119,143
ā‚©132,248 total
includes taxes & fees
Nov 9 - Nov 10
Best Western Kent Narrows Inn
A large, two-story barn-style building with a covered front porch and a garage.

6. Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (188 reviews)
"Just a wonderful place, we had an amazing stay!"
United States
Bethany
The price is ā‚©162,443
ā‚©224,200 total
includes taxes & fees
Nov 17 - Nov 18
Kent Island Resort
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

7. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (1,000 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
The price is ā‚©110,872
ā‚©123,067 total
includes taxes & fees
Nov 22 - Nov 23
Quality Inn Grasonville near Kent Island
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

8. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,000 reviews)
"This is a fabulous resort! Very clean, great location and the staff is great!"
United States
Bobbi
The price is ā‚©224,023
ā‚©255,387 total
includes taxes & fees
Nov 22 - Nov 23
The Westin Annapolis
A historic brick building with a corner turret and multiple windows, located on a city street with flags and street lamps.

9. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,065 reviews)
"Great location, excellent stay"
United States
Christiaan
The price is ā‚©113,575
ā‚©174,811 total
includes taxes & fees
Nov 9 - Nov 10
Historic Inns of Annapolis
A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

10. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,265 reviews)
"Excellent staff & service!"
United States
Michele
The price is ā‚©118,480
ā‚©135,067 total
includes taxes & fees
Nov 10 - Nov 11
DoubleTree by Hilton Hotel Annapolis
A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

11. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,013 reviews)
"A great place to stay for a visit to USNA. It has a great vibe and is very convenient."
United States
Kathleen
The price is ā‚©183,699
ā‚©209,417 total
includes taxes & fees
Nov 22 - Nov 23
Graduate by Hilton Annapolis
A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.

12. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,006 reviews)
"Great location"
United States
Jose
The price is ā‚©133,884
ā‚©152,628 total
includes taxes & fees
Nov 10 - Nov 11
Crowne Plaza Annapolis by IHG
A balcony with a table set for two, overlooking a marina with boats.

13. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,003 reviews)
"Easy access to downtown, Great waterside restaurants."
United States
John
The price is ā‚©285,265
ā‚©325,202 total
includes taxes & fees
Nov 8 - Nov 9
Annapolis Waterfront Hotel, Autograph Collection
Lobby

14. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,012 reviews)
"Great location, friendly staff."
United States
Joel
The price is ā‚©122,828
ā‚©140,023 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Garden Inn Annapolis Downtown
A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

15. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (393 reviews)
"Love this hotel, everyone was friendly and it was so clean! Iā€™m really picky about where I stay and I would absolutely stay here again."
United States
Amanda
The price is ā‚©179,152
ā‚©197,067 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Easton
A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

16. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,003 reviews)
"The hotel is close to lots of shopping and dining options."
United States
FRANK
The price is ā‚©164,372
ā‚©187,384 total
includes taxes & fees
Nov 22 - Nov 23
SpringHill Suites by Marriott Annapolis
A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

17. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (407 reviews)
"Fantastic place; one of those that you donā€™t want to leave the property until the very sad time to go. Lovely staff, all of them, amazing food."
United States
Virgilio
The price is ā‚©642,267
ā‚©706,494 total
includes taxes & fees
Nov 11 - Nov 12
Inn at Perry Cabin
A hotel with a covered entrance, large columns, and a brick facade.

18. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.4 out of 10, Very good, (1,003 reviews)
"We stayed for 3 nights and we had a good experience."
Canada
Omer
The price is ā‚©116,651
ā‚©132,982 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Express & Suites Annapolis by IHG
A two-story house with a porch, a front door, and a small garden area.

19. The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (523 reviews)
"Room was clean and staff was super helpful and kind!"
United States
Sarah
The price is ā‚©304,011
ā‚©367,601 total
includes taxes & fees
Nov 9 - Nov 10
The Wildset
A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

20. The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (934 reviews)
"We had a wonderful stay and thoroughly enjoyed our time in Easton!"
United States
Miriam
The price is ā‚©237,279
ā‚©261,006 total
includes taxes & fees
Nov 1 - Nov 2
The Tidewater Inn
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 at 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 coastal town with a marina, a bridge, and a highway.

Top Chester Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"N/Aā€¦ā€¦ā€¦ā€¦ā€¦ā€¦ā€¦..,,,,,,,. Xxx. Cc"
William 2-night trip
Posted 4 hours ago
Historic Inns of Annapolis

Frequently asked questions

What's the best place to stay in Chester?
Located 13.8 mi (22.2 km) from the heart of Chester, DoubleTree by Hilton Hotel Annapolis is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Historic Inns of 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 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?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. St Michaels Inn and Sonesta ES Suites 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 9 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 Northern Chesapeake Bay, Matapeake State Park, and Eastern Neck National Wildlife Refuge. You'll also find Sandy Point Beach and Queenstown Harbor Golf 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 74Ā°F, while the coldest months are January and February with an average of 39Ā°F. Average annual precipitation for Chester is 56 inches.