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

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Oct 30 - Nov 1
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Nov 6 - Nov 8

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Our top choices for Chester hotels

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

1. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (851 reviews)
"Awesome place"
United States
Joseph
The price is ₩239,790
₩266,166 total
includes taxes & fees
Nov 1 - Nov 2
Hyatt Place Kent Narrows & Marina
Two Adirondack chairs facing a calm body of water with a clear sky above.

2. 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 ₩127,263
₩141,262 total
includes taxes & fees
Nov 29 - Nov 30
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.

3. 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 ₩260,126
₩322,676 total
includes taxes & fees
Dec 1 - Dec 2
The Inn at Chesapeake Bay Beach Club
A patio with outdoor seating, overlooking a marina with boats.

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)
"Had a good time. Nice area"
United States
Thomas E
The price is ₩169,648
₩188,310 total
includes taxes & fees
Nov 29 - Nov 30
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, (1,002 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 ₩119,898
₩133,087 total
includes taxes & fees
Nov 30 - Dec 1
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 ₩173,765
₩237,242 total
includes taxes & fees
Nov 29 - Nov 30
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 ₩111,777
₩124,073 total
includes taxes & fees
Nov 29 - Nov 30
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 ₩225,443
₩257,006 total
includes taxes & fees
Nov 23 - Nov 24
The Westin Annapolis
A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

9. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,060 reviews)
"Great location, excellent stay"
United States
Christiaan
The price is ₩114,296
₩175,920 total
includes taxes & fees
Dec 1 - Dec 2
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, (1,264 reviews)
"Excellent staff & service!"
United States
Michele
The price is ₩119,734
₩136,497 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, (1,000 reviews)
"Brunch was the best we had the whole trip! Excellent food and wonderful staff."
United States
REBECCA
The price is ₩173,924
₩198,273 total
includes taxes & fees
Nov 29 - Nov 30
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, (1,000 reviews)
"Great location"
United States
Jose
The price is ₩135,301
₩154,243 total
includes taxes & fees
Nov 10 - Nov 11
Crowne Plaza Annapolis by IHG
Lobby

13. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,000 reviews)
"Great location, friendly staff."
United States
Joel
The price is ₩128,182
₩146,128 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Garden Inn Annapolis Downtown
A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

14. 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 don’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 ₩673,015
₩740,317 total
includes taxes & fees
Nov 23 - Nov 24
Inn at Perry Cabin
A balcony with a table set for two, overlooking a marina with boats.

15. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,000 reviews)
"Easy access to downtown, Great waterside restaurants."
United States
John
The price is ₩297,744
₩339,428 total
includes taxes & fees
Nov 29 - Nov 30
Annapolis Waterfront Hotel, Autograph Collection
An indoor swimming pool with lounge chairs and a no diving sign.

16. Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (639 reviews)
"would go again"
United States
Alison
The price is ₩179,508
₩197,459 total
includes taxes & fees
Nov 29 - Nov 30
Holiday Inn Express Easton by IHG
A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

17. The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (936 reviews)
"We had a wonderful stay and thoroughly enjoyed our time in Easton!"
United States
Miriam
The price is ₩238,782
₩262,660 total
includes taxes & fees
Nov 22 - Nov 23
The Tidewater Inn
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.

18. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (394 reviews)
"Love this hotel, everyone was friendly and it was so clean! I’m really picky about where I stay and I would absolutely stay here again."
United States
Amanda
The price is ₩169,662
₩186,628 total
includes taxes & fees
Nov 5 - Nov 6
Fairfield Inn & Suites by Marriott Easton
A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

19. 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 ₩165,414
₩188,572 total
includes taxes & fees
Nov 29 - Nov 30
SpringHill Suites by Marriott Annapolis
A two-story house with a porch, a front door, and a small garden area.

20. The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (524 reviews)
"Great stay in St. Michael’s! Room was clean and comfortable. The staff were all friendly and helpful. The included continental breakfast was delicious and convenient. The bar and restaurant were fabulous!"
United States
Jennifer
The price is ₩265,462
₩325,358 total
includes taxes & fees
Dec 1 - Dec 2
The Wildset
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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Great place to stay"
Michael 2-night trip
Posted 2 hours ago
Hyatt Place Kent Narrows & Marina

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
The price is ₩95,260 per night from Nov 22 to Nov 23
₩95,260
₩108,596 total
Nov 22 - Nov 23
includes taxes & fees

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 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches.