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

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Aug 30 - Aug 31
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Our top choices for Chester hotels

1. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
¥26,735
¥29,676 total
includes taxes & fees
Sep 8 - Sep 9
Hyatt Place Kent Narrows & Marina

2. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Betty
¥19,691
¥21,857 total
includes taxes & fees
Sep 28 - Sep 29
Holiday Inn Express Annapolis East-Kent Island by IHG

3. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
¥26,937
¥29,901 total
includes taxes & fees
Sep 1 - Sep 2
Hilton Garden Inn Kent Island Marina

4. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
Eliezer
¥18,623
¥20,672 total
includes taxes & fees
Sep 28 - Sep 29
Best Western Kent Narrows Inn

5. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
¥34,785
¥42,684 total
includes taxes & fees
Sep 28 - Sep 29
The Inn at Chesapeake Bay Beach Club

6. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
United States
Faezeh
¥16,009
¥17,769 total
includes taxes & fees
Sep 28 - Sep 29
Quality Inn Grasonville near Kent Island

7. Kent Island Resort

Kent Island Resort
Stevensville
United States
Margaret
¥25,907
¥34,208 total
includes taxes & fees
Sep 22 - Sep 23
Kent Island Resort

8. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
United States
Joshua
¥17,145
¥19,545 total
includes taxes & fees
Sep 13 - Sep 14
SpringHill Suites by Marriott Annapolis

9. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
United States
Heather
¥15,529
¥17,703 total
includes taxes & fees
Sep 13 - Sep 14
Crowne Plaza Annapolis by IHG

10. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
United States
Phyllis
¥15,369
¥17,521 total
includes taxes & fees
Sep 7 - Sep 8
Courtyard by Marriott Annapolis

11. St Michaels Inn

St Michaels Inn
St. Michaels
United States
Karen
¥13,693
¥15,062 total
includes taxes & fees
Aug 31 - Sep 1
St Michaels Inn

12. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
United States
Fabiana
¥15,622
¥17,808 total
includes taxes & fees
Sep 27 - Sep 28
DoubleTree by Hilton Hotel Annapolis

13. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
United States
Stephanie
¥21,636
¥23,800 total
includes taxes & fees
Sep 3 - Sep 4
Fairfield Inn & Suites by Marriott Easton

14. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
United States
Leslie
¥15,241
¥17,375 total
includes taxes & fees
Sep 27 - Sep 28
Country Inn & Suites by Radisson, Annapolis, MD

15. Best Western Annapolis

Best Western Annapolis
Annapolis
United States
George
¥12,825
¥14,620 total
includes taxes & fees
Sep 13 - Sep 14
Best Western Annapolis

16. Village Inn Annapolis MD

Village Inn Annapolis MD
Annapolis
United States
Stephen
¥13,287
¥15,148 total
includes taxes & fees
Aug 31 - Sep 1
Village Inn Annapolis MD

17. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
Stephanie
¥16,948
¥24,796 total
includes taxes & fees
Sep 29 - Sep 30
Historic Inns of Annapolis

18. Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG
Annapolis
United States
Frank
¥15,689
¥17,885 total
includes taxes & fees
Sep 27 - Sep 28
Holiday Inn Express & Suites Annapolis by IHG

19. Econo Lodge Easton Route 50

Econo Lodge Easton Route 50
Easton
United States
Nicole
¥12,966
¥14,263 total
includes taxes & fees
Sep 6 - Sep 7
Econo Lodge Easton Route 50

20. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
United States
Margaret
¥20,652
¥22,717 total
includes taxes & fees
Sep 28 - Sep 29
Best Western Plus Easton Inn & Suites
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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 boat docked at a pier during twilight with a city skyline in the background.
Photo by Patricia Knorr

Top Chester Hotel Reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

8/10 Good
"It is an older hotel, but clean. Breakfast was great! They have a good size pool, volleyball court, and basketball hoop. Rooms were very comfy and big. Great for families."
Heather 2-night trip
Posted less than an hour ago
Sonesta ES Suites Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Had a great stay. Check in was easy, room was clean, bed was comfortable and the cookies were great."
Amanda 1-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Great location and close to shops and restaurants. Very quiet/comfortable room with all the amenities and coffee available in the morning. Would definitely stay here again!"
Amy 3-night trip
Posted 2 hours ago
Historic Inns of Annapolis
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

8/10 Good
"Location was great, beds were comfortable and the room was clean."
Chris 1-night trip
Posted 13 hours ago
Best Western Kent Narrows Inn
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"Lovely room, clean, comfortable, well appointed & quiet. We’d be happy to stay longer in such a nice room! We asked for early check-in, & were told we’d be contacted when the room was ready, but there was no follow-up contact. Our morning shower had no hot water so we washed quickly! We knew there was ongoing work with the water supply but didn’t expect cold showers. When we reported the issue at the front desk, we were graciously offered breakfast at the on-site restaurant. So glad we accepted! Food (& service & view) were excellent. We didn’t consider the restaurant previously because there was no evidence of it aside from a sign on the door. A posted menu could help. It’s a long walk down a cold hallway and we totally would have not considered it as a breakfast option. Definitely recommend eating at the restaurant!"
Anita 1-night trip
Posted 23 hours ago
Annapolis Waterfront Hotel, Autograph Collection
St Michaels Inn

St Michaels Inn

8/10 Good
"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic work being done outside, which was a bit inconvenient, the hand rail was not tightened Staff was nice, especially Tamia at the front desk and Helena in the breakfast room. The rooms are spacious and the A/C works fine!"
CYNTHIA 3-night trip
Posted 2 days ago
St Michaels Inn
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Reception staff are very helpful, hassle free check in and out process.Good dining options within walking distance and very close to the marina and downtown area."
JOANA JENNIFER 2-night trip
Posted 2 days ago
Hilton Garden Inn Annapolis Downtown
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Great view of the water."
LINDA 1-night trip
Posted 3 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG
The Tidewater Inn

The Tidewater Inn

10/10 Excellent
"We had a lovely stay at Tidewater Inn centrally located in downtown Easton within walking distance of charming shops and delicious restaurants. Our room was spacious and light filled. The bathroom was small but adequate. We ate at the restaurant in the hotel (Hunters Tavern) and had a fabulous meal. Will definitely be back."
Lisa 1-night trip
Posted 7 days ago
The Tidewater Inn

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd Annapolis MD
¥12,825
¥14,620 total
Sep 13 - Sep 14
includes taxes & fees
7.8/10 Good! (1,002 reviews)
Best Western Annapolis
St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
¥13,693
¥15,062 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very Good! (1,012 reviews)
St Michaels Inn
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

124 Womack Dr Annapolis MD
¥15,622
¥17,809 total
Sep 10 - Sep 11
includes taxes & fees
Hampton Inn & Suites Annapolis
Holiday Inn Express & Suites Annapolis by IHG

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD
¥15,689
¥17,885 total
Sep 27 - Sep 28
includes taxes & fees
Holiday Inn Express & Suites Annapolis by IHG
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD
¥18,623
¥20,672 total
Sep 28 - Sep 29
includes taxes & fees
8/10 Very Good! (1,005 reviews)
Best Western Kent Narrows Inn
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

1020 Kent Narrows Rd Grasonville MD
¥19,691
¥21,857 total
Sep 28 - Sep 29
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
Holiday Inn Express Annapolis East-Kent Island by IHG

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.
What's the top vacation rental in Chester?
Cute, Cozy 2-bedroom house near Annapolis with water access: You might want to consider this vacation home rental near Chester, which offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the books in this rental home to help you unwind. 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?
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 Country Inn & Suites by Radisson, Annapolis, MD 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 Sandy Point Beach. You'll also find Queenstown Harbor Golf and Chesapeake Bay Bridge 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.

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