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

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Recommended hotels in Chester

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, (1,001 reviews)
"Staff was very friendly."
United States
Michelle
The price is AED 349
AED 387 total
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG

2. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (861 reviews)
"Great place to stay"
United States
Michael
The price is AED 493
AED 547 total
includes taxes & fees
15 Nov - 16 Nov
Hyatt Place Kent Narrows & Marina

3. 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)
"Nice location & stay"
United States
Holly
The price is AED 330
AED 366 total
includes taxes & fees
19 Nov - 20 Nov
Best Western Kent Narrows Inn

4. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,001 reviews)
"Everything was fantastic"
United States
Gamil
The price is AED 449
AED 498 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Kent Island Marina

5. 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, (514 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is AED 665
AED 832 total
includes taxes & fees
9 Dec - 10 Dec
The Inn at Chesapeake Bay Beach Club

6. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (1,004 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
The price is AED 303
AED 336 total
includes taxes & fees
13 Dec - 14 Dec
Quality Inn Grasonville near Kent Island

7. Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (190 reviews)
"Just a wonderful place, we had an amazing stay!"
United States
Bethany
The price is AED 449
AED 620 total
includes taxes & fees
1 Dec - 2 Dec
Kent Island Resort

8. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,066 reviews)
"Great location, excellent stay"
United States
Christiaan
The price is AED 262
AED 424 total
includes taxes & fees
23 Nov - 24 Nov
Historic Inns of Annapolis

9. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.0 out of 10, Very good, (1,002 reviews)
"Convenient to St Michael’s and inexpensive."
United States
John
The price is AED 289
AED 318 total
includes taxes & fees
1 Dec - 2 Dec
St Michaels Inn

10. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,011 reviews)
"Great location, friendly staff."
United States
Joel
The price is AED 358
AED 409 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Annapolis Downtown

11. Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (535 reviews)
"very clean room. All the basic items you need from a budget motel. I admit on the outside the motel looks a bit rough, but inside the rooms where it really matters, it was clean, well organized, and comfortable. I would stay here again, if I was looking for a cheap accommodation in the Annapolis area. Despite being right next to a busy state highway, it was very quiet and conveniently located to a couple of local restaurants and a convenience store."
United States
Keith
The price is AED 305
AED 348 total
includes taxes & fees
15 Nov - 16 Nov
Village Inn Annapolis MD

12. 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, (1,000 reviews)
"Great breakfast and hot tub"
United States
Marc
The price is AED 349
AED 398 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express & Suites Annapolis by IHG

13. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,278 reviews)
"i enjoyed how close the place was to many local shops and resturants."
United States
michel demanche
The price is AED 328
AED 374 total
includes taxes & fees
22 Nov - 23 Nov
DoubleTree by Hilton Hotel Annapolis

14. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,001 reviews)
"Great location"
United States
Jose
The price is AED 378
AED 431 total
includes taxes & fees
13 Dec - 14 Dec
Crowne Plaza Annapolis by IHG

15. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.2 out of 10, Wonderful, (1,014 reviews)
"Brunch was the best we had the whole trip! Excellent food and wonderful staff."
United States
REBECCA
The price is AED 479
AED 546 total
includes taxes & fees
29 Nov - 30 Nov
Graduate by Hilton Annapolis

16. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (54 reviews)
"Love This rental. One of our favorites. Small but everything needed. And the view is absolutely wonderful."
United States
Yamilet
The price is AED 331
AED 943 total
includes taxes & fees
15 Nov - 16 Nov
Cass-N-Reel Luxury Houseboat

17. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,000 reviews)
"Excellent location, Very nice Hotel"
United States
Loraine
The price is AED 584
AED 666 total
includes taxes & fees
15 Nov - 16 Nov
The Westin Annapolis

18. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
The price is AED 515
AED 571 total
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek

19. Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (250 reviews)
"Nice hotel"
United States
Imola
The price is AED 437
AED 498 total
includes taxes & fees
17 Nov - 18 Nov
Fairfield Inn & Suites By Marriott Annapolis

20. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (50 reviews)
"Great stay"
United States
Michael V.
The price is AED 441
AED 1,206 total
includes taxes & fees
23 Nov - 24 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
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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Top Chester Hotel Reviews

Frequently asked questions

What can I look forward to during my Chester aparthotel stay?
You're likely to stay centrally in Chester with an aparthotel or serviced apartment. You can also come to Chester for its waterfront and seafood restaurants.
What is the best aparthotel for my stay in Chester?
Located 20.5 mi (33 km) from Chester, Town View King Apartment with Private Beach - Walk to shops and restaurants is a favorite aparthotel and the apartment offers a kitchen and free WiFi. Sandaway Suites & Beach - Full Kitchen & Private Beach Access - Location in Town is another top aparthotel you might want to consider in the larger area.
How many aparthotels will I find in Chester?
Bookable on Expedia, you'll find 9 lodging options in Chester. Though not many aparthotels, we can help you find places to stay that are similar such as a condo or apartment.
What should I see and do in Chester?
Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Northern Chesapeake Bay. Matapeake State Park and Eastern Neck National Wildlife Refuge are a couple of places you'll find in the larger area.
What is an aparthotel?
An aparthotel is part hotel and part apartment, providing the amenities you expect from a traditional hotel, and more space and privacy found in an apartment. These accommodations are often situated in the center of Chester, where you can meet the locals. Enjoy cooking in a fully-equipped kitchen and having extra space to spread out while you're in town.