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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, (1,002 reviews)
"A wonderful stay! Already planning a trip for next year!"
United States
Michelle
The price is CA $134
CA $149 total
includes taxes & fees
Dec 6 - Dec 7
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, (857 reviews)
"Great place to stay"
United States
Michael
The price is CA $189
CA $210 total
includes taxes & fees
Nov 15 - Nov 16
Hyatt Place Kent Narrows & Marina

3. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,002 reviews)
"Everything was fantastic"
United States
Gamil
The price is CA $169
CA $188 total
includes taxes & fees
Nov 18 - Nov 19
Hilton Garden Inn Kent Island Marina

4. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,003 reviews)
"Nice location & stay"
United States
Holly
The price is CA $127
CA $141 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Kent Narrows Inn

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, (512 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is CA $256
CA $320 total
includes taxes & fees
Dec 9 - Dec 10
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, (1,001 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
The price is CA $117
CA $130 total
includes taxes & fees
Nov 29 - Nov 30
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 CA $173
CA $239 total
includes taxes & fees
Nov 30 - Dec 1
Kent Island Resort

8. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,064 reviews)
"Great location, excellent stay"
United States
Christiaan
The price is CA $101
CA $163 total
includes taxes & fees
Nov 17 - Nov 18
Historic Inns of Annapolis

9. 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 CA $127
CA $366 total
includes taxes & fees
Nov 12 - Nov 13
Cass-N-Reel Luxury Houseboat

10. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,273 reviews)
"Excellent staff & service!"
United States
Michele
The price is CA $126
CA $144 total
includes taxes & fees
Nov 10 - Nov 11
DoubleTree by Hilton Hotel Annapolis

11. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.0 out of 10, Very good, (1,005 reviews)
"Staff was very pleasant. Room was clean and a very nice Breakfast included."
United States
Dean
The price is CA $105
CA $115 total
includes taxes & fees
Dec 8 - Dec 9
St Michaels Inn

12. Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (534 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 CA $117
CA $134 total
includes taxes & fees
Nov 9 - Nov 10
Village Inn Annapolis MD

13. Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,008 reviews)
"Great location, friendly staff."
United States
Joel
The price is CA $138
CA $157 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Annapolis Downtown

14. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,010 reviews)
"Brunch was the best we had the whole trip! Excellent food and wonderful staff."
United States
REBECCA
The price is CA $184
CA $210 total
includes taxes & fees
Nov 29 - Nov 30
Graduate by Hilton Annapolis

15. 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)
"Great breakfast and hot tub"
United States
Marc
The price is CA $134
CA $153 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Express & Suites Annapolis by IHG

16. 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 CA $119
CA $392 total
includes taxes & fees
Nov 9 - Nov 10
Charming Coastal/Country Home w/3 Acres & Sauna!

17. 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 CA $198
CA $220 total
includes taxes & fees
Nov 16 - Nov 17
Inn at Huntingfield Creek

18. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,010 reviews)
"Great location"
United States
Jose
The price is CA $146
CA $166 total
includes taxes & fees
Dec 6 - Dec 7
Crowne Plaza Annapolis by IHG

19. The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,004 reviews)
"This is a fabulous resort! Very clean, great location and the staff is great!"
United States
Bobbi
The price is CA $239
CA $272 total
includes taxes & fees
Nov 15 - Nov 16
The Westin Annapolis

20. Queenstown Harbor Golf Resort

Queenstown Harbor Golf Resort
2.5 star property
Queenstown
The price is CA $469
CA $534 total
includes taxes & fees
Nov 16 - Nov 17
Queenstown Harbor Golf Resort
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.

Learn more about Chester

Chester awaits: its island views, sunny weather, golf, and more!

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

Top reviews in Chester

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.

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