Find Golf Hotels in Chestertown, MD

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Check availability on Chestertown Golf Hotels

Our top choices for Chestertown hotels with a golf course

Golf
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is AED 364
AED 416 total
includes taxes & fees
15 Dec - 16 Dec
The Lodge at Great Oak Landing
Reception
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (861)
"The breakfast was was very good with lots of options depending on your dietary needs."
United States
Terry
The price is AED 341
AED 378 total
includes taxes & fees
6 Jan - 7 January 2026
Hampton Inn Middletown
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (932)
"It was very comfortable and clean"
United States
Maria
The price is AED 320
AED 355 total
includes taxes & fees
3 Jan - 4 January 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (337)
"The breakfast menu was okay but not great. The overall hotel was very nice and the staff were friendly."
United States
Gregory
The price is AED 256
AED 286 total
includes taxes & fees
10 Jan - 11 January 2026
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (600)
"very pet friendly!!"
United States
larry
The price is AED 332
AED 372 total
includes taxes & fees
10 Jan - 11 January 2026
Hampton Inn & Suites Baltimore/Aberdeen
Bar (on property)
Travelodge by Wyndham Aberdeen

Travelodge by Wyndham Aberdeen

Travelodge by Wyndham Aberdeen
2.0 star property
Aberdeen
6.4 out of 10, (535)
"The Great place to stay "
United States
Hector
The price is AED 209
AED 234 total
includes taxes & fees
28 Dec - 29 Dec
Travelodge by Wyndham Aberdeen
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is AED 527
AED 716 total
includes taxes & fees
14 Dec - 15 Dec
Kent Island Resort
Exterior
Holiday Inn Belcamp - Aberdeen Area by IHG

Holiday Inn Belcamp - Aberdeen Area by IHG

Holiday Inn Belcamp - Aberdeen Area by IHG
3.0 star property
Belcamp
8.4 out of 10, Very Good, (738)
"the room was spotless and the breakfast was very nice."
United States
Carl
The price is AED 261
AED 292 total
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Belcamp - Aberdeen Area by IHG
Lobby
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1004)
"The room was very nice as well as the staff. The guy at the desk let us check in early which was super helpful for us! Would definitely recommend and come back to again! "
United States
Sara
The price is AED 305
AED 342 total
includes taxes & fees
4 Jan - 5 January 2026
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Vending machine
Red Roof Inn Edgewood

Red Roof Inn Edgewood

Red Roof Inn Edgewood
2.0 star property
Edgewood
7.2 out of 10, Good, (848)
"Room was runned down,staff was excellent,amenities ok,"
United States
Alane
The price is AED 244
AED 274 total
includes taxes & fees
1 Jan - 2 January 2026
Red Roof Inn Edgewood
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 Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful area! Loved the room! We took a taxi from the airport, it was nice to not have to worry about parking."
Amy 3-night trip
Posted 2 days ago
Historic Inns of Annapolis

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Frequently asked questions

Are you looking for a golf hotel in Chestertown?
From golf lessons to driving ranges to evening entertainment, Expedia is the place to book your golfing weekend. Families can enjoy sporting events and boating. Also, check out the historical sites and art galleries in Chestertown.
What is the best golf hotel in Chestertown?
The Lodge at Great Oak Landing is a top beach hotel boasting a 9-hole golf course. The hotel also features 3 bars, a 24-hour fitness center, a restaurant, and free WiFi.
How many golf hotels are there in Chestertown?
Expedia has 1 accommodation option in Chestertown classified as a golf hotel.
What should I see and do in Chestertown while on a golf vacation?
When you're ready to take a break from the links, you'll discover that Chestertown has a lot to offer. Explore the local sights and attractions with a stop at Historical Society of Kent County Maryland, Chestertown Historic District, and Crumpton Auction. Also, don't miss Northern Chesapeake Bay, Chesapeake Bay, and Rolphs Wharf Marina.
What is a golf hotel in Chestertown like?
Golf hotels in Chestertown offer lodging and convenient access to a golf course. On Expedia, you will be able to find a wide selection of golf hotels which have either a 9+ hole golf course, or that are located adjacent to an 18+ hole golf course. Golf hotels provide a selection of services and amenities such as golf equipment, lessons, and shuttles.