Find Golf Resorts & Hotels in Chestertown, MD from $69

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Top Chestertown Golf Hotels

Golf
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
$113 nightly
The price is $126
Dec 10 - Dec 11
Total with taxes and fees
The Lodge at Great Oak Landing
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 10 - Dec 11
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (599)
"very pet friendly!!"
United States
larry
$90 nightly
The price is $101
Dec 19 - Dec 20
Total with taxes and fees
Hampton Inn & Suites Baltimore/Aberdeen
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
8.8 out of 10, Excellent, (860)
"The breakfast was was very good with lots of options depending on your dietary needs."
United States
Terry
$93 nightly
The price is $103
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hampton Inn Middletown
Aerial view
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
$163 nightly
The price is $177
Dec 11 - Dec 12
Total with taxes and fees
Kent Island Resort
Terrace/patio
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
$80 nightly
The price is $90
Dec 19 - Dec 20
Total with taxes and fees
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Exterior
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, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
$87 nightly
The price is $97
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby
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, (1001)
"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
$84 nightly
The price is $94
Dec 30 - Dec 31
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Desk, free WiFi, bed sheets, alarm clocks
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 star property
Edgewood
7.4 out of 10, Good, (1004)
"Good stay "
United States
D
$62 nightly
The price is $69
Jan 1 - Jan 2, 2026
Total with taxes and fees
Quality Inn & Suites Bel Air I-95 Exit 77A
Free daily buffet breakfast
Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
Nottingham
8.6 out of 10, Excellent, (1005)
"Great place to stay"
United States
brian
$101 nightly
The price is $117
Dec 14 - Dec 15
Total with taxes and fees
Fairfield Inn & Suites by Marriott White Marsh
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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Clean room, great location, very friendly and helpful staff"
Beverly 1-night trip
Posted 13 hours ago
Best Western Plus Hotel & Conference Center

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 Rolphs Wharf Marina. Also, don't miss Crumpton Auction, Northern Chesapeake Bay, and Chesapeake Bay.
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.

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