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
Property grounds
First Floor Studio Apartment in Historic Chestertown

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.
The price is AED 364
AED 583 total
includes taxes & fees
15 Dec - 16 Dec
First Floor Studio Apartment in Historic Chestertown
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
Property grounds
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Queen Anne
10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
United States
Catherine M.
The price is AED 694
AED 1,316 total
includes taxes & fees
22 Dec - 23 Dec
Adorable two-bedroom retreat close to Easton, Denton, Centreville
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit
Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is AED 724
AED 1,612 total
includes taxes & fees
15 Dec - 16 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is AED 1,187
AED 2,223 total
includes taxes & fees
15 Dec - 16 Dec
5-bedroom vacation home 5 minutes from historic Charlestown
Beach
Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is AED 643
AED 1,144 total
includes taxes & fees
14 Dec - 15 Dec
Waterfront Retreat with Private Dock and Beach
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, (933)
"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, (601)
"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
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.