Curated Golf Guide

Best Golf Courses in Chestertown

Discover the top-rated golf destinations in Chestertown. We've analyzed reviews and data from 3 local courses to help you find the perfect round.

2.3 Avg Rating
4,100 Avg Yards

Golf in Chestertown — 2026 Guide

Chestertown is home to 3 golf courses with an average player rating of 2.3 out of 5. Courses here average 4,100 yards in length, with the longest stretching 6,355 yards.

Browse our ranked list below to compare courses by rating, yardage, and hole count. Each listing links to detailed scorecards, photos, and player reviews to help you plan your next round.

Editor's Picks for Chestertown

⛳ The Longest Drive

Chester River Yacht & Country Club

6,355 yd from the back tees

A true test of distance. Bring your driver and get ready to cover some serious ground.

👥 Fan Favorite

Chester River Yacht & Country Club

1 reviews

The most reviewed course in town. A popular choice among local players and visitors alike.

All Top Courses in Chestertown

#1

Green Mansions Golf Club

Chestertown, New York

4.0 Rating
9 Holes
2,701 yd Length

Not far from Chestertown, Green Mansions Golf Club offers terrific views and challenging play for golfers at every skill level. Well-groomed fairwa...

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#2

Chester River Yacht & Country Club

Chestertown, Maryland

3.0 Rating
18 Holes
6,355 yd Length

Not far from Chestertown, Chester River Yacht & Country Club offers terrific views and challenging play for golfers at every skill level. Well-groo...

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#3

Great Oak Landing Marina

Chestertown, Maryland

9 Holes
3,244 yd Length

Not far from Chestertown, Great Oak Landing Marina offers terrific views and challenging play for golfers at every skill level. Well-groomed fairwa...

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📍 Expand Your Search

Looking for more options? Find courses within driving distance of Chestertown.

Find Courses Within 25 Miles