Chestertown, MD

Eagles Point Landing

Copied to clipboard
Click to copy
8 guests
4 bedrooms
4 bathrooms
1000 sqft

Experience unparalleled privacy and endless natural beauty at Eagles Point!

8 guests
4 bedrooms
4 bathrooms
1000 sqft

  • Flexible check-in & out

    Check-in after 4:00 PM • Check-out before 10:00 AM

  • Easy cancellation


About this property

Experience unparalleled privacy and endless natural beauty at Eagles Point! This stunning 350-acre waterfront estate on the Chester River in historic Chestertown, Maryland is a rare private retreat that combines expansive open landscapes, premium recreational amenities, and easy access to the charm of Maryland's Eastern Shore. Eagles Point spans 350 acres of pristine waterfront land, featuring open fields, wooded trails, abundant wildlife, and direct access to the scenic Chester River. Wake up to beautiful water views and enjoy complete seclusion while still being just minutes from downtown Chestertown's historic district. This is the perfect location for family vacations, group retreats, romantic getaways, or peaceful nature escapes.

Experience unparalleled privacy and endless natural beauty at Eagles Point! This stunning 350-acre waterfront estate on the Chester River in historic Chestertown, Maryland is a rare private retreat that combines expansive open landscapes, premium recreational amenities, and easy access to the charm of Maryland's Eastern Shore. Eagles Point spans 350 acres of pristine waterfront land, featuring open fields, wooded trails, abundant wildlife, and direct access to the scenic Chester River. Wake up to beautiful water views and enjoy complete seclusion while still being just minutes from downtown Chestertown's historic district. This is the perfect location for family vacations, group retreats, romantic getaways, or peaceful nature escapes.

Availability & Pricing

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Mar 7, 2026$880Available4
Mar 8, 2026$880Available4
Mar 9, 2026$880Available4
Mar 10, 2026$880Available4
Mar 11, 2026$880Available4
Mar 12, 2026$880Available4
Mar 13, 2026$880Available4
Mar 14, 2026$880Available4
Mar 15, 2026$880Available4
Mar 16, 2026$880Available4
Mar 17, 2026$880Available4
Mar 18, 2026$880Available4
Mar 19, 2026$880Available4
Mar 20, 2026$880Available4
Mar 21, 2026$880Available4
Mar 22, 2026$880Available4
Mar 23, 2026$880Available4
Mar 24, 2026$880Available4
Mar 25, 2026$880Available4
Mar 26, 2026$880Available4
Mar 27, 2026$880Available4
Mar 28, 2026$880Available4
Mar 29, 2026$880Available4
Mar 30, 2026$880Available4
Mar 31, 2026$880Available4
Apr 1, 2026$880Available4
Apr 2, 2026$880Available4
Apr 3, 2026$880Available4
Apr 4, 2026$880Available4
Apr 5, 2026$880Available4
Apr 6, 2026$880Available4
Apr 7, 2026$880Available4
Apr 8, 2026$880Available4
Apr 9, 2026$880Available4
Apr 10, 2026$880Available4
Apr 11, 2026$880Available4
Apr 12, 2026$880Available4
Apr 13, 2026$880Available4
Apr 14, 2026$880Available4
Apr 15, 2026$880Available4
Apr 16, 2026$880Available4
Apr 17, 2026$880Available4
Apr 18, 2026$880Available4
Apr 19, 2026$880Available4
Apr 20, 2026$880Available4
Apr 21, 2026$880Available4
Apr 22, 2026$880Available4
Apr 23, 2026$880Available4
Apr 24, 2026$880Available4
Apr 25, 2026$880Available4
Apr 26, 2026$880Available4
Apr 27, 2026$880Available4
Apr 28, 2026$880Available4
Apr 29, 2026$880Available4
Apr 30, 2026$880Available4
May 1, 2026$880Available4
May 2, 2026$880Available4
May 3, 2026$880Available4
May 4, 2026$880Available4
May 5, 2026$880Available4
May 6, 2026$880Available4
May 7, 2026$880Available4
May 8, 2026$880Available4
May 9, 2026$880Available4
May 10, 2026$880Available4
May 11, 2026$880Available4
May 12, 2026$880Available4
May 13, 2026$880Available4
May 14, 2026$880Available4
May 15, 2026$880Available4
May 16, 2026$880Available4
May 17, 2026$880Available4
May 18, 2026$880Available4
May 19, 2026$880Available4
May 20, 2026$880Available4
May 21, 2026$880Available4
May 22, 2026$880Available4
May 23, 2026$880Available4
May 24, 2026$880Available4
May 25, 2026$880Available4
May 26, 2026$880Available4
May 27, 2026$880Available4
May 28, 2026$880Available4
May 29, 2026$880Available4
May 30, 2026$880Available4
May 31, 2026$880Available4
Jun 1, 2026$880Available4
Jun 2, 2026$880Available4
Jun 3, 2026$880Available4
Jun 4, 2026$880Available4
Jun 5, 2026$880Available4

Amenities

Shower
Hair dryer
Bathtub
Fire place
TV
Air conditioning
Heating
Ceiling fan
Wifi

Where you'll sleep



Explore Chestertown, MD

Experience the refined tranquility of the riverside community in Chestertown. A short drive leads to the vibrant town center, where you can explore the preserved architecture of Chestertown Maryland, browse the Chestertown Farmers Market, or stroll along the water at Wilmer Park and Chestertown Marina LLC. Discover local flavors with a visit to Lockbriar Farms for fresh ice cream or stock up on gourmet essentials at ACME Markets

Things to know

Here are some things which you should know before booking Eagles Point Landing

House rules

Check-in after 4:00 PM
Check-out before 10:00 AM
8 guests maximum
Pets not allowed
No smoking - fees will apply
Events not permitted
Commercial photography requires approval

Cancellation policy

This property follows Tidewater Vacations’s standard cancellation policy.