Chestertown, MD
Eagles Point Landing
About the 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.
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
For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Jul 17, 2026 | $1,525 | Available | 4 |
| Jul 18, 2026 | $1,525 | Available | 4 |
| Jul 19, 2026 | $1,525 | Available | 4 |
| Jul 20, 2026 | $1,525 | Available | 4 |
| Jul 21, 2026 | $1,525 | Available | 4 |
| Jul 22, 2026 | $1,525 | Available | 4 |
| Jul 23, 2026 | $1,525 | Available | 4 |
| Jul 24, 2026 | $1,525 | Available | 4 |
| Jul 25, 2026 | $1,525 | Available | 4 |
| Jul 26, 2026 | $1,525 | Available | 4 |
| Jul 27, 2026 | $1,525 | Available | 4 |
| Jul 28, 2026 | $1,525 | Available | 4 |
| Jul 29, 2026 | $1,525 | Available | 4 |
| Jul 30, 2026 | $1,525 | Available | 4 |
| Jul 31, 2026 | $1,525 | Available | 4 |
| Aug 1, 2026 | $1,525 | Available | 4 |
| Aug 2, 2026 | $1,525 | Available | 4 |
| Aug 3, 2026 | $1,525 | Available | 4 |
| Aug 4, 2026 | $1,525 | Available | 4 |
| Aug 5, 2026 | $1,525 | Available | 4 |
| Aug 6, 2026 | $1,525 | Available | 4 |
| Aug 7, 2026 | $1,525 | Available | 4 |
| Aug 8, 2026 | $1,525 | Available | 4 |
| Aug 9, 2026 | $1,525 | Available | 4 |
| Aug 10, 2026 | $1,525 | Available | 4 |
| Aug 11, 2026 | $1,525 | Available | 4 |
| Aug 12, 2026 | $1,525 | Available | 4 |
| Aug 13, 2026 | $1,525 | Available | 4 |
| Aug 14, 2026 | $1,525 | Available | 4 |
| Aug 15, 2026 | $1,525 | Available | 4 |
| Aug 16, 2026 | $1,525 | Available | 4 |
| Aug 17, 2026 | $1,525 | Available | 4 |
| Aug 18, 2026 | $1,525 | Available | 4 |
| Aug 19, 2026 | $1,525 | Available | 4 |
| Aug 20, 2026 | $1,525 | Available | 4 |
| Aug 21, 2026 | $1,525 | Available | 4 |
| Aug 22, 2026 | $1,525 | Available | 4 |
| Aug 23, 2026 | $1,525 | Available | 4 |
| Aug 24, 2026 | $1,525 | Available | 4 |
| Aug 25, 2026 | $1,525 | Available | 4 |
| Aug 26, 2026 | $1,525 | Available | 4 |
| Aug 27, 2026 | $1,525 | Available | 4 |
| Aug 28, 2026 | $1,525 | Available | 4 |
| Aug 29, 2026 | $1,525 | Available | 4 |
| Aug 30, 2026 | $1,525 | Available | 4 |
| Aug 31, 2026 | $1,525 | Available | 4 |
| Sep 1, 2026 | $1,525 | Available | 4 |
| Sep 2, 2026 | $1,525 | Available | 4 |
| Sep 3, 2026 | $1,525 | Available | 4 |
| Sep 4, 2026 | $1,525 | Available | 4 |
| Sep 5, 2026 | $1,525 | Available | 4 |
| Sep 6, 2026 | $1,525 | Available | 4 |
| Sep 7, 2026 | $1,525 | Available | 4 |
| Sep 8, 2026 | $1,525 | Available | 4 |
| Sep 9, 2026 | $1,525 | Available | 4 |
| Sep 10, 2026 | $1,525 | Available | 4 |
| Sep 11, 2026 | $1,550 | Available | 4 |
| Sep 12, 2026 | $1,550 | Available | 4 |
| Sep 13, 2026 | $1,550 | Available | 4 |
| Sep 14, 2026 | $1,550 | Available | 4 |
| Sep 15, 2026 | $1,100 | Available | 4 |
| Sep 16, 2026 | $1,100 | Available | 4 |
| Sep 17, 2026 | $1,100 | Available | 4 |
| Sep 18, 2026 | $1,100 | Available | 4 |
| Sep 19, 2026 | $1,100 | Available | 4 |
| Sep 20, 2026 | $1,100 | Available | 4 |
| Sep 21, 2026 | $1,100 | Available | 4 |
| Sep 22, 2026 | $1,100 | Available | 4 |
| Sep 23, 2026 | $1,100 | Available | 4 |
| Sep 24, 2026 | $1,100 | Available | 4 |
| Sep 25, 2026 | $1,100 | Available | 4 |
| Sep 26, 2026 | $1,100 | Available | 4 |
| Sep 27, 2026 | $1,100 | Available | 4 |
| Sep 28, 2026 | $1,100 | Available | 4 |
| Sep 29, 2026 | $1,100 | Available | 4 |
| Sep 30, 2026 | $1,100 | Available | 4 |
| Oct 1, 2026 | $1,100 | Available | 4 |
| Oct 2, 2026 | $1,100 | Available | 4 |
| Oct 3, 2026 | $1,100 | Available | 4 |
| Oct 4, 2026 | $1,100 | Available | 4 |
| Oct 5, 2026 | $1,100 | Available | 4 |
| Oct 6, 2026 | $1,100 | Available | 4 |
| Oct 7, 2026 | $1,100 | Available | 4 |
| Oct 8, 2026 | $1,100 | Available | 4 |
| Oct 9, 2026 | $1,100 | Available | 4 |
| Oct 10, 2026 | $1,100 | Available | 4 |
| Oct 11, 2026 | $1,100 | Available | 4 |
| Oct 12, 2026 | $1,100 | Available | 4 |
| Oct 13, 2026 | $1,100 | Available | 4 |
| Oct 14, 2026 | $1,100 | Available | 4 |
| Oct 15, 2026 | $1,100 | Available | 4 |
Amenities
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Where you'll be
Chestertown, MD, 21620, United States of America
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
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
Our promise to you
Lower prices, every time
Direct line, real care
Not just a transaction
You'll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We're building a relationship, not closing a booking.