Chestertown, MD

Eagles Point Landing

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8 guests
4 bedrooms
4 bathrooms
1000 sqft

Eagles Point Landing

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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.

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.

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

Amenities

  • Bathroom 1
      Shower
  • Bathroom 2
      Hair dryer
  • Bathroom 3
      Bathtub
  • Living room
      Fire place
      TV
      Air conditioning
      Heating
      Ceiling fan
  • Common area
      Wifi
      First aid kit
      Fire extinguisher
  • Pool
      Pool outdoor
  • Kitchen
      Kitchen
      Dishwasher
      Microwave
      Oven
      Coffee maker
      Fridge
  • Laundry room
      Washer
      Dryer
      Iron
  • Office
      Dedicated workspace
  • Exterior
      Tennis court
      Pet relief area
      Kayaks
  • Garage
      Free parking
  • Patio
      Patio
      BBQ Utensils
  • Garden
      Garden
  • Game room
      Game Room
  • Gym
      Gym
  • Boat dock
      Boat dock
  • Bedroom 1
      Hangers
  • Bedroom 2
      Crib
  • Bedroom 3
      Bed linens

Where you'll sleep

Bedroom 1
  • 1 queen bed
  • 1 twin bed
 Bedroom 2
  • 1 queen bed
 Bedroom 3
  • 1 queen bed
 Bedroom 4
  • 1 twin bed

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

House rules

This home follows a strict maximum occupancy rule. Please make sure that the total number of guests accompanying you (including both children and adults) doesn't exceed the indicated maximum occupancy above to avoid cancellation of your stay and additional fees.

Cancellation policy

This property follows Tidewater Vacations’s standard cancellation policy.

Cancellation policy

1. Refundable Bookings
Cancellation Deadlines
• For stays under 15 nights, you may cancel or reschedule up to 14 days before check-in for a full refund. For stays 15 nights or longer, the cancellation window is 60 days.
• For some homes, a 30-day deadline applies — this will be clearly shown before you book.
• Cancellations must be submitted before 4 PM EST on the deadline day to qualify.
After the deadline - Fair-Refund policy
• If you cancel after the deadline:
• Tidewater Vacations will relist your dates and automatically refund you for any nights that rebook.
• The refund per night will be the lower of the original price or rebooking rate.
• Nights that do not rebook are non-refundable.
2. Non-refundable Bookings
• If you selected a Non-Refundable rate at checkout, the booking cannot be changed or canceled, and no refund will be issued.
3. Half-Now-Half-Later Bookings
• The first half of your payment is non-refundable.
• The second half may be refunded according to the standard cancellation policy.
4. Date Changes & Rebooking
• Once a stay is canceled, you can't rebook the same dates yourself.
• If you need help choosing new dates, our Concierge team is happy to assist.
5. Transfers to Another Guest
• You may transfer your booking to someone else at no charge.
• Just contact the Concierge with the new guest's name and email.
• The new guest must accept the transfer for it to take effect.
6. Policy Match Guarantee
• If a better price is available for the same property on Airbnb or the owner's site, contact the Concierge — Tidewater Vacations will match it.
Final Note
By completing your booking, you acknowledge and agree to Tidewater Vacations's cancellation policy.