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Eagles Point Landing-Private Pool, Dock, Pickleball

Photo gallery for Eagles Point Landing-Private Pool, Dock, Pickleball

Pool
Bedroom1 Desk
Living Room
Chefs Kitchen
Foyer

Reviews

10 out of 10
Exceptional

Highlights

  • Bring your furry friends
    Top-rated for creating memorable stays with your pets.
  • Pickleball on-site
    A rare find — enjoy pickleball without leaving the property.
4 bedrooms4 bathroomsSleeps 8

Popular amenities

  • Private pool
  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View in a map
Chestertown, MD
  • Place, Washington College
    ‪7 min drive‬
  • Place, Chestertown Dog Park
    ‪7 min drive‬
  • Place, Chestertown Historic District
    ‪8 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪121 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Single Beds

4 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Balcony
Separate dining area
Outdoor play area
Garden
Dining area

About this property

Eagles Point Landing-Private Pool, Dock, Pickleball

350 Acres, Private Pool, Dock, Pickleball and more
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.
A signed Tidewater Vacation Rental Agreement must be signed within 72 hours of booking.

You are staying in someone’s home, so please treat it with the same care and respect you’d expect for your own place.

Use of property, pool, dock and any other amenities is at individuals own risk. Owner and agent shall not be held responsible for any accidents or injury that occurs on the property during stay

Due to the rural nature of the area, this property may experience slow internet speeds, limited access to email, web browsing and streaming services

Due to local zoning ordinances weddings and special events are not permitted at this property. No parties or events are permitted on this property during stay

Due to the local `Noise Ordinance` no parties are allowed at our properties and quite hours are between 10:00 PM & 7:00 AM

This property does not allow group rentals to guests under the age of 25. Any group rental made by an individual under the age of 25 will not be honored

Every effort has been made to ensure the accuracy of the images, descriptions, and amenities. Although they are deemed reliable, they cannot be guaranteed

No refunds will be given due to amenity discrepancies or area event closures/cancellations

Check-in / Check-out dates and times are strictly followed

All Trash is to be bagged and placed in outside trash receptacles
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 24
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
Fees Apply
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Smoking

Smoking is not permitted
A signed Tidewater Vacation Rental Agreement must be signed within 72 hours of booking.

Important information

You need to know

Property # 5111298vb
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is no smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Chestertown

Located in Chestertown, this holiday home is in the city centre and on the waterfront. The area's natural beauty can be seen at Urieville Lake Fish Management Area and Urieville Park, while Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater are cultural highlights. Larrabee Arts Center and Crumpton Auction are also worth visiting. Kayaking and water tubing offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and hiking/biking trails nearby.
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Map
Chestertown, MD

What's nearby

  • Washington College - 7 min drive - 8.0 km
  • Chestertown Dog Park - 7 min drive - 8.0 km
  • Chestertown Historic District - 8 min drive - 10.1 km
  • Historical Society of Kent County Maryland - 8 min drive - 10.1 km
  • River Arts Chestertown - 8 min drive - 10.4 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 113 min drive

Restaurants

  • ‪Milano's Pizzeria - ‬12 min drive
  • ‪McDonald's - ‬9 min drive
  • ‪Dunkin - ‬8 min drive
  • ‪Royal Farms - ‬12 min drive
  • ‪Cafe Sado - ‬9 min drive

Frequently asked questions

Is Eagles Point Landing-Private Pool, Dock, Pickleball pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Eagles Point Landing-Private Pool, Dock, Pickleball?

As of 24 Aug 2026, prices found for a 1-night stay for 2 adults at Eagles Point Landing-Private Pool, Dock, Pickleball on 26 Jan 2027 start from £3,735, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Eagles Point Landing-Private Pool, Dock, Pickleball?

On-site parking is available at the property.

What time is check-in at Eagles Point Landing-Private Pool, Dock, Pickleball?

Check-in begins at 4:00 PM.

What time is check-out at Eagles Point Landing-Private Pool, Dock, Pickleball?

Checkout is at 10:00 AM.

Where is Eagles Point Landing-Private Pool, Dock, Pickleball located?

Located in the heart of Chestertown, this holiday home is within 6 miles (10 km) of Urieville Lake Fish Management Area, Urieville Park and Chestertown Dog Park. Chase Island and Washington College are also within 6 miles (10 km).

About the host

Hosted by Tidewater Vacation Rentals LLC

Host profile image

Languages:

English
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