See all properties
Entire home

Eagles Point Landing

Choose dates to view prices

Photo gallery for Eagles Point Landing

Relaxing Pool Days
And the View
Upper Deck View
Outside Upper Deck Area
Open Kitchen

Reviews

10 out of 10
Exceptional
4 bedrooms4 bathroomsSleeps 8

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
$1,741
avg per night

Explore the area

View in a map
Chestertown, MD
  • Place, Chestertown Dog Park
    ‪6 min drive‬
  • Place, Rolling Road Park
    ‪6 min drive‬
  • Place, Washington College
    ‪7 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪102 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 Twin 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
Price is $1,741 avg per night

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

View from deck of brick patio, fire pit area, & pier w/ separate floating dock.
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Chestertown
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
10.0 out of 10, Exceptional, 108 reviews
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

About the neighborhood

Chestertown

Located in Chestertown, this vacation home is in the city center 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. Be sure to check out the area's animals with activities such as game walks and birdwatching.
View more Vacation Homes in ChestertownOpens in a new window

What's nearby

  • Chestertown Dog Park - 6 min drive - 7.3 km
  • Rolling Road Park - 6 min drive - 7.3 km
  • Washington College - 7 min drive - 8.0 km
  • Historical Society of Kent County Maryland - 8 min drive - 10.1 km
  • Garfield Center for the Arts at the Prince Theater - 8 min drive - 10.1 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
  • ‪Procolino's - ‬8 min drive

About this property

Eagles Point Landing

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.

Amenities

Pool
Kitchen
Washer
Dryer
Pet friendly
Free WiFi

House Rules

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

Children

Children allowed: ages 0-17
default

Events

No events allowed
default

Pets

Pets allowed
Fees Apply
default

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

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
Onsite parties or group events are strictly prohibited
Host has indicated there are no carbon monoxide detectors or gas appliances on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

Frequently asked questions

Is Eagles Point Landing pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Eagles Point Landing?

As of Apr 10, 2026, prices found for a 1-night stay for 2 adults at Eagles Point Landing on Jun 26, 2026 start from $1,741, 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?

Onsite parking is available at the property.

What time is check-in at Eagles Point Landing?

Check-in begins at 4:00 PM.

What time is check-out at Eagles Point Landing?

Check-out is at 10:00 AM.

Where is Eagles Point Landing located?

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

Eagles Point Landing Reviews

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 56 out of 61 reviews
Rating 8 - Good. 5 out of 61 reviews
Rating 6 - Okay. 0 out of 61 reviews
Rating 4 - Poor. 0 out of 61 reviews
Rating 2 - Terrible. 0 out of 61 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Shaama P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great vacation

Great!
Stayed 12 nights in Aug 2024
Verified

10/10 Excellent

Bryan A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet vacation retreat

We were looking for a quiet break this summer, and Beth's property delivered. The pool was a big hit, and on rainy days we explored the area which had plenty of options.
Stayed 6 nights in Jul 2024
Verified

10/10 Excellent

Abigail S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A perfect trip

Thank you so much for a great stay. We enjoyed the paddle boards, the fire pit, the grill, and the pool. What a lovely place-- wish we could have stayed longer.
Stayed 2 nights in May 2023
Verified

10/10 Excellent

Luke M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful spot

My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again.
Stayed 3 nights in May 2024
Verified

10/10 Excellent

Aulo G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful!

Wonderful stay in wonderful farm for family of 5 by the river- very relaxing, great swimming pool and walks on the farm, in lovely home with amazing views. Dog had a great time too!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Anita H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing stay

We were looking for a quiet vacation to rekax and regroup. The house and property provided just that. We were close enough to Cestertown and surrounding towns but far enough away to enjoy the quiet. Beth was an amazing host.
Stayed 6 nights in Aug 2024
Verified

10/10 Excellent

Matt B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun

Beautiful and huge property. Paddling in the river was great!
Stayed 3 nights in May 2024
Verified

8/10 Good

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing retreat

Good location. House well stocked. Great pool. Short hike to river. Lots of kayaks ,a canoe and paddle boards
Stayed 4 nights in Jun 2024
Verified

10/10 Excellent

Dave K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family getaway

Our family of 5 had a wonderful stay. The property and location was just what we needed to “get away from it all” for a week. We enjoyed boating on the river and visiting the town for dinners, but the best part was just spending quality time together on the property (and of course the convenience of being able to play tennis and basketball and then just walk over to the pool and relax). Beth was a wonderful host and her communication leading up to our trip was excellent. We would definitely recommend!
Stayed 4 nights in Jul 2023
Verified

10/10 Excellent

Mary P.

Liked: Check-in, communication, location, listing accuracy

Relaxing getaway at a beautiful property

We truly enjoyed our stay at this beautiful property. Everything you need is here and you can’t beat the seclusion. There’s something for everyone to do. The pool and sport court were by far our favorite parts. They’re in great condition and we got a ton of use out of them. The house was perfect for our group of 7 and Beth was very responsive and helpful.
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Jeff S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great getaway in secluded location

Had an excellent time at this beautiful and secluded property on the Chester River. Although very private and a lot of outside space to roam, we were still very close to all that Chestertown has to offer. So, it was the best of both worlds. Plenty of amazing scenery and wildlife to enjoy around the property, and Beth is an excellent communicator. If you're a wine drinker, check out a number of close-by wineries like: Casa Carmen, Bu-De, Broken Spoke and Crow Vineyards. Would highly recommend this property!
Stayed 3 nights in Nov 2023
Verified

10/10 Excellent

James K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing property!

Stayed here over Mem Day weekend with my family of four and two other couples. The house layout was perfect as the top floor has two bedrooms with bathrooms and so does the bottom floor. We spent all weekend enjoying the property which is just massive. Between the pool, boat house with kayaks and canoe, expansive lawn and sportcourt we were entertained throughout. The kitchen is fully stocked and the views from the living room/kitchen were just divine. Beth the property owner was super responsive and helpful and the town of Chestertown is an absolute delight.
Stayed 3 nights in May 2023
Verified

10/10 Excellent

JOANNA L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A Pleasure!

Beth's property is a beautiful spot - even in not the best of weather! Our family group of 8 adults was very comfortable there. The layout of the house gives privacy for all with spacious gathering areas as well, all with lovely pastoral views and glimpses of the river. We lacked nothing and Beth was very accommodating! It is very serene, peaceful, and private. Lots of activities available on the property also but we unfortunately did not have much time or nice weather for outside. We did enjoy a quiet, well thought out and relaxing space to reunite with family.
Stayed 3 nights in Apr 2023
Verified

8/10 Good

Sherri A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

NJ visits Maryland

The property amenities were terrific including the sports court, pool and the river access including the canoe, kayaks and paddle boards. The privacy of the property and walks to the dock were enjoyed by the family and our dogs. Boys enjoyed fishing off the dock as well. The house is a bit older as seen in the pictures but the kitchen and family room were spacious and we enjoyed many meals, board games and card games around the kitchen table. Bring your bug spray for your family and pets as you will need it. Hosts were very responsive and tended to any questions very quickly . Definitely a memorable family vacation.
Stayed 5 nights in Aug 2024
Verified

10/10 Excellent

Karen C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Something for Everyone

Our family's second stay at Eagle Point Farm was just as magical as our first back in June of 2021. I am in agreement with several other reviewers when I admit that part of me wants to keep this hidden gem a secret! There truly is something for everyone here in any kind of weather—from the lovely house (and its well-stocked library) to the peaceful, secluded lawn (with its beautiful shade trees and pool), to the private dock and kayaks. My parents, brother, sister-in-law, nephews, husband, and I filled our days with biking, fishing, swimming, relaxing on the porch, visiting farmers markets, and exploring the shops and architecture of Chestertown. We are grateful that Beth and her family continue to open their home to all of us and look forward to future stays.
Stayed 7 nights in Jul 2024
Archival

10/10 Excellent

Richard & Jane H.

Sailing Backup

We are three retired couples who have met annually for many years to sail on the Chesapeake. This year we rented rather than stay at hotels or B&B's and hope to return for many years to come. Without wind on two of our four days, we discovered kayaking on the beautiful Chester River, enjoyed the pool, the deck, and this perfectly outfitted home. We have rented through VRBO throughout the U.S. and Europe and found this home to be truly exceptional. We found everything we could possibly have wanted except for wash clothes (we assumed the owners are European) and an extra large cooking pot for crabs or paella (we made do anyway).
Verified

10/10 Excellent

Portia W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect peaceful getaway!

My husband and I stayed here for a week with our three children (ages 7, 5, & 5). There was plenty to do between the pool, canoeing on the river, and the tennis/pickleball court! And when the kids got antsy, town was only 15 minutes away, with ice cream, restaurants, and cute shops. The house was BEAUTIFUL! Everything was clean and well maintained, and the a/c was in perfect working order. Definitely be prepared for wild life, we found several frogs, birds, salamanders, and a giant snake skin. This home is ideally situated between NYC/Philadelphia and DC, which made it great for bringing two different groups together. I only wish one of the bedrooms had bunk beds so we could come back with a larger group! :) We had a wonderful stay, and would recommend it to anyone looking for a quiet retreat.
Stayed 7 nights in Aug 2023
Archival

10/10 Excellent

Lex M.

Awesome Sauceum

If you need to get away and relax for a week or weekend this is the place to go. The house was very nice, clean and stocked with everything we needed. The views are many. It may be the river, farm, moonlit sky or all of natures finest. We saw deer, eagles, osprey, herrons, etc. The walk to and from the river is also a nice stroll and very peaceful. The swimming pool is awesome, big and clean. Sit and chill downstairs on the patio or upstaires on the deck which is loaded with tables and chairs. Inside the home has a big great- room, kitchen, dining combo. Pretty hardwood floors in most of the home and comfy bedrooms with private baths and a down stairs living room makes for a very comfortable stay. Did not get a chance to use the boat dock or kayaks. Will return for a longer stay. Thank you Beth for sharing your home with my family Lex
Archival

10/10 Excellent

Lisa D.

Can't wait for next year!

What a wonderful week we had on the Eastern Shore. House was fully equipped with all the necessities, with gorgeous views abound! Our family loved the pond in the back (where the boys could be found fishing at any time of the day) and the pool was just spectacular. The only time we ever left the house was to take a quick drive into town to get ice! The location is extremely private which is just what we were looking for. Our only complaint is that the glass sliding doors on the top floor were impossible to open. If they were usable, we would have spent more time on the gorgeous balcony. Also, we were unable to locate any outside lights for the backyard, which would have made for wonderful evenings out back. Hopefully, these things will be fixed in time for our 2015 stay! Thanks for a wonderful week!
Verified

10/10 Excellent

Howard G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hidden Gem

It's an age-old question, do you let people know about a hidden gem or not? My wife and dog have stayed at this house for 5 to 6 weeks over the last two years during September and October. It has been a fantastic experience. The property is close to town but still offers a quiet, rural setting. Zoey, our dog, loves it—it might be her favorite place on earth, with plenty of space to play, chase tennis balls and when she gets too hot, she has easy access to a river to cool off. The property has a great pool, long enough for casual lap swimming and a well-kept tennis/basketball court. The house has relaxed, comfortable, high-quality furniture that makes it feel like a home away from home with a broad selection of reading materials from histories to thrillers to Shakespeare. It's an ideal spot for a relaxing getaway with enough internet bandwidth to get some work done if you need to or watch some TV if you don't. You should be aware the house is on a farm so there will be nature: some harmless snakes, lots of bird noise, curious deer, the occasional raven, and insects.
Stayed 18 nights in Sep 2023
Verified

10/10 Excellent

Aulo G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay in a beautiful corner of the world

We are a family of 5 who have enjoyed our stays at Eagle Point farm- it's been three times now and it's just wonderful!
Stayed 9 nights in Aug 2022
Verified

10/10 Excellent

James W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great House!

Overall the house was great. Everyone that stayed said the same thing upon checking in and that was the pictures do not do the house justice! We had 3 couples and 2 other people staying and we all fit perfectly. Each bedroom has its own bathroom connected to it which was great for everyone. Common area was large and the pool is huge and well maintained. Short walk on the property takes you to the dock which they have stocked with kayaks and a canoe which we used and all equipment was in great shape. Tennis court/basketball court were also nice additions to have. Property is located way off the road and you are fairly secluded which leads to great privacy. Would highly recommend this place for anyone looking to stay with a family, or group of friends. Host was also super helpful along the way!
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Lane W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

BEST TRIP EVER!

I am so grateful to have had the opportunity to experience this place! Beth couldn’t have been more helpful and accommodating! The property is a gem…wide open with a perfect view of the river, yet private! It’s a nature lovers dream. I was impressed by the native landscape and conservation efforts. I think there is a lot of history here and I feel so fortunate we were able to experience this special place! And the beds were SO comfortable!!!!
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Julie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely and peaceful get-away

We really enjoyed our stay. The house has everything you need!! Just bring yourselves. Thank you!!
Stayed 14 nights in Jul 2022
Verified

10/10 Excellent

Sid I.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fall getaway

Our group of four adults had a very nice time at Beth’s house. The property is beautiful and well taken care of. Beth herself is very responsive and a delight to work with. We would love to return,
Stayed 3 nights in Oct 2021