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Book Online or call HomeAway Booking Assistance +44-800-085-3815

Historic Retreat With River, Garden And Marina Views

7 Reviews
Bedrooms 3
Property type house
Minimum Stay 3 nights

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Minimum Stay
3 nights


Photos and Description of this 3 bedroom holiday home in Chestertown

3 Bedroom, 2 Bathroom, 6 Sleeps

Located on renowned Water Street within Chestertown’s historic district, this early 1900s row house has views of the picturesque Chester River, historic Hynson-Ringgold garden and stately 18th and 19th century mansions.

Just steps from the town center, dock, and marina—and surrounded by some of the finest historic architecture in Maryland—you can park your car in our private drive and discover all Chestertown has to offer. Stroll brick-lined streets that take you back to the time of George Washington or visit Chestertown’s many contemporary specialty shops, galleries, cafes and fine restaurants. Enjoy a variety of cultural and historic events at Washington College or take in a live performance at the Prince Theater.

Want to get out on the water? Book a sail on the historic schooner, Sultana, berthed within view of your house or take a dinner cruise on the riverboat, Packet, departing just steps from your back garden gate. For nature lovers eager to explore the quiet river or countryside, rental kayaks and bikes are available a short walk away.

Many of Chestertown’s special events occur right outside your door, including the spirited Tea Party Festival, renowned Chestertown Jazz Festival and popular “Downrigging Weekend.” Don't miss the farmer and artisan’s market every Saturday or fun First Friday’s each month.

"Chestertown is a treasure hidden in plain sight," said Richard Moe, president of the National Trust for Historic Preservation. "A small, historic and relatively unspoiled Eastern Shore town, Chestertown had the good sense to hang on to what makes it so special. The result is a vibrant community that offers travelers an ideal retreat."

This three-story, three bedroom row house is comfortably furnished with everything you need to enjoy your stay, including a fully equipped kitchen. Situated behind the town’s riverwalk and directly next to a historic garden, it’s a private oasis where natural light fills every room. Relax on one of three porches. Two rear porches offer both sunrise and sunset river views, while a front porch invites you to sit and indulge in a favorite Eastern Shore pastime—watching the world go by.

More Details
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible

Robin and Richard
Member since: 2015
Speaks English
Response time:
Within 12 hours
Response rate:
Calendar last updated:
21 October, 2016

About Robin and Richard

One owner is a graduate of Washington College; the other is a Lehigh University alum. Both have fallen under the spell of this enchanting, small town.

Robin and Richard purchased this house in 2004


based on 7 holidaymaker reviews

Historic Retreat With River, Garden And Marina Views
average rating of 5.0 based on 7 reviews

A wonderful house in a perfect location = a lovely weekend with friends and family

  • 5 of 5

The house is located on the Chester River and in the heart of Chestertown so the location is perfect and the views are grand. We especially appreciated the 2nd floor balcony - so relaxing to look out over the river! The house is well decorated and comfortable; the kitchen nicely updated. All in all, a very nice place to stay.

Our hosts also were welcoming and made certain that everything was in place. They were very patient with us when we could not find the second set of keys. Thanks to them, we finally found the keys and proceeded with a weekend full of good memories.

  • Review Submitted: Oct 4, 2016
  • Date of Stay: Sep 2016
  • Source: VRBO, from HomeAway
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First class

  • 5 of 5

Everything was as promised. The property was extremely clean and well kept. Even the basement is clean. It feels like a home, not a rental property.

The screened in porch off of the second floor bedroom is a real treat. You will be walking distance to most places you would want to go, and a short drive to Washington College. The wifi works very well. I can confirm that the bed in the second floor bedroom is very comfortable.

This is a first class property, well run and comfortable.

  • Review Submitted: Oct 2, 2016
  • Date of Stay: Sep 2016
  • Source: VRBO, from HomeAway
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Great House and Location

  • 5 of 5

We spent the summer here and found the house and location to be very enjoyable. The house has all the comforts of home and is within walking distance of shops, restaurants and the many other amenities that Chestertown and Kent County have to offer. The owners were great to work with. Highly recommended!

  • Review Submitted: Sep 22, 2016
  • Date of Stay: May 2016
  • Source: VRBO, from HomeAway
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excellent rental property

  • 5 of 5

The rental property was absolutely wonderful for getting ready for our daughter's wedding. The house was beautifully decorated, spacious and immaculate. The location of the house was perfect, so close to town and beautiful scenery and parks. Thank you for allowing us the opportunity to rent you home. Sandy and Tim

  • Review Submitted: Sep 18, 2016
  • Date of Stay: Aug 2016
  • Source: VRBO, from HomeAway
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Perfect Chestertown House!

  • 5 of 5

I spent the weekend at this sunny, beautiful house! My son got married in Chestertown and it was the perfect location to get to all the in-town wedding activities. The kitchen & breakfast area are perfect for morning coffee - and all meals. The main level space is open & bright! All of the bedrooms are comfortable & well appointed & the bathrooms are clean and big! I love the sitting room on the second floor! The screened in porch on the second level has a lovely view of the water & the small deck off the kitchen is cozy & comfortable too! If you are looking for a get-away place in Chestertown - this is it!! You can literally get any place in town in minutes - & you are right on the water - which is wonderful!

  • Review Submitted: Sep 12, 2016
  • Date of Stay: Sep 2016
  • Source: VRBO, from HomeAway
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Thoroughly Delightful!

  • 5 of 5

In Chestertown for a long weekend for our son's graduation over the weekend. We found this lovely property on the Home Away site. The home is immaculate, charming and elegantly appointed. Our only regret is that we didn't know about it before, or we definitely would have rented previously. We recommend this property to anyone looking for a beautiful home, in a beautiful setting with a quaint porch and view of Chester River from nearly every room.

  • Review Submitted: May 25, 2016
  • Date of Stay: May 2016
  • Source: HomeAway
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Washington College
Fountain Park
Chestertown Marina
Prince Theatre
Car: necessary


Prices & Availability

Prices for this holiday house in Chestertown, Chesapeake Bay

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly * Event Price
Downrigging weekend
28 Oct 2016 - 30 Oct 2016
3 night minimum stay
Washington College Graduation
18 May 2017 - 20 May 2017
3 night minimum stay
Tea Party Festival
26 May 2017 - 28 May 2017
3 night minimum stay
My Standard Rate
3 night minimum stay
for 3 nights

Additional pricing information

Cleaning fee £123
Refundable Damage Deposit £328

Payment will be refunded in full if booking is cancelled within 30 days of rental start date.

Owner's Cancellation Policy

  • 50% refund for cancellations more than 30 days before check-in date.
  • 100% refund for cancellations more than 60 days before check-in date.
Enter dates for accurate pricing
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Available arrival


Accommodation and facilities for this holiday house in Chestertown in Maryland

Property Type:
  • house
  • Self-catering
Location Type:
  • city centre
  • village
  • Water View
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace ...
  • Hair Dryer
  • Heating ...
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Parking ...
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils ...
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven ...
  • Pantry Items ...
  • Refrigerator
  • Hob ...
  • Toaster
  • Dining
  • Dining Room
  • seating for 6 people
  • 2 Bathrooms
  • Bathroom 1 - Toilet , Bath with Shower , 2nd floor
    Bathroom 2 - Toilet , Shower Enclosure , 3rd floor
  • No bathroom on first floor
  • 3 Bedrooms, Sleeps 6
  • Bedroom 1 - 1 Large Double Bed , with screen porch
    Bedroom 2 - 1 Large Double Bed
    Bedroom 3 - 2 Single Bed
  • Books
  • DVD Player
  • Games ...
  • Satellite / Cable
  • Stereo ...
  • Television
  • Video Library
  • Balcony
  • Terrace ...
  • Garden ...
  • Barbecue ...
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters ...
  • children welcome
  • non smoking only
  • pets not allowed
  • wheelchair inaccessible
  • churches
  • cinemas
  • festivals
  • library
  • live theatre
  • marina
  • museums
  • playground
  • restaurants
  • winery tours
Leisure Activities:
  • antique hunting
  • bird watching
  • Boating
  • photography
  • Shopping
  • sight seeing
  • walking
  • Wildlife Viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • laundrette - serviced
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • hiking
  • hunting
  • Kayaking
  • pier fishing
  • sailing
  • swimming

Partner Offers

Portable wifi hotspot

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