HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled
Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992
Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992

Historic Retreat With River, Garden And Marina Views

Bedrooms 3
Property type house
Minimum Stay 3 nights


About the property

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

Robin and Richard
Member since: 2015
Speaks English
Response time:
Within 12 hours
Response rate:
Calendar last updated:
7 October, 2017

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


Accommodation and facilities for this holiday house in Chestertown in Pomona

Property Type:
  • house
  • Self-catering
House Rules:
  • Check-in: 16:00 / Check-out: 11:00
  • Max. occupancy: 6
  • Minimum Age Limit for Renters ...
  • children welcome
  • pets not allowed
  • non smoking only
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
  • 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


Exceptional! 5/5 -
(9 traveller reviews)

100% Complete
0% Complete
0% Complete
0% Complete
0% Complete
Historic Retreat With River, Garden And Marina Views
average rating of 5.0 based on 9 reviews


  • 5 of 5

The house was clean, well maintained and ideally located. It was an absolutely wonderful place to relax and recharge.

  • Review Submitted: Oct 1, 2017
  • Date of Stay: Sep 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

Charming historic home and fantastic location to enjoy beautiful Chestertown!

  • 5 of 5

Perfect location for our 3 couples in town for a wedding. Highly recommend this!

  • Review Submitted: Sep 17, 2017
  • Date of Stay: Sep 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

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
Did you find this review helpful?
0 0

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
Did you find this review helpful?
0 0

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
Did you find this review helpful?
0 0

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
Did you find this review helpful?
0 0


Car: necessary


Prices & Availability

Prices for this holiday house in Chestertown, Maryland

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly * Event Price
Downrigging weekend
27 Oct 2017 - 29 Oct 2017
3 night minimum stay
Washington College Graduation
18 May 2018 - 20 May 2018
3 night minimum stay
My Standard Rate
3 night minimum stay
for 3 nights

Additional pricing information

Cleaning fee £112.92
Refundable Damage Deposit £301.12

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.
Enquire Now

You might like these similar holiday rentals