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Chester River House with Views

Bedrooms 3
Half Baths1
Property type house
Minimum Stay 2 - 3 nights


About the property

A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at Washington College in Chestertown - with views no hotel can match!

Our house provides 3 bedrooms, an open dining-kitchen area, one main bathroom and a separate lounge that overlooks the river. All rooms are on the same floor. There are 4 kayaks at the property which are by the private dock and may be used by guests (at your own risk). Life vests are also provided.

There is no public transport in the area, but parking is provided in the front driveway for 3 cars. There is a yard front and rear and a gas grill is available on the deck.

Bedroom 1 has a double bed.

Bedroom 2 has a bunk bed with a twin over a double bed.

Bedroom 3 has a bunk bed with 2 twins.

There is a washer and dryer as well as a 2nd toilet in an attached workshop to the side of the house - which is accessible via a separate locked door from the outside.

More Details

David Kirk
Member since: 2012
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
September 21, 2017

About David Kirk

We are David & Cheryl Kirk, proud parents of 4 children. We are from the UK, but have lived in the US for 15 years now. We love it here and recently became citizens.

Why David Kirk chose Eastern Shore

This is our 'get away from it all' place. It's a place to instantly relax - especially watching the sunset from the dock.

What makes this house unique

There is something about being on the river - and you can see it from the main living room, or as we call it the 'River Room'.


Chestertown House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Max. occupancy: 7
  • Minimum Age Limit for Renters ...
  • children welcome
  • pets not allowed
  • non smoking only
Location Type:
  • Waterfront ...
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Air Conditioning
  • Broadband Access
  • Clothes Dryer
  • Free Long Distance
  • Heating
  • Linens Provided ...
  • Parking Off Street
  • Parking for RV/Boat/Trailer
  • Telephone
  • Towels Provided ...
  • Washing Machine
  • Wireless Internet ...
  • Coffee Maker ...
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Refrigerator ...
  • Stove ...
  • Dining
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • 1 Half Bath
  • Bathroom 1 -
  • 1.5
  • 3 Bedrooms, Sleeps 7
  • Double Beds (1), Twin or Single Beds (1), Bunk Beds (2)
  • Stereo
  • Television ...
  • Toys ...
  • Video Game Console ...
  • Video Library ...
  • Deck / Patio
  • Kayak / Canoe ...
  • Lawn / Garden
  • Outdoor Grill
  • limited accessibility ...
  • churches
  • cinemas
  • live theater
  • marina
  • restaurants
Leisure Activities:
  • bird watching
  • boating
  • shopping
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • laundromat
Sports & Adventure Activities:
  • fishing
  • freshwater fishing
  • jet skiing
  • kayaking
  • pier fishing
  • sailing
  • swimming
  • water skiing
  • water tubing


Excellent! 4.6/5 -
(35 traveler reviews)

62% Complete
34% Complete
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Chester River House with Views
average rating of 4.6 based on 35 reviews

Great fun on the Chester River

  • 5 of 5

My family and I (ages ranging from 2 to 68) all had a wonderful time at this lovely house on the river. The kids had a terrific time playing games in the backyard, fishing off the dock, roasting marshmallows over the firepit, and watching beautiful sunsets every night. The house is nicely stocked with activities - we absolutely loved taking the kayaks out every day and were excited to be able to try out paddleboarding too! Internet and Netflix/Apple TV worked great for movie nights. We really had a great time all week long. Very quiet, peaceful, relaxing spot to get away from it all!

  • Submitted: Aug 28, 2017
  • Stayed: Aug 2017
  • Source: VRBO, from HomeAway
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  • 3 of 5

Being by the river was awesome... sitting out at night with a drink and friends or having coffee in the morning watching a few boats go by. The location was terrific: nice shops/breakfast eateries in Chestertown, just a short drive to Rock Hall and within an hour of St. Michaels and Oxford.

The 1/2 bath (toilet) "in workshop" was a bit rustic with cobwebs, so we didn't use it. The path to the water heater also was full of cobwebs and the light above the heater didn't work so it was hard to see to change the setting as directed. The furniture and bedrooms were comfortable, but we got the sense that just a little more upkeep, both in and out would make the place exceptional. Until then, we felt that it was a bit overpriced (when cleaning/linens charges were added) compared to our other experiences using VRBO.

Overall, a nice place to stay for a short visit and the welcome basket was a nice touch.

  • Submitted: Jul 6, 2017
  • Stayed: Jun 2017
  • Source: VRBO, from HomeAway
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Great little family vacation!

  • 4 of 5

Beautiful views of the river. Tons of fun for the whole family. The kayaks and paddle boards were great. Looking forward to our next trip back to Chestertown.

  • Submitted: Jul 5, 2017
  • Stayed: Jun 2017
  • Source: VRBO, from HomeAway
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  • 5 of 5

This was a terrific rental! We were here for a family wedding being held at Brittland Estates, closer proximity than the hotels. All linens were provided which is a plus. All wedding festivities were in the evenings so we were able to relax on the deck and kayak on the river all day. Clean, comfy and serene! Beautiful views and sunsets. One floor living, (mom is 90) and easy to keep clean! Our only regret is that we only rented it for three days, we did not want to leave!!!!

Thank you David!

  • Submitted: Jun 12, 2017
  • Stayed: Jun 2017
  • Source: VRBO, from HomeAway
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Columbia, MD

Location can't be beat!

  • 5 of 5

Our group was in the area for the Rock Hall Sprint Triathlon. The house was very well stocked with the comforts of home. But the true joy is the wonderful location right on the Chester River. The layout of the house is such that you get gorgeous river views from the dining room or family room. Eating lunch on the deck or grilling outside were awesome. The provided kayaks and paddle boards provided hours of entertainment even though the river was a bit on the chilly side in early June. Evenings were spent around the fire pit making s'mores. Downtown Chestertown is just a short bike ride away. All in all, our group had a wonderful weekend away. Thanks, David!

  • Submitted: Jun 5, 2017
  • Stayed: Jun 2017
  • Source: HomeAway
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Just as pictures and described. Great for our family.

  • 4 of 5

Great location right on Chester River. Clean and comfortable. Had everything we needed. 3 good sized bedrooms with comfortable beds. Kitchen well stocked with dishes and pots/pans. Decor not fussy with nice sailboat/porthole touches. Not a lot of curb appeal on street side but Very nice indoor and outdoor spaces on facing river. Spacious sun room onto deck onto yard onto dock. Kayaks and SUPS. Easy to get into town by foot, bike, or car. All coordination easy and timely. Only potential weakness for some may be just 1 bathroom, but worked just fine for our family if 4. We've stayed almost everywhere in Chestertown over the years. This is very good base, very good value.

  • Submitted: Jun 1, 2017
  • Stayed: May 2017
  • Source: HomeAway
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Car: recommended

Chestertown is a quaint historic town on the Maryland Eastern Shore and boasts unique shops, restaurants as well as supermarkets, bowling alley and a cinema. Along with the historic Washington College, the town focuses around the river, where you can take cruises on the Sultana (a 18th Century Schooner), or eat overlooking the river.

There are 2 boat ramps in nearby marinas, so bring your boat or jetski for additional fun. The driveway is long enough to park a large vehicle with trailer attached (for example a Suburban with trailer for a 24' boat fits easily).


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $120
Additional Guest Fee $10 per person per night
Damage Deposit $500

Rates are subject to change until reservation is confirmed. $10 per person per night charge for more than 4 guests. There is an optional charge of $50 if guest chooses to have linens provided (bedding and towels).

Check-in time is 4pm, check-out time is 11am.

Owner's Cancellation Policy

100% refund if canceled at least 30 days before arrival date.