VRBO is part of the HomeAway family, the world leader in vacation rentals with over 1 million listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More
Directly on the Chester River in the historic district, this 1800's house is beautifully restored. #6 is the top floor condominium and has spectacular waterfront views. This condo is located on the famous Water Street block of the Historic District, which features the finest architectural/historic homes of Chestertown. This is a perfect location from which to enjoy cultural events, water sports, fishing, and sightseeing. Park your car and walk -- this is the heart of Town!
A 25' boat slip is included. Bring your boat, or tie up your kayaks and take to the water! The Chester River is rich with wildlife and peaceful shorelines.
The condo is beautifully decorated, well equipped and newly renovated. All the furnishings and utensils are new and clean. There is no owner clutter! The gourmet kitchen has granite countertops, top of the line appliances, a sunny orientation and a gorgeous, open view of the Chester River. Take your coffee to the porch and watch Osprey fish and feed their young, view classic and historic boats, and have a front row seat as the Tall Ships sail by. Watch the sunrise from the master bedroom. Take a seat on the dock at sunset and watch as the sky blooms with color. Walk into town for a delicious dinner then head back to the dock for spectacular stargazing. Or stay in and whip up a fabulous Eastern Shore feast in the fully equipped kitchen and enjoy your private dinner on the river.
Take in the cultural and historic offerings of Chestertown; Washington College, art galleries, architectural and historic tours, as well as every boating activity the Eastern Shore has to offer. The marina is a block away. Book a sail on the Sultana (which you can see from the porch!) Rent kayaks & bikes which are a short walk away. Try the exceptional local restaurants (The Imperial Hotel & Blue Heron Cafe are favorites). Don't miss the Farmer's Market. Chestertown is the Eastern Shore at its finest!
Southern Living Magazine calls Chestertown, 'one of our all-time-favorite small towns' in an article called 'Chesapeake Charm,' by Annette Thompson, Southern Living, July, 2008. 105 Water Street is in the centerfold photograph! Come visit this beautiful place...
* Approximate Monthly rates, actual rate will depend on the days of the month you stay
Additional information about rental rates
Pet Fee$50 + tax
Refundable Damage Deposit$300
Cancellation policy: $300 cancellation fee if booking is canceled within 2 weeks of date of arrival.
Pay with confidence
Paying through this free service protects your payment up to $10,000 against listing fraud. If you are not paying through HomeAway Payments always call the owner at the number listed on our website and never use instant money transfer services such as Western Union and MoneyGram.
Adding our Vacation Protection services can make sure your getaway goes smoothly, no matter what. We offer Cancellation Protection, Carefree Rental Guarantee, and Damage Protection so you can truly relax.
Protect your payments in case you need to cancel.
Guarantee the rental meets your expectations.
Ensure you're prepared in case of accidental damage.
Washington College Cultural Life, Historic Tours, Architectural Tours, bike and kayak rentals, tall ship & historic boat tours. Skeet & trap, golf nearby.
Year Purchased: 2006
About the owner: We've always enjoyed the Eastern Shore with its wide open spaces, waterways, and beautiful boats. Watching the light on the river is wonderfully relaxing and restorative. We hope that you'll love it as much as we do.
Why the Owner Chose Chestertown: This property is beautiful, well equipped, and perfectly situated IN town and ON the river. Watching wild life from the porch in an historic house, anticipating the short, delightful walk to the local eateries; that's the good life! Chestertown is a quintessential, historic town that is perfectly positioned in the Mid-Atlantic region. It's an easy drive from Washington, D.C., Baltimore, and Philadelphia.
The Unique Benefits at this Condo: The Chester River is right off the porch and yet you are in the heart of Chestertown. Park your car and leave it. The Saturday morning Farmer's Market is the oldest in the region. There are countless musical performances, cultural gatherings, and art offerings. Make sure you check out Play it Again Sam, for coffee and conversation and The Mainstay, for first rate musical performances.