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Waterfront, Stylish, Historic Retreat

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Everything You Need for Dining in Style.

Everything You Need for Dining in Style. Watch Tall Ships from your dock. This is Our Favorite Spot for River Watching. Start Your Day with Tea in the Sun. The Spacious, Sun Filled Kitchen is Fully Equipped. The Kitchen Table Seats up to 8 Guests. Watch the Sunrise Over the River from the Master Bed. The 'Winter Room' is Wonderful for Reading by the Fire. A Perfect Setting for Cocktails Before Dinner in Town. The Second Bedroom Doubles as a Zen-Like Retreat. Watch from the Porch as the Tall Ships sail by A View from the Porch; Sunset Lights the Bridge. Waiting for Sunset, the view from the Porch Contemplate the Changing Light from the Porch.

Calendar

Last updated: 04/15/2014
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:2 nights
  • Internet:Yes
  • Pets considered:Ask Owner
  • Wheel chair accessible:No

Chestertown condo description

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...

Keywords: Waterfront, Historic House, Vacation Flat, 1.5 Bedroom Condo

Property Type

  • On floor 3
  • 1100 sq. ft.
  • 1 story
  • Condo

Accommodation Type

      • Vacation Rental

      Meals

          • Guests Provide Their Own Meals

          Suitability

          • Non Smoking Only
          • Long-Term Renters Welcome

          Bedrooms: 2 Bedrooms, Sleeps 3, Beds for 2-3

          Bathrooms: 2 Bathrooms

          Kitchen & Dining

          • Dining:

            Dining in the large kitchen overlooking the river. Additional dining on porch overlooking the river and in the winter room (seats 4). ...moreless

          • Dining Area Seats:

            6...moreless

          • Kitchen
          • Cooking Utensils
          • Microwave
          • Ice Maker
          • Dishwasher
          • Dishes & Utensils
          • Stove
          • Coffee Maker
          • Refrigerator
          • Toaster

          Amenities

          • Clothes Dryer
          • Linens Provided
          • Washing Machine
          • Gas Fireplace
          • Air Conditioning
          • Hair Dryer
          • Heating
          • Fireplace
          • Towels Provided
          • Living Room
          • Parking

          Entertainment

          • Stereo
          • CD Player
          • Satellite / Cable
          • Television
          • DVD Player

          Communications

          • Wireless Internet
          • Internet

          Outdoor Features

          • Balcony
          • Deck / Patio
          • Lawn / Garden
          • Outdoor Grill

          Theme

          • Sports & Activities
          • Romantic
          • Historic

          Location & View

          • Water View:

            Riverfront views from Master Bedroom, Kitchen, Porch and Dock...moreless

          • Waterfront:

            Directly on the Chester River with Dock...moreless

          Car

              • Not Necessary

              Activities

              • Massage Therapist
              • Hospital
              • Fitness Center
              • Medical Services
              • Antiquing
              • Sight Seeing
              • Groceries
              • ATM/Bank
              • Hunting
              • Water Skiing
              • Kayaking
              • Hiking
              • Cycling
              • Sailing
              • Golf
              • Fishing
              • Museums
              • Cinemas
              • Restaurants
              • Live Theater
              • Library
              • Churches
              • Winery Tours
              • Marina
              • Shopping
              • Walking
              • Boating
              • Wildlife Viewing
              • Eco Tourism
              • Bird Watching
              • Scenic Drives
              • Paddle Boating

              Other Activities

                  • Washington College Cultural Life, Historic Tours, Architectural Tours
                   

                  Reviews

                  Write a review
                  • Reluctantly Honest Review

                    Reluctantly Honest Review

                    • Guest WACParent
                    • Date of stay 04/04/14
                    • Review Submitted 04/09/14
                    It is with great regret that we review this property. With a lot of years visiting Chestertown left ahead of us, we'd have greatly preferred to keep 105 Water Street a secret. The highest compliment we can pay this property is that it exceeds expectations. As appealing as the posted photos make it seem, we found the unit to be larger and brighter, much closer to the water than it appeared in the photos and the dock access (and small yard in front of that) to have been undersold. The property owner could not have been better to deal with, the location (a few blocks from the bakery and restaurants, around the corner from the boat landing, just the right buffer from the College) is perfect and we wanted for nothing in terms of spotless dishes, utensils and the like. While we couldn't recommend it more highly, we're really hoping readers don't steal the future dates we need...

                    Recommended for: Families with teenagers, age 55+, sightseeing, romantic getaway, tourists without a car.

                    Did you find this review helpful? Yes | No Helpful votes: 0/0

                  • step back in time with all the modern conveniences

                    step back in time with all the modern conveniences

                    • Guest Youngs
                    • Date of stay 03/25/14
                    • Review Submitted 03/29/14
                    One is almost surprised to find state of the art conveniences in this elegant condominium located on the top floor of a historic house. The views of the river are ever changing and ever engaging, and the condo itself was pristine and welcoming. Wonderful restaurants and Evergrain, a fabulous bakery, are only steps away in the heart of historic Chestertown, and the inhabitants uniformly helpful, interesting, and welcoming. Our hostess was responsive and informative. We will be back!

                    Recommended for: Families with teenagers, age 55+, girls getaway, sightseeing, romantic getaway, tourists without a car.

                    Did you find this review helpful? Yes | No Helpful votes: 0/0

                  • Exceptional place

                    Exceptional place

                    • Guest Debi T.
                    • Date of stay 12/14/13
                    • Review Submitted 12/18/13
                    This is a very nice, comfortable condo overlooking the chester River. Awesome place to stay in the heart of the historic district. The deck overlooking the River was very spacious and beautiful. I recommend this place to everyone.

                    Did you find this review helpful? Yes | No Helpful votes: 1/1

                  • Robin

                    Robin

                    • Guest Robin (Florida)
                    • Date of stay 09/01/12
                    • Review Submitted 11/03/12
                    The accomodations are lovely..the location is ideal as you can walk anywhere you really need to go. Owner is more than willing to do whatever to see your stay is enjoyable

                    Recommended for: Age 55+, girls getaway, sightseeing, romantic getaway, tourists without a car.

                    Did you find this review helpful? Yes | No Helpful votes: 2/3

                  • Great Place

                    Great Place

                    • Guest bj (langhorne PA)
                    • Date of stay 05/25/12
                    • Review Submitted 05/30/12
                    I can't say enough how pleased I was to wind up at 105 water street for a weekend getaway. The condo is very nicely decorated and in pristine condition. The layout is spacious and comfortable and the view of the river is as good as it gets. This place is a winner.

                    Recommended for: Girls getaway, romantic getaway.

                    Did you find this review helpful? Yes | No Helpful votes: 3/4

                  • Beautiful Place

                    Guest comment entered by owner

                    Beautiful Place

                    • Guest Beth & John
                    • Date of stay 05/18/12
                    • Review Submitted 05/24/12
                    We just wanted to let you know how much we enjoyed our visit to Chestertown. Your condo is just beautiful and the view from the porch breathtaking! We absolutely loved staying there, It was almost too difficult for us to venture into town! The weather was fantastic, we couldn’t have asked for more. Thank you again for opening up your beautiful home to travelers.

                    Did you find this review helpful? Yes | No Helpful votes: 1/1

                  • Beautiful property, attentive landlord

                    Beautiful property, attentive landlord

                    • Guest AB (Key West)
                    • Date of stay 09/09/11
                    • Review Submitted 09/25/11
                    I stayed in this third floor condominium -- located in an historic, quiet building w/ a lovely view -- with two friends over a long weekend. The unit was immaculately clean, well-tended and appointed, with an adorable deck and a well-quipped kitchen. Plenty of room for all three, and a very short, delightful walk to downtown Chestertown's fresh bakery, farmer's market, quaint restaurants, natural foods store and kayak/bike rental company. Within short driving distance to other numerous attractions: eco-tours, horseback riding, kayaking, sailing, etc. The landlord was accomodating not only pre-stay and during our stay, but also afterwards with a quick return of deposit and note. Comfortable and no hassle.

                    Recommended for: Girls getaway, sightseeing, romantic getaway, tourists without a car.

                    Did you find this review helpful? Yes | No Helpful votes: 3/3

                  • Retreat

                    Guest comment entered by owner

                    Retreat

                    • Guest KO
                    • Date of stay 05/28/11
                    • Review Submitted 08/31/11
                    Thanks so much for the rental of your condo. The location was perfect. My friends live two doors down, so it was practically like staying with them while having my own place to retreat to.

                    Did you find this review helpful? Yes | No Helpful votes: 0/0

                  • Early Spring

                    Guest comment entered by owner

                    Early Spring

                    • Guest Blake
                    • Date of stay 03/01/11
                    • Review Submitted 08/31/11
                    Brilliant sun here today. At Against The Grain we had lunch, bought lots of bread/goodies and met some lovely local people. Your condo...so beautiful...so clean. We've gotten lots of reading done, had some good walks and saw snowdrops, so all around...a good visit. Your Chestertown home is absolutely beautiful. We loved the interior design.

                    Did you find this review helpful? Yes | No Helpful votes: 1/1

                  • A 10!

                    Guest comment entered by owner

                    A 10!

                    • Guest DBJ
                    • Date of stay 10/15/10
                    • Review Submitted 08/31/11
                    #6 Water Street Rates a "10" In My Book Thank you for providing us with such a great place to "get away" and "connect". We arrived early enough on a Friday afternoon to enjoy an Indian Summer sunset while enjoying wine and cheese on the end of the dock, complete with a backdrop of geese landing to rest on the river. Taking a steer from you, we had a thoroughly enjoyable dinner at Blue Heron Cafe, and were pleased with ourselves for having called ahead to reserve a table. Paul's place is very popular! Seeing the warm morning sunshine streaming through the bedroom window was a perfect way to start a Saturday which we spent poking around in shops in C'town, visiting the historic Customs House, and the touring the waterfront. Later on we walked to the Imperial Hotel, a delightful place for a drink at the bar and dinner and enjoyed our short stroll 'home' under starry skies. We saved our own cooking effort for Sunday morning breakfast -- easily done in a kitchen that is well equipped. It was fun to cook and watch boats float by at the same time. The porch overlooking the river is a very relaxing place to dine, river-watch, and catch up with a 'big city' newspaper we bought on an early morning walkabout in town. Our only regret was having to pack up and drive away from this really pretty spot. However, you can count on having us back again...and again. We want to see all the seasons there.

                    Did you find this review helpful? Yes | No Helpful votes: 3/3

                   
                  Rental basis: Per property
                  Dates Nightly Weekend Night Weekly Monthly * Event
                  High Season
                  Apr 1 - Nov 1, 2014
                  2 night min stay
                  $260 $260
                  Thu, Fri, Sat, Sun
                  $1,600 $4,500
                  My Standard Rate
                  2 night min stay
                  $240
                  $1,000 $3,000
                  * Approximate Monthly rates, actual rate will depend on the days of the month you stay

                  Additional information about rental rates

                  Fees:

                  • Refundable Damage Deposit $300
                  • Pet Fee $50 + tax
                  • Tax Rate 11%

                  This owner accepts HomeAway payments.
                  Always use this free service to protect your payments up to $10,000 against fraud while keeping your financial information private. With HomeAway Payments, your credit card information is not seen by the owner or manager. NEVER pay by cash or instant money transfer services such as Western Union or MoneyGram. Call the owner to confirm booking request.


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                  Calendar

                  Last updated: 04/15/2014
                  Check availability
                  23 Available
                  21 Unavailable
                  22 Today
                  23 Selected dates
                   

                  Location

                  • Nearest Barpub: The Imperial Hotel at 0.2 Miles
                  • Nearest Restaurant: The Imperial Hotel, Blue Heron, at 0.2 Miles
                   

                  Owner info

                  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.


                  Contact us

                  Speaks: english

                   

                  Photos

                  • Everything You Need for Dining in Style.

                    Everything You Need for Dining in Style.

                  • This is Our Favorite Spot for River Watching.

                    This is Our Favorite Spot for River Watching.

                  • The Spacious, Sun Filled Kitchen is Fully Equipped.

                    The Spacious, Sun Filled Kitchen is Fully Equipped.

                  • Watch the Sunrise Over the River from the Master Bed.

                    Watch the Sunrise Over the River from the Master Bed.

                  • A Perfect Setting for Cocktails Before Dinner in Town.

                    A Perfect Setting for Cocktails Before Dinner in Town.

                  • Watch from the Porch as the Tall Ships sail by

                    Watch from the Porch as the Tall Ships sail by

                  • Waiting for Sunset, the view from the Porch

                    Waiting for Sunset, the view from the Porch

                  • Watch Tall Ships from your dock.

                    Watch Tall Ships from your dock.

                  • Start Your Day with Tea in the Sun.

                    Start Your Day with Tea in the Sun.

                  • The Kitchen Table Seats up to 8 Guests.

                    The Kitchen Table Seats up to 8 Guests.

                  • The 'Winter Room' is Wonderful for Reading by the Fire.

                    The 'Winter Room' is Wonderful for Reading by the Fire.

                  • The Second Bedroom Doubles as a Zen-Like Retreat.

                    The Second Bedroom Doubles as a Zen-Like Retreat.

                  • A View from the Porch; Sunset Lights the Bridge.

                    A View from the Porch; Sunset Lights the Bridge.

                  • Contemplate the Changing Light from the Porch.

                    Contemplate the Changing Light from the Porch.

                  VRBO #328116

                  There have been  visitors to this page since the counter was last reset in .

                  This listing was first published here in 2010.

                  Date last modified - Friday, January 17, 2014

                  $240 - $260 per night (USD)
                  10

                  2 Bedroom / 2 Bathroom
                  Sleeps 3

                  View calendar: Updated 04/15/14
                  Minimum stay: 2 nights
                  Dates are unavailable
                  Please stay a bit longer. A stay of nights or more is required for these dates.
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                  Owner
                  Email owner

                  (302) 528-4659

                  Speaks: english
                  This owner accepts HomeAway Payments. Always use this free service to protect your payment up to $10,000 against fraud while keeping your financial information private.
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