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Chester River Waterfront, Magnificent Views, Dock, Beach

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Last updated: 07/28/2015
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23 Available
24 Available check-in
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:1-2 nights
  • Internet:No
  • Pets considered:Yes
  • Wheel chair accessible:N/A

Property description

This property offers spectacular views of the Chester River from the Family room, Kitchen, & Dining room, not to mention from the 'L' head on the dock. All the other rooms enjoy a view of a large pond where you can watch Osprey, Eagles & Heron enjoy the fishing site. Most evenings you can listen to the Bull frogs sing. There are 2 large bedrooms(queen beds.)One has views of the river & the other has views of the large pond out front. The family room features a queen sleeper sofa & has the best view of the river. The family room features hardwood flooring, wet bar w/wine cooler, recessed lighting and fireplace. The kitchen & dining area feature an open floor plan with all new ceramic tile flooring, cherry cabinetry, granite counter tops, & a raised bar between the kitchen & dining area. There are double pocket doors into the family room for privacy. There are french doors from the dining area that will go out to a large deck that has a nice cushion patio set. There is a laundry area that includes a stacked washer & dryer. Both bathrooms have also renovated. There is a full living room with a beautiful view of a large pond. Plenty of parking, a small beach, 50' dock w/10X20 'L' head to relax & watch the sunrise or fish/crab. There is also a shared launch(must use 4 wheel drive b/c it is not concrete.) Bar-B-Que grill, (propane not guaranteed) hammock and patio set as well as plenty of Adirondack chairs. Kayaks & paddle boat & boards are available upon request(pls note,we do not have children's life vests.) There is also a fire pit for those cool nights or to just hang out and make smoors. On the side of the house is a horseshoe pit. HUNTERS WELCOME!! For any of you NASCAR fans, we are situated only 40 minutes from Dover Track. We are also 20 minutes from Rock Hall & 45 minutes from Annapolis. 35 minutes from premium outlets in Queenstown.
** Some dates to consider for fun filled family weeks in 2015 season
Chestertown Tea Party 5/22-25, Rock fish tournaments usually early June and mid Sept
7/5 Waterman's day in Rock Hall, 7/3 Fireworks in Rock Hall, 7/4 Fireworks in Chestertown and parade in Rock Hall. All times are great with lots to do but, if you have never been to this part of the eastern shore then these are the best times.
Bettertown days @ Betterton Beach 8/1
8/7-8/9 is pirates weekend in Rock Hall another great time to be had. Lots of people dress up for the event. Sultana down rigging 10/30-11/1, 10/10 is Rock Halls Fallfest.
Every Sat. till noon in Chestertown's Fountain park, is the farmer's market. Lots of times on Fridays or Saturday evenings(in season) they have entertainment in Fountain park. On the first Friday of every month is 1st Friday in Chestertown(all year long). Many stores stay open and have snacks (wine & beer too) and some have entertainment all FREE. Lots of people walking around during these events. A great way to get to know the town.
Wilmer park has events as well. There are concerts, taste of the town to name a few. If you are planning a certain week and would like to know the events near town, just ask and I will do my best to list everything I know.
Feel free to surf the web as well. Most of the local towns have event calendars you can find online.
Special winter monthly rentals available (rate does not include utilities for stay exceeding 30 days.) Please be aware, that there are no fences. The neighbor has two labs that are very friendly and may come over to greet you. We have two small dogs as well that also like to say hi on occasion.
FYI, the school zone has camera 24/7, so watch your speed.


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Property Type

  • House
  • 1500 sq. ft.

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals


  • Events Allowed
  • Long-Term Renters Welcome
  • Minimum Age Limit For Renters:

    At least 1 person 25 yrs old....moreless

  • Children Welcome:

    For safety reasons, if you have small children, please be sure to bring life vests. We do not supply children life vests. Property is at the waters edge....moreless

  • Non Smoking Only:

    You are welcome to smoke outside provided the smoke does not enter the house....moreless

  • Pets Considered:

    $100+ extra security deposit for ea....moreless

Bedrooms: 2 Bedrooms, Sleeps 6, Beds for 6

  • Bedroom 1: 1 queen


  • Bedroom 2: 1 queen


  • Den: 1 sleep sofa /futon

    Queen size...moreless

  • Queen size Beds (2) Both bedrooms have queen beds, NO CRIB but, pac-n-play may be available with advance notice( no guarantee), Newly renovated family room with queen sleeper sofa....moreless

Bathrooms: 1 Bathroom, 1 Half Bathroom

  • Bathroom 1: toilet, combination tub/shower

    completely renovated in 2014 (extra wide tub)...moreless

  • Bathroom 1: toilet

    completely renovated 2014...moreless

  • Both bathrooms feature ceramic tile and furniture w/marble tops. Full bath has ceramic enclosure and an extra wide tub for extra room & comfort....moreless

Other Amenities

  • This home has been newly renovated to feature more amenities and more appeal. The family room features recessed lighting, a wet bar with wine frig, fireplace, new hardwood flooring. The kitchen has an open floor plan that features a full dining area as well as a breakfast bar, all new cabinetry and tile flooring, recessed lighting. A sliding glass door has been installed to the trex deck. Both bathrooms have been renovated in 2014. The front has been expanded for a more comfortable entrance. There is a horseshoe pit on the side of the house...moreless


  • DVD Player
  • Television:

    One in the family room & one in the living room...moreless

  • Video Library:

    There are some movies available for your pleasure, We have some Disney & pixar available upon request....moreless


  • Away From It All
  • Family
  • Historic
  • Romantic


  • Churches
  • Cinemas
  • Festivals
  • Health/Beauty Spa
  • Library
  • Live Theater
  • Marina
  • Museums
  • Playground
  • Recreation Center
  • Restaurants
  • Winery Tours

Local Services & Businesses

  • ATM/Bank
  • Fitness Center
  • Groceries
  • Hospital
  • Laundromat

Leisure Activities

  • Bird Watching
  • Boating
  • Horseback Riding
  • Horseshoes
  • Paddle Boating
  • Scenic Drives
  • Shopping
  • Sight Seeing
  • Walking
  • Wildlife Viewing

Location Type

  • Waterfront:

    The back is the Chester River, out front is a big o'l pond ...moreless

Sports & Adventure Activities

  • Cycling
  • Fishing
  • Freshwater Fishing
  • Golf
  • Hiking
  • Hunting
  • Hunting Small Game
  • Jet Skiing
  • Kayaking
  • Pier Fishing
  • Sailing
  • Spelunking
  • Swimming
  • Water Skiing
  • Water Tubing


  • Dining:

    dining area features a full size table (tucked leaf)with bar high chairs...moreless

  • Dining Area
  • Seating for 6 people


  • Air Conditioning
  • Clothes Dryer
  • Covered Parking
  • Fireplace:

    There is a fireplace in the family room and a fire pit outside. No wood is supplied....moreless

  • Hair Dryer
  • Heating:

    Brand new heat pump...moreless

  • Iron & Board
  • Linens Provided:

    Linens are provided but it is recommended that you bring your own. There is a $25 laundry fee if you use ours....moreless

  • Living Room:

    Spacious living room with sofa, love seat & chair...moreless

  • Parking Off Street
  • Washing Machine:

    Stack-able washer & dryer ...moreless

  • Wood Fireplace


  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher:

    brand new...moreless

  • Ice Maker
  • Kitchen:

    Brand new kitchen & eating area. That includes a breakfast bar(2013)...moreless

  • Microwave:

    brand new ...moreless

  • Oven:

    self cleaning...moreless

  • Refrigerator:

    In the family room features brand new hardwood flooring as well as a wet bar equipped with wine frig.(2013)...moreless

  • Stove:

    brand new ceramic top electric stove...moreless

  • Toaster


  • Bicycles:

    available upon advance request. Please note these are fold up bikes that were used traveling on a boat. No guarantee they function properly....moreless

  • Deck / Patio:

    Patio set with 6 chairs w/ cushions and umbrella...moreless

  • Kayak / Canoe:

    2 available. Also paddle boat & 2 boards. Used between 2 houses....moreless

  • Lawn / Garden:

    lawn chairs...moreless

  • Outdoor Grill:

    We try to keep an eye, but propane is not guaranteed to be filled. Fire pit for those cool evenings. No wood is supplied....moreless

  • Water Sports Gear:

    adult life preservers supplied. Please bring for children. ...moreless



Write a review 4.9
from 18 traveler reviews
Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
high season
May 1 - Oct 31, 2015
2 night min stay
$2,400 $5,000
Holiday rate
Nov 1 - Jan 3, 2016
2 night min stay
$325 $350
Thu, Fri, Sat
$2,300 $4,500
winter rate
Jan 4 - Apr 3, 2016
2 night min stay
$300 $350
Fri, Sat, Sun
$2,100 $4,250
Early Spring
Apr 4 - May 1, 2016
2 night min stay
$325 $350
Fri, Sat, Sun
$2,300 $4,500
May 19 - May 22, 2016
2 night min stay
* Approximate Monthly rates, actual rate will depend on the days of the month you stay

Additional information about rental rates


  • Refundable Damage Deposit $350
  • Taxes Not included


Rates are subject to change without notice until reservation is confirmed. All Holidays require a minimum of 3 nights stay( no exceptions.) $350 SD includes $75 cleaning + $25 laundry fee that is refundable if property left in a similar condition. 2 night (3 holiday) min rate is $350.00 during 2015 high season 5/01-10/31. A 4% discount is included in all pricing for payments made with checks or MO. Please add back 4% to quote if paying w/Credit Card. Guests staying 30 or more DAYS PAY SEPARATE UTILITY.

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Last updated: 07/28/2015
Check availability
23 Available
24 Available check-in
21 Unavailable
22 Today
23 Selected dates


75 Miles
Nearest Airport
2 Miles
Nearest Barpub
10 Miles
Nearest Motorway
2 Miles
Nearest Restaurant
15 Miles
Nearest Beach
Rock Hall

Car: Necessary

There is always something to do locally. If Chestertown isn't featuring an event, The next towns over are. There is a community board when you enter town that gives you details about up coming events. There is first Friday every month (local venders put out munchies and some serve beer & wine. There is the Saturday Farmer's market in the center of town. Some of the biggest events are Tea Party ( Memorial weekend), 3rd & 4th of July features Waterman's day(Rock Hall), parades, & fireworks in Chestertown, Rock Hall, & Great Oak. Friday nights usually feature musicians in the center of town(in season). Along with plenty of restaurant choices, there is a local theatre(center of town,) a movie theater in one of the 2 shopping centers and a bowling alley(featuring duck pin)just a short drive out of town. . Most of the local towns have taste of the town at one time or another. Betterton days is the first Sat in Aug.every year. Rock Hall hosts a rock fish tournament June 13-15, Pirates weekend Aug 8-10, Oct 11th is Fallfest. Dover is just 40 minutes away and Annapolis is just 45 minutes. There is a small public beach area in Rock Hall, & Great Oak & a larger beach in Betterton. There are several historical sights and local shopping. Many local restaurants to choose from. Because this is the country, there are no fences around most properties. There are 2 labs that live next door to the property. Please be aware, they are very friendly and may come over & visit.


Owner info

Year Purchased: 2012

About the owner: We were introduced to the area back in 2000 and fell in love. We reside in the property next door and felt that this was a good time to invest in a retirement plan that includes this property. We are so confident in the area, that we believe that when the market improves, so will our portfolio.

Why the Owner Chose Chestertown:
It has great potential. Every year we plan to make it better & better

The Unique Benefits at this House:
This property has great views from every room in the house. I think most will enjoy the scenic environment. Just as I do right next door.

Contact us

Speaks: english

Links to more information:



  • looking up river from the dock

    looking up river from the dock

  • Front of house

    Front of house

  • river side

    river side

  • view from deck. Also fire pit to right.

    view from deck. Also fire pit to right.

  • view of living room

    view of living room

  • view of living room

    view of living room

  • 2nd bedroom

    2nd bedroom

  • view of bathroom

    view of bathroom

  • New bathroom furniture

    New bathroom furniture

  • view of family room

    view of family room

  • view of kitchen from dinette

    view of kitchen from dinette

  • view of kitchen

    view of kitchen

  • looking down river from the dock

    looking down river from the dock

  • back of house showing new trex deck & patio set

    back of house showing new trex deck & patio set

  • view from dock.

    view from dock.

  • view from the living room bay window over looking the pond

    view from the living room bay window over looking the pond

  • view of living room

    view of living room

  • main bedroom

    main bedroom

  • view of river from bedroom #2

    view of river from bedroom #2

  • view of bathroom

    view of bathroom

  • powder room

    powder room

  • view of wet bar

    view of wet bar

  • dinette


  • view of kitchen

    view of kitchen

VRBO #431733

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This listing was first published here in 2012.

Date last modified - Thursday, July 30, 2015

Minimum stay: 1-2 nights
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Member since: 2012
Speaks: english
  • Response time Within an hour
  • Response rate 100%
  • Calendar last updated 07/28/2015
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Chester River Waterfront, Magnificent Views, Dock, Beach

Chestertown #431733

2 BR  1.5 BA  Sleeps 6

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