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Chester River Waterfront, Magnificent Views, Dock, Beach

(25 Reviews)

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Last updated: 04/23/2017
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:2-3 nights
  • Sleeps:6
  • Bedrooms:2
  • Bathrooms:1.5
  • Property type:House
  • Internet:No
  • Pets considered:Yes
  • Wheel chair accessible:N/A

About the Property

1500 sq ft 2 br/1.5 ba Family room

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 decorative fireplace. The kitchen & dining area feature an open floor plan with 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 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 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. 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 2017 season
Chestertown Tea Party is every memorial day weekend, Rock fish tournaments usually early June and mid Sept
Sunday on 4th of July weekends is 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 usually the fist weekend in Aug
The second weekend in Aug is pirate's weekend in Rock Hall another great time to be had. Lots of people dress up for the event. Sultana down rigging late Oct early Nov, early Oct is Rock Hall's 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 stays 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.
Send email


Member since: 2012

Speaks: english
Response time: Within an hour
Response Rate: 100%
Calendar last updated: 04/23/2017

Property Type

  • House
  • 1500 sq. ft.

House Rules

  • Max. occupancy 6
  • 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

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals


  • Long-Term Renters Welcome

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 renovated to feature more amenities and more appeal. The family room features recessed lighting, a wet bar with wine frig, decorative fireplace, hardwood flooring. The kitchen has an open floor plan that features a full dining area as well as a breakfast bar, new cabinetry and tile flooring, recessed lighting. A sliding glass door has been installed to the trex deck. Both bathrooms have been renovated. The front has been expanded for a more comfortable entrance. ...moreless


  • Satellite / Cable:


  • 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
  • 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 decorative fireplace in the family room( not usable) but there is a fire pit outside. Wood is generally available....moreless

  • Hair Dryer
  • Heating:

    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
  • Ice Maker
  • Kitchen:

    new kitchen & eating area. That includes a breakfast bar...moreless

  • Microwave
  • Oven:

    self cleaning...moreless

  • Refrigerator:

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

  • Stove:

    new ceramic top electric stove...moreless

  • Toaster


  • 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. ...moreless

  • Water Sports Gear:

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



Write a review 4.8
from 25 traveler reviews
Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
Early Spring
Apr 1 - May 18, 2017
2 night min stay
$325 $350
Fri, Sat, Sun
$2,000 $3,750
high season
May 19 - Nov 5, 2017
2 night min stay
$2,200 $5,000
Holiday rate
Nov 6 - Jan 1, 2018
3 night min stay
$325 $350
Thu, Fri, Sat
$2,000 $4,000
Winter Season
Jan 2 - Apr 1, 2018
2 night min stay
$300 $350
Fri, Sat, Sun
$1,800 $3,750
My Standard Rate
2 night min stay
$2,200 $5,000
* Approximate Monthly rates, actual rate will depend on the days of the month you stay

Additional information about rental rates


  • Refundable Damage Deposit $350


Rates are subject to change without notice until reservation is confirmed. 2 night minimum/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 & you use your own linens. Guests staying 30+ DAYS PAY SEPARATE UTILITY. ANY FEES CHARGED(credit/paypal) WILL BE ASSUMED BY THE GUEST AND WILL BE TAKEN FROM SECURITY DEPOSIT AFTER CHECK OUT.

Owner's cancellation policy:

Cancelled bookings will not receive a refund.

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Last updated: 04/23/2017
Check availability
23 Available
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, MD, USA:
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
Response time: Within an hour
Response Rate: 100%
Calendar last updated: 04/23/2017

Send email

Links to more information:



  • 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 of living room

    view of living room

  • main bedroom

    main bedroom

  • view of bathroom

    view of bathroom

  • New bathroom furniture

    New bathroom furniture

  • view of family room

    view of family room

  • dinette


  • looking up river from the dock

    looking up river from the dock

  • view of wet bar

    view of wet bar

  • view of kitchen

    view of kitchen

  • Front of house

    Front of house

  • view from deck. Also fire pit to right.

    view from deck. Also fire pit to right.

  • 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

  • view of living room

    view of living room

  • view of bathroom

    view of bathroom

  • powder room

    powder room

  • view of kitchen from dinette

    view of kitchen from dinette

  • river side

    river side

  • 2nd bedroom

    2nd bedroom

  • view of river from bedroom #2

    view of river from bedroom #2

  • view of kitchen

    view of kitchen

VRBO #431733

This listing was first published here in 2012.

Date last modified - Tuesday, April 25, 2017

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