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Book Online or call HomeAway Booking Assistance 888-640-7927

WATERFRONT 3 BR/1 ba country cottage w/ gameroomdeep water,dock, 2 mi from town

Bedrooms 3
Space 1,200 sq ft
Property type cottage
Minimum Stay 2 nights


About the property

A private, tranquil, waterfront location 1200 sq ft house w/ 3 acres

You can rent this adorable cottage that has the best of every world. This property is located just 2 short miles from historic Chestertown but, situated in a country setting on a deep creek (Morgan creek) with over 2 acres of privacy. The house is 1200 sq. ft. that includes a living room, 1 bathroom, 3 bedrooms, large kitchen with a breakfast bar and full dinning area, stacked washer & dryer. The house has hardwood flooring and newer windows. A swing in the big Maple tree out back for two. A fire pit installed out back for those chilly nights or making smoors. The shed out back has been converted into a game room equipped with ping pong table( was donated to the cause) cards & various board games. There is a 40’ dock with a 10 X 20’ “L” head that is great for boating, cat fishing(really big ones in there,) swimming, or just plain hangin’ out with a cool drink. The water is approximately 19’ at the end of the dock. Children & dogs are welcome. 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 first weekend in Aug

The second weekend in Aug is pirates 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.

FYI, the school zone has camera 24/7, so watch your speed.

More Details

Dianna or Russell
Member since: 2012
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
September 21, 2018

About Dianna or Russell

My husband and I were first introduced to the eastern shore by very good friends in 2000. We fell in love and purchased a boat, then a bigger boat, then a house, then a bigger house. We are there almost every weekend of the year. The house we live in now is just around the corner from this property. We have been married for 30+ years, have 2 girls, 2 son-in-laws and 1 grandchild so far. Both of us grew up in Delaware county, PA

Dianna or Russell purchased this cottage in 2005

Why Dianna or Russell chose Chestertown

This was the first home we bought on the eastern shore and I just cannot part with it. It is the perfect place for privacy, serenity, & relaxation. There are so many things to do between Chestertown & Rock Hall. There is always a festival or craft fair, waterman's days, Pirate's weekend(picture), Tea party, the best fireworks & some of the best restaurants in the area. We have had annual tenants for the last 4 years but, this year we wanted to try weekly rentals so that our children could have a place to stay occasionally. I know that you will fall in love with it just as we did.

What makes this cottage unique

I remember how we used to go down to the dock with some snacks and a cool drink, watch the sun go down, watch all the wild life( ospry's ,eagles etc.), and feel completely alone with nature. Only during the winter months can you even see the property across the marsh. On any clear night, there are millions of stars in the sky. You can even see the milky way on occasion. The Legion occasionally has events but they are few and far between and always over by 10pm. You can have camp fires, bar-b-ques, and sit in a swing and melt the everyday stress away. There is large catfish in the creek. Crabs make their way up the creek around mid Sept. The water is nice and deep at the end of the dock so, your feet never touch the muddy bottom. Plenty of water fowl all year long.

Guestbook comments from the owner

During our the chestertown house owned by Mrs. Dianna Frymiare was a great stay. The house was very nice. We all enjoyed our stay so much. Looking forward to going back. The children loved it!
Aug 2012
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Chestertown Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
Floor Area:
  • 1200 sq ft
House Rules:
  • Max. occupancy: 6
  • Minimum Age Limit for Renters ...
  • pets considered ...
  • children welcome
  • non smoking only ...
Location Type:
  • Waterfront ...
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace
  • Hair Dryer
  • Heating ...
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Parking
  • Parking Off Street
  • Towels Provided ...
  • Washing Machine
  • Wireless Internet
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven ...
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • seating for 8 people
  • 1 Bathroom
  • Bathroom 1 -
  • full size tub & shower
  • 3 Bedrooms, Sleeps 6
  • Bedroom 1 - 1 queen
    Bedroom 2 - 1 queen
    Bedroom 3 - 1 bunk bed , one full/one twin
  • Queen size Beds (2) 2 queens, NO CRIB but, pac-n-play possibly available with advance notice (no guarantee for availability so request early), Bunk Beds (1) There is a full & a twin
  • CD Player
  • DVD Player
  • Game Room ...
  • Games ...
  • Ping Pong Table
  • Satellite / Cable ...
  • Stereo
  • Television
  • Video Library ...
  • Deck / Patio ...
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Outdoor Grill
  • 6 garden chairs
  • Long-term Renters Welcome
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • playground
  • recreation center
  • restaurants
  • winery tours
Leisure Activities:
  • antiquing
  • bird watching
  • boating
  • eco tourism
  • horseback riding
  • scenic drives
  • shopping
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
Sports & Adventure Activities:
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • hunting
  • jet skiing
  • kayaking
  • pier fishing
  • sailing
  • spelunking
  • swimming
  • water skiing
  • water tubing
40' dock with 10 x 20 'L' head. Creek is 19 ' deep at end of dock. Great for fishing, swimming, boating, & relaxing. Bring a float and tie off at the dock. A new fire pit was installed fall of 2013 & game room ready in the outbuilding for spring 2014.


Wonderful! 4.8/5 -
(29 traveler reviews)

86% Complete
10% Complete
3% Complete
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WATERFRONT 3 BR/1 ba country cottage w/ gameroomdeep water,dock, 2 mi from town
average rating of 4.827586 based on 30 reviews

Perfect getaway! Cozy cottage in a great location

  • 5 of 5

We had an amazing time kayaking & swimming in the creek then bike riding to Chestertown. House was very clean with all the needed amenities. Perfect for a family of four.

  • Submitted: May 28, 2018
  • Stayed: May 2018
  • Source: VRBO, from HomeAway
Owner's Response: We are so happy you enjoyed yourselves and we hope to see you again in the future.
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Great for a family

  • 4 of 5

We had a great time. The house was very clean and comfortable. The grandkids had a lot of room inside and out. Already want to return. Thank you for a great vacation spot.

  • Submitted: Aug 6, 2018
  • Stayed: July 2018
  • Source: VRBO, from HomeAway
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Good size home in the Chesapeake

  • 5 of 5

The house was the perfect size for our party. We enjoyed our stay and would recommend it to anyone looking for a nice weekend in the Chesapeake!

  • Submitted: Jun 4, 2018
  • Stayed: May 2018
  • Source: VRBO, from HomeAway
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Cozy Country Cottage

  • 5 of 5

We had a top notch family weekend getaway, complete with Harry Potter experiences! The kids enjoyed catching a variety of fish (catfish, rock, eel) and a painted turtle! I got to sit back, relax, and read a book while they were fishing! And we all enjoyed the fire pit and smores! GREAT WEEKEND!!!

  • Submitted: Oct 11, 2017
  • Stayed: October 2017
  • Source: HomeAway
Owner's Response: We loved having you as our guest and we hope that you will stay with us the next time you are in town. Next year's HPFestival promises to be bigger and better. Russ & Dianna
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  • 5 of 5

I stayed here with my family for a last minute weekend getaway. It was very homey and clean. We enjoyed the backyard and had some fun with the outdoor bench and swing. Being on the water made it that much better, so we took advantage and went on a nice little kayaking trip. We (for my family) lucked out with getting decent thunderstorms each night. Was beautiful scenery in this peaceful and quiet location. Still close to town! Would definitely book again! Very kind and accommodating! :)

  • Submitted: Aug 31, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Great Place

  • 5 of 5

We have stayed here several times over the past couple of years, as a short family vacation and have enjoyed our stay and would highly recommend to anyone looking to explore the Chester River.

  • Submitted: Aug 18, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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Nearest Airport
75 Miles
Nearest Barpub
2 Miles
Nearest Motorway
10 Miles
Nearest Restaurant
2 Miles
Nearest Beach
15 Miles
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(Fountain Park.) Also on most Saturdays evenings in season, musicians play in Fountain Park. 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. 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. Please search the internet and the local commerce for lists of upcoming events.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $125
Refundable Damage Deposit $250

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.) $250 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

100% refund if canceled at least 90 days before arrival date.

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