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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 - 3 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
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
July 25, 2017

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 Eastern Shore

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 Off Street
  • Towels Provided ...
  • Washing Machine
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven ...
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • seating for 6 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 -
(23 traveler reviews)

WATERFRONT 3 BR/1 ba country cottage w/ gameroomdeep water,dock, 2 mi from town
average rating of 4.826087 based on 24 reviews
Glen Mills, PA

comfortable, peaceful respite

  • 5 of 5

Property was perfect little oasis for our July 4th retreat. Plenty of room and everything updated. Owners were very responsive. Would definitely return.

  • Submitted: Jul 10, 2017
  • Stayed: Jun 2017
  • Source: VRBO, from HomeAway
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Lazy day by the creek

  • 4 of 5

This was a perfect location for us, near family and yet our own mini get away. We had dinner in Chestertown, spent a day on the dock by the creek, and had family time. The house was very comfortable and our greyhound had plenty of areas to take on a walk.

  • Submitted: Jul 28, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
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September weekend

  • 5 of 5

Stayed here over a weekend this September. Perfect location, quiet street, large yard with firepit and dock, took advantage of it all. House was clean, had everything needed, owner was nice and very accommodating. recommended highly

  • Submitted: Sep 23, 2015
  • Stayed: Sep 2015
  • Source: VRBO, from HomeAway
Owner's Response: We loved having you guys again this year and we look forward to seeing you next time you are in town.
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Media, PA, USA

Great getaway!

  • 5 of 5

This house was a wonderful place to stay with my family and I! We enjoyed the dock and kayaks. The swings in the backyard were an excellent place to enjoy a cup of coffee in the morning! The peaceful atmosphere made for an incredibly relaxing long weekend. The fire pit made for delicious s'mores and good times. Also, great games of ping pong occurred by the kids. Lastly, the shaded areas throughout the backyard was a great way to beat the heat! It was an amazing weekend that we all enjoyed and can't wait to return next year.

  • Submitted: Aug 3, 2015
  • Stayed: Jul 2015
  • Source: VRBO, from HomeAway
Owner's Response: You have been the perfect guests, this year and years past. We look forward to you & your family again in the future .
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Washington, District of Columbia

Great place to unwind!

  • 5 of 5

We stayed in this cute and comfortable cottage over the July 4 weekend. There were five adults and one dog. We had plenty of both indoor and outdoor space to relax. I especially enjoyed the swing and sitting out by the water. If you want a quiet country getaway, this place is for you. We took advantage of the kayaks Dianna left us and enjoyed bike rides on traffic-free country roads (the main road with more traffic has a huge shoulder to ride on - very safe). We enjoyed First Friday in Chestertown, with live music, free lemonade and popcorn, and a nice fireworks display in Rock Hall (about 20 mins away). The men in our group also rented a small boat at a Rock Hall for a morning fishing trip. All in all, an enjoyable weekend, and Dianna was very responsive and just a phone call away.

  • Submitted: Jul 17, 2015
  • Stayed: Jul 2015
  • Source: VRBO, from HomeAway
Owner's Response: We are so happy you enjoyed your stay and we hope to see you again in the future. Thank you for being the perfect guest.
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Great Family Vacation

  • 5 of 5

Went here with my family for a long weekend vacation. We had so much fun and there was something to do for everybody! We caught some fish on the pier, played table tennis, had fun on the swings, went kayaking, and had smores using the fire pit - it was just so serene and relaxing. Our dog had a lot of fun roaming around with us too! We also went into town which is not far and went to the farmer's market there for fresh veggies! Also, Dianna was just so sweet and helpful throughout the entire process. She was incredibly responsive to our emails and questions and met us at the house to show us around. Would absolutely recommend this place for a nice relaxing vacation on the eastern shore!

  • Submitted: Jul 17, 2015
  • Stayed: Jul 2015
  • Source: VRBO, from HomeAway
Owner's Response: We are thrilled you got the most out of the property and enjoyed yourselves. we hope to see you again in the future. You were the perfect guests.
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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

Chestertown Cottage Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
High Season
May 22 2017 - Nov 5 2017
2 night minimum stay
Holiday rate
Nov 6 2017 - Jan 1 2018
3 night minimum stay
Winter Season
Jan 2 2018 - Apr 1 2018
2 night minimum stay
My Standard Rate
2 night minimum stay

Additional information about rental rates

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.
Contact Owner

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