Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled
Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Chester River Waterfront, Magnificent Views, Dock, Beach

Bedrooms 2
Half Baths1
Space 1,500 sq. ft.
Property type house
Minimum Stay 2 - 3 nights


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.

More Details

Dianna or Russell
Member since: 2012
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
June 23, 2017

About Dianna or Russell

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.

Dianna or Russell purchased this house in 2012

Why Dianna or Russell chose Eastern Shore

It has great potential. Every year we plan to make it better & better

What makes this house unique

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.


Chestertown House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 1500 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
  • Covered Parking
  • Fireplace ...
  • Hair Dryer
  • Heating ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking Off Street
  • Washing Machine ...
  • Wood Fireplace
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen ...
  • Microwave
  • Oven ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • 1 Half Bath
  • Bathroom 1 - toilet , combination tub/shower , completely renovated in 2014 (extra wide tub)
    Bathroom 1 - toilet , completely renovated 2014
  • Both bathrooms feature ceramic tile and furniture w/marble tops. Full bath has ceramic enclosure and an extra wide tub for extra room & comfort.
  • 2 Bedrooms, Sleeps 6
  • Bedroom 1 - 1 queen
    Bedroom 2 - 1 queen
    Den - 1 sleep sofa /futon , Queen size
  • 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.
  • DVD Player
  • Games ...
  • Satellite / Cable ...
  • Television ...
  • Video Library ...
  • Deck / Patio ...
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Water Sports Gear ...
  • 6 garden chairs
  • 4 beach chairs
  • Long-term Renters Welcome
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
  • winery tours
Leisure Activities:
  • bird watching
  • boating
  • horseback riding
  • horseshoes
  • paddle boating
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
Sports & Adventure Activities:
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • hiking
  • hunting
  • jet skiing
  • kayaking
  • pier fishing
  • sailing
  • spelunking
  • swimming
  • water skiing
  • water tubing
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.


Wonderful! 4.8/5 -
(26 traveler reviews)

Chester River Waterfront, Magnificent Views, Dock, Beach
average rating of 4.8076925 based on 26 reviews

Quaint, beautiful waterfront

  • 5 of 5

Dianna and Russell were very nice, the property was as described, and it was very nice to sit outside and enjoy the river. I would recommend and would stay again if I'm in the area.

  • Submitted: Jun 7, 2017
  • Stayed: Jun 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

Beautiful Views!

  • 5 of 5

We stayed at this little house for a sibling reunion to remember our mom. It was an emotional trip as we don't see each other often and we hadn't been back to Chestertown since our grandparents passed away. They were long time residents of Chestertown, and we grew up spending summers and long weekends there.

We chose this place for it's location and similarities to our grandparents' location. The house was clean and tidy, and it was perfect for our purposes. Very close to town and the views were amazing. We made good use of hanging out on the dock and around the firepit. My brother was able to bring his dogs and they enjoyed the outdoors too. The house was nicely decorated and updated. We thought it was adorable and will definitely consider coming back again another time. We had a lovely stay.

Communication with Dianna was great and she was very accommodating. I saw the review from a previous guest regarding ants. They came around when we were there too, but this is the time of year when you see ants. If you have a problem with bugs or spiders, the woods may not be for you. The owner let us know about the possibility of ants and that they'd sprayed and/or used traps. She didn't see any before we arrived and neither did we. Once we had food in the house, we started seeing them, but the owner left us ant baits. We just made sure not to leave food out and it really wasn't a big issue.

  • Submitted: Nov 7, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for your review. We are very happy that our little place lived up to your expectations. We are also glad that you were able to enjoy treasured memories. We do hope to see you again in the future.
Did you find this review helpful?
0 0

updates inside - outside needs work

  • 3 of 5

The kitchen in this house is well stocked with about anything you would need. The kitchen is updated & overlooks the river. Very pretty! Unfortunately there were ants on counters, stove & even the table. We needed to keep all food in the fridge. The house was clean & neat inside. The sofa bed was not usable - very very uncomfortable. the other two beds dipped in the center. It lists bikes as one of the items for renters use, but they sat off to the side very dirty and with flat tires. The outside of the house is missing pieces of siding, & soffits. I think this house is a work in progress. The dock & view were very nice. The owners live next door & their dog comes over and leaves a deposit in the lawn each morning. ugh!

  • Submitted: Oct 10, 2016
  • Stayed: Oct 2016
  • Source: HomeAway
Owner's Response: We have the unique distinction of not only being an active landlord, but we also reside next door. This benefits our guests in the way that if any issues should come up, we can address them immediately. Unfortunately, we were not notified of any issues. The property was last updated when it was built, so we have been updating the property in the off seasons. That way, we do not to disturb our guests. So yes, this is a work in progress. We update and modify what we feel would best serve our guests as a whole and naturally the outside of the house is the last thing that we will take care of. The bikes are outside and not used by many guests so, we were unaware of the flat tires. As far as the dogs go, there are no fences between properties. I do have 2 dogs (9 lbs & 4 lbs) that are generally supervised when outside, but occasionally do stray. If we notice this, we go get them and bring them back. If I should see them have a bm, I will pick it up. I have on occasion had issue with the neighbor’s dog, but I try to keep on top of them to clean up. This can be difficult at times, and I apologize for any inconvenience.
Did you find this review helpful?
0 0

Great Cottage

  • 4 of 5

We really enjoyed our stay. Worked really well for us. It is clean and roomy. The dock and the beach were great. My dog especially enjoyed the trip. He was in the water the whole time. Close to town. The owners were very nice as well.

  • Submitted: Sep 14, 2016
  • Stayed: Sep 2016
  • Source: VRBO, from HomeAway
Owner's Response: We are so happy that you enjoyed your visit. I am sorry that we were lacking in some way to prevent a 5 star rating. We strive to make your stay the best possible. We certainly hope to see you again in the future.Thank you for choosing to stay with us during your visit to the Chestertown area.
Did you find this review helpful?
0 0

Wonderful riverfront escape

  • 5 of 5

This was a great place for a weekend getaway. The location and house were exactly as pictured, although there was a lot more beachfront than we expected which was great. Dianna was super easy to communicate with and very flexible. She even took the trouble to mail back things we had left in the house. It's a great location and close enough to historic Chestertown and grocery stores, etc., but when you are at the house you feel like you are really getting away from the grind. We loved sitting on the dock watching bald eagles and ospreys and had a very peaceful weekend.

  • Submitted: Aug 5, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
Did you find this review helpful?
0 0
Garnet Valley, PA

Great house, hosts, and location! Thank you!

  • 5 of 5

I rented this house back in October 2015 for a girls' weekend and recently returned with my family. The location and accommodations were perfect for us… right on the water with a private dock and boat ramp. We brought our jet ski, but you could easily bring a large boat. The house is completely remodeled was very comfortable for 6 adults. We took advantage of the complementary kayaks, paddle boards, paddleboat, fire pit, and grill. One of the most important features for us was that the house is pet friendly (with the owner's approval), which is often difficult to find… our dog had a great time swimming from the beach! Dianna and Russell were great and went out of their way to make sure we had everything we needed. We will be back!

  • Submitted: Jul 18, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
Did you find this review helpful?
0 0


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. 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.


Rates & Availability

Chestertown House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
high season
May 19 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 $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

  • Canceled bookings will not receive a refund
Contact Owner

You might like these similar properties