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 Family icon
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 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:
March 14, 2018

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 Chestertown

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:
  • Check-in: 4:00 PM / Check-out: 10:00 AM
  • 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 -
(32 traveler reviews)

78% Complete
18% Complete
3% Complete
0% Complete
0% Complete
Chester River Waterfront, Magnificent Views, Dock, Beach
average rating of 4.75 based on 32 reviews

Very good experience

  • 4 of 5

Nice area, house was nice inside and great kayaks and paddleboards. The outside of the house could use a little work but not a big deal

  • Submitted: Sep 7, 2017
  • Stayed: September 2017
  • Source: HomeAway
Did you find this review helpful?
0 0

Relaxind Weekend

  • 4 of 5

We had a terrific weekend. The house was perfect and the owners where very accommodating to my family. I would recommend this place to anyone looking to unplug and slow down and just enjoy life and there family. We will be coming back.

The Johnson Family

  • Submitted: Aug 14, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

Updated inside the house

  • 4 of 5

This is a beautiful location, the inside of the house is all updated and the outside is well appointed. The water was hot (not that the owner could do anything about that), but it means you can't really do much swimming. There are three queen beds, so if you bring people that don't normally sleep together, remember it does fit 6 people, but only in shared beds. So, as there are only two bedrooms, I thought it was a little expensive. I would recommend this house and the owners, and I would come back but for two bedrooms, it's a bit expensive.

  • Submitted: Jul 31, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
1 0

The Perfect Vacation!!!

  • 5 of 5

We enjoyed a month of happy days, beautiful scenery, wildlife, in this charming home on the Chester River! The cottage more then met our expectations. Since we were "coming home" from the West Coast to visit many far flung family and friends, we wanted a place of our "own" so that our guests could come to us and share a bit of Eastern Shore charm and catch up with each other. The deck was a perfect place to visit, share a cocktail or two and reminisce the "old days" with our friends. The cottage is charming, nicely furnished, very clean and the washer/dryer is a great addition. There was plenty of room for everyone to gather - whether in the kitchen, dining area or one of the two living areas -- just perfect!!! Many of our visitors are looking forward to a return visit and have recommended the cottage to some other friends. An unexpected gift to us was the beautiful double rainbow that actually came to an end at the end of the road!l. Thank you Dianna and Russ for being the best "neighbors" and owners, but, most of all for making this little piece of heaven available to us --- you rock! Dreaming of our next trip!

  • Submitted: Jul 22, 2017
  • Stayed: June 2017
  • Source: VRBO, from HomeAway
Owner's Response: You guys were the perfect guests. We cannot wait to see you again.
Did you find this review helpful?
0 0
Maple Glen, PA

Great home in a great place!

  • 5 of 5

We loved staying at Russ and Dianna's home. The Chester river is always spectacular, and the the home is so nice and cozy!

  • Submitted: Jul 14, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
Owner's Response: We are so happy that your enjoyed yourselves. We strive to make your stay the best it can be and we hope to see you in the future.
Did you find this review helpful?
0 0

A Terrific Getaway Right on the Water

  • 5 of 5

A charming, well furnished home on the Chester River with easy access to the water for the furnished kayaks and paddle boards. It has a large well-equipped kitchen with a great view of the river and a very pleasant deck where we dined al fresco while watching the activities on the water. It was a terrific getaway. The owners are very helpful and accommodating.

  • Submitted: Jul 5, 2017
  • Stayed: July 2017
  • Source: HomeAway
Owner's Response: Thank you for your review. We are thrilled your enjoyed yourselves and hope to see you again in the future.
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.




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