Title: Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town - Latest Reviews, Deals & Photos 2025 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town Riverfront vacation home with kitchen and balcony ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/39c19e25.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/1680c746.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/37d3c420.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/4b182ec5.jpg?impolicy=resizecrop&rw=297&ra=fit) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/6557d1f4.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location You can look forward to free breakfast, a firepit, and laundry facilities at Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town. Adventurous travelers may like the kayaking at this vacation home. Stay connected with free in-room WiFi. 9.8 Exceptional ### Entire home 3 bedrooms3 bathroomsSleeps 62100 sq ft ## Popular amenities - Dryer - Washer - Fireplace - Parking available - Breakfast included - Barbecue grill ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town Chester River Dreams, offers spectacular views of the Chester River from the Family room, 2 bedrooms, Kitchen, & Dining room, Deck, 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 3 large bedrooms (3 queen beds + 2 twins.) Each bedroom has smart TVs. Two have views of the river & the other has views of the large pond out front. The family room features a queen sleeper sofa with air mattress & has a view of the river. The family room features hardwood flooring, wet bar w/wine frig, recessed lighting, smart TV, 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 sliding glass doors from the dining area that will go out to a large deck that has a cushion patio set & umbrella. There is a laundry area that includes a stacked washer & dryer. All bathrooms have been 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. Bar-B-Que grill, (propane) as well as plenty of Adirondack chairs. Kayaks & paddle boat & boards are available (pls note, although there are 4 adults life vests, we do not supply children's life vests. Although, we have young grandchildren & as long as they are not in use, feel free to borrow.) There is also a fire pit for those cool nights or to just hang out and make smoors. High speed internet added in 2021 NEW for 2022! The interior and exterior have been freshly painted. New siding and new living room furniture, new patio cushions, 6 smart tv's & ceiling fans. New for 2025! upstairs bedroom with walk in closet and private bath. HUNTERS WELCOME!! For any of you NASCAR fans, we are situated only 40 minutes from Dover Track. We are also 25 minutes from Rock Hall & 45 minutes from Annapolis. 35 minutes from premium outlets in Queenstown. \*\* Some dates to consider for fun filled family weeks. 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. This whole area is loaded with festivals. Here's a few more. 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. In Chestertown, Sultana down rigging late Oct early Nov, early Dec is Dicken's weekend & 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. 3rd Thurs 6-8 pm is cars on high April thru Oct. 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. Neighbor has two dogs that are very friendly and may come over to greet you. FYI, the school zone has camera 24/7, so watch your speed. ## Property amenities ### Beach - Beach nearby - Beach towels ### Internet - Available in the house: Free WiFi ### Parking and transportation - Car required - Parking on site ### Kitchen - Blender - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Ice maker - Kitchen island - Microwave - Oven - Paper towels - Refrigerator - Spices - Stovetop - Toaster ### Dining - Free breakfast available - Dining table - Wet bar ### Bedrooms - 3 bedrooms - Bedsheets provided - Sofa bed ### Bathroom - 2.5 bathrooms - Bathtub or shower - Hair dryer - Shampoo - Shower - Soap - Toilet paper - Towels provided ### Living spaces - Dining table - Fireplace - Living room ### Entertainment - DVD player - Games - Smart TV with cable/satellite channels - Video library ### Outdoor areas - Barbecue grill - Dock - Firepit - Outdoor furniture - Patio ### Laundry - Laundry facilities - Washer/dryer ### Work spaces - Desk - Desk chair ### Comfort - Air conditioning - Ceiling fan - Heating ### Pets - Pet friendly - 2 pets total (up to 50 lbs per pet) ### Suitability/Accessibility - Tile flooring in public areas - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - Near a health/beauty spa - Near a hospital - Near an outlet shopping mall - Near the marina - On a river - On the waterfront ### Things to do - Kayak - Water sports equipment - Basketball nearby - Birdwatching nearby - Cycling nearby - Fishing nearby - Golfing nearby - Hiking/biking trails nearby - Hunting nearby - Jet skiing nearby - Kayaking nearby - Motor boating nearby - Sailing nearby - Spelunking nearby - Swimming nearby - Water skiing nearby - Water tubing nearby - Wildlife walks nearby - Winery tours nearby ### Safety features - Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector) - Smoke detector (host has indicated there is a smoke detector on the property) - Fire extinguisher - Deadbolt lock ### General - At least 80% lighting from LEDs - Recycling - Unit size: 2,100 square feet - Water-efficient showers ## Similar properties ![Exterior](https://images.trvl-media.com/lodging/35000000/34530000/34520600/34520502/fed476c4.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown Worton - Kitchen - Washer - Dryer - Pet-friendly 9.8 Exceptional 94 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-13&endDate=2025-11-14&selected=34520502&PinnedHotelID=34520502&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/118000000/117470000/117463700/117463692/4d322b5b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Eastern shore beachfront cottage with stunning sunset views! 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Do not use bath towels for beach or pets. No wet pets in the house, No pets on the furniture. Do not use bedding 4 pets Smoking is permitted outside the house. Take care not to let smoke inside. Extra fees may be charged if cigarette/cigar odors are inside the house. Minimum of 2 night are required EXCEPT for holidays. Minimum of 3 nights for ALL holidays. NO SATURDAY check- in for 7 days or longer. ### Pets Pets allowed Service animals are welcome, and are exempt from fees 2 total (up to 50 lbs per pet) Restrictions apply; for more information contact the property at the number on the booking confirmation Note from host: 4 pets weighting over 60lbs, please contact owner. ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed Onsite parties or group events are strictly prohibited Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher and a deadbolt lock This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### We should mention A car is required for transportation to and from this property ### Property is also known as Chester River Waterfront Magnificent Views Dock Beach House Chester River Waterfront Magnificent Views Dock Beach River Waterfront Magnificent Views Dock Beach River Waterfront Magnificent Chester River Waterfront Magnificent Views Dock Beach ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C39.22257%2C-76.04087&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=8tWc5xntbWa0ct0vzkXJeTVYobk=) Chestertown, MD #### What's nearby - Chestertown Dog Park - 6 min drive - 4.2 km - Washington College - 8 min drive - 6.3 km - Historical Society of Kent County Maryland - 8 min drive - 7.0 km - River Arts Chestertown - 9 min drive - 7.3 km - Rolphs Wharf Marina - 20 min drive - 16.0 km #### Getting around - Baltimore, MD (MTN-Martin State) - 110 min drive #### Restaurants - ‪Royal Farms - ‬7 min drive - ‪McDonald's - ‬7 min drive - ‪Royal Farms - ‬10 min drive - ‪Dunkin - ‬6 min drive - ‪Procolino's - ‬6 min drive ## Frequently asked questions ### Is Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town pet-friendly? > Yes, this property allows pets (limit 2 total) with a maximum weight of up to 50 lbs per pet. Some restrictions may apply, so please contact the property for more details. ### What time is check-in at Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town? > Check-in begins at 4:00 PM. ### What time is check-out at Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town? > Check-out is at 10:00 AM. ### Where is Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town located? > This family-friendly Chestertown vacation home is located on the waterfront, within 3 mi (5 km) of Chestertown Dog Park and Rolling Road Park. Chestertown Historic District and Wilmer Park are also within 6 mi (10 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town Reviews 9.8 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) ### 10 Cleanliness ### 10 Location ### 10 Property conditions & facilities 10 - Excellent 77 8 - Good 7 6 - Okay 1 4 - Poor 0 2 - Terrible 0 ### 10/10 Excellent #### steven s. Jul 25, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Everything we needed was there. Owners next sore are super nice and hrphful. ##### steven s. Stayed 3 nights in Jul 2025 ### 10/10 Excellent #### Stephen H. Jun 7, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy We had a wonderful weekend. Thank you! ##### Stephen H. Stayed 3 nights in May 2025 ### 10/10 Excellent #### Lauriann S. Jul 17, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great Location for a Getaway Perfectly situated for exploration of the area. You can explore the city of Chestertown or venture further afield to Annapolis. Perhaps you just want to rest and decompress? Take your coffee to the dock and watch the water. The house is charming and the kitchen is equipped for the best of meals. In a nutshell- this house is a gem! Definitely would recommend. ##### Lauriann S. Stayed 2 nights in Jul 2025 ### 10/10 Excellent #### Bob R. Jun 19, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great location Loved the location next to the river. Spent a lot of time on the dock and in the yard. Proximity to Chestertown a real plus too. Great hosts! ##### Bob R. Stayed 2 nights in Jun 2024 ### 10/10 Excellent #### Sun P. Nov 8, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great location! Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts. ##### Sun P. Stayed 3 nights in Nov 2024 ### 10/10 Excellent #### Lisa V. Aug 17, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Weekend away Excellent hosts. Everything we needed. Beautiful views! ##### Lisa V. Stayed 2 nights in Aug 2022 ### 10/10 Excellent #### Sarah R. Jun 23, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect River Stay House was even better than the photos showed. We spent evenings out on the dock watvhing the river and beautiful views. The hosts thought of every detail for a perfect stay. ##### Sarah R. Stayed 2 nights in Jun 2024 ### 10/10 Excellent #### John U. Nov 6, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Riparian Tranquility Beautiful views of the river, tranquil neighborhood, great house. Perfect place to decompress and get away for a week. ##### John U. Stayed 7 nights in Oct 2022 This review was submitted before 2018 and has not been verified. ### 10/10 Excellent #### Laura D. Oct 13, 2014 #### Girls weekend Great, relaxing vacation. House is clean and beautiful with great backyard area. Owners are right next door and great hosts. Very quiet area with some good restaurants, a few bars, and a winery nearby. ##### Laura D. ### 10/10 Excellent #### Allie P. Sep 17, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great home Home was very clean and neat. We enjoyed the snacks, and little touches. ##### Allie P. Stayed 2 nights in Sep 2023 ### 10/10 Excellent #### Verified traveller Jul 25, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Wonderful location! My sister and I spent a weekend away at this property. It was very clean, extremely quiet, and the views incomparable. We spent the bulk of our time relaxing in the Adirondack chairs on the dock. With a constant breeze off the water, it was perfect! ##### Verified traveller Stayed 2 nights in Jul 2021 ### 10/10 Excellent #### Michael B., Arlington Jun 1, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great home on the water! This was a wonderful property right on the water with absolutely stunning views. The host was extremely responsive and a pleasure to interact with. I highly recommend this home to anyone looking for a relaxing stay on the water! ##### Michael B. Stayed 3 nights in May 2021 ### 10/10 Excellent #### Amber U. Oct 9, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Family weekend at Washington College We had a great stay and the property is well maintained. They had a lot of extras for our convenience such as toothbrushes, snacks, and more. The dock and view was beautiful and relaxing. We plan to come back soon! ##### Amber U. Stayed 2 nights in Oct 2023 ### 10/10 Excellent #### Catherine M. Sep 2, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stay! Very nice owner. Super helpful and dealt with our leaving stuff! Mailed the oops we left that so nicely. Cheers! ##### Catherine M. Stayed 7 nights in Jul 2023 ### 10/10 Excellent #### Elamurugan S. Aug 20, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Chestertown Vacation The property was awesome. We kayaked, kids enjoyed paddle boats, and relaxing by the water. The owners were excellent hosts. Chestertown farm market on saturday(s) is a must see. Dog friendly township. Will go back next summer. ##### Elamurugan S. Stayed 3 nights in Aug 2023 ### 10/10 Excellent #### Elsie D. Jun 24, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Wedding weekend Very clean. Beautiful view. ##### Elsie D. Stayed 2 nights in Jun 2022 This review was submitted before 2018 and has not been verified. ### 10/10 Excellent #### Morgan G. Jul 18, 2014 #### Beautiful Views!!! This house was a perfect weekend getaway for my family and our children. We loved the house which has been newly renovated and the backyard was perfect to spend our days outside on the river! The house had everything we needed and Diana (the owner) was such a big help in making us feel comfortable. We would come back here in a heartbeat! ##### Morgan G. This review was submitted before 2018 and has not been verified. ### 8/10 Good #### Tim N. Sep 14, 2016 #### Great Cottage 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. ##### Tim N. Stayed 3 nights in Sep 2016 ### 10/10 Excellent #### Patricia C., Northern Virginia Aug 8, 2019 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Waterfront fun The location and the amenities were great. We had one issue that the owner quickly responded to. Really enjoyed the paddle boards, kayaks and the outside deck. The neighbors are friendly, the house is nice and has a beautiful view. ##### Patricia C. Stayed 2 nights in Aug 2019 ### 10/10 Excellent #### James S. May 11, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Too bad for the weather! I certainly wish the weather cooperated as the backyard, the dock and Adirondack chairs were very inviting! The house was as described and made for a very homey weekend. ##### James S. Stayed 2 nights in May 2022 This review was submitted before 2018 and has not been verified. ### 10/10 Excellent #### morgan s. Aug 30, 2014 #### Family getaway This was a perfect family getaway, super friendly neighbors, Dianna was wonderful and very helpful! The home was comfortable and very easy to be in for our 4 person family. Clean and very well decorated. Kiddo had a great time kayaking and crabbing off the dock. Brought the dog and he had a great time swimming and playing with the neighborhood friendly doggies too. ##### morgan s. This review was submitted before 2018 and has not been verified. ### 10/10 Excellent #### John C., Haverford, PA, USA Jul 6, 2017 #### A Terrific Getaway Right on the Water 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. ##### John C. Stayed 3 nights in Jul 2017 This review was submitted before 2018 and has not been verified. ### 10/10 Excellent #### Elizabeth B. Sep 16, 2013 #### Midwest Traveller Our stay on the Chester River was great. We had plenty of room for four of us. The accommodations were clean and well appointed. We loved sitting out at the end of the dock and even put a fishing line in the water. The house is very secluded but only a few minutes away from Chestertown and any of the shopping we needed. We would go back again. ##### Elizabeth B. ### 10/10 Excellent #### Lyssa E. Jul 29, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Relaxing and very nice! My husband & I (with our 9 month old) really enjoyed our stay here! The place and outdoor area is even nicer in person than the pictures. It was very clean and had everything we needed while we were there. We really enjoyed the sandy area leading into the river and we loved floating in the river & using the paddleboard. We inquired with the host about where to get bait for fishing and they graciously brought some bait over for us. We really enjoyed our time and would stay here again! Thanks so much! ##### Lyssa E. Stayed 4 nights in Jul 2021 ### 10/10 Excellent #### Mike G. May 4, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautiful property The house is right on the river, with a dock just off the back yard. The sandy beach on the property was a hit with the kid. The owners are very helpful and communicative, and live right next door. We had access to kayaks and paddle boards and enjoyed the fire pit. The house itself is comfortable with fantastic river views. The osprey nest just off the dock is great, and we saw bald eagles during our stay. We would come back. ##### Mike G. 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