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Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Riverfront vacation home with kitchen and balcony

Photo gallery for Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Terrace/patio
Smart TV, fireplace, DVD player, video library
Smart TV, fireplace, DVD player, video library
3 bedrooms, desk, iron/ironing board, free WiFi
Fridge, microwave, oven, stovetop
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.

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 6195 sq m

Popular amenities

  • Dryer
  • Washer
  • Fireplace
  • Parking available
  • Breakfast included
  • Kitchen

Add dates for prices

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

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Rules

Beach towels are not provided. 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 neighborhood

Map
MD, Chestertown

What's nearby

  • Chestertown Dog Park - 5 min drive - 4.2 km
  • Washington College - 5 min drive - 4.9 km
  • Historical Society of Kent County Maryland - 7 min drive - 7.0 km
  • Chestertown Historic District - 7 min drive - 7.0 km
  • River Arts Chestertown - 7 min drive - 7.0 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.

How much is parking?

Onsite parking is available at the property.

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).

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Reviews

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town Reviews

9.8

Exceptional

10

Cleanliness

10

Location

10

Property conditions & facilities
Rating 10 - Excellent. 77 out of 85 reviews
Rating 8 - Good. 7 out of 85 reviews
Rating 6 - Okay. 1 out of 85 reviews
Rating 4 - Poor. 0 out of 85 reviews
Rating 2 - Terrible. 0 out of 85 reviews

Reviews

10/10 Excellent

steven s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything we needed was there. Owners next sore are super nice and hrphful.
Stayed 3 nights in Jul 2025

10/10 Excellent

Stephen H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful weekend. Thank you!
Stayed 3 nights in May 2025

10/10 Excellent

Lauriann S.

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.
Stayed 2 nights in Jul 2025

10/10 Excellent

Mark

Liked: Cleanliness, amenities, property conditions & facilities, communication
We had a wonderful stay. House was clean and charming, beds were comfy, hosts were attentive and nice, views were amazing. We enjoyed our visit very much.
Stayed 2 nights in Sep 2022

10/10 Excellent

Sun P.

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.
Stayed 3 nights in Nov 2024

10/10 Excellent

Bob R.

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!
Stayed 2 nights in Jun 2024

10/10 Excellent

Karman S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house!

Great house, very clean, nice location, very attentive owners!
Stayed 7 nights in May 2022

10/10 Excellent

Sarah R.

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.
Stayed 2 nights in Jun 2024

10/10 Excellent

Lisa V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend away

Excellent hosts. Everything we needed. Beautiful views!
Stayed 2 nights in Aug 2022

10/10 Excellent

John U.

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.
Stayed 7 nights in Oct 2022
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Laura D.

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.

10/10 Excellent

Allie P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great home

Home was very clean and neat. We enjoyed the snacks, and little touches.
Stayed 2 nights in Sep 2023

10/10 Excellent

Verified traveler

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!
Stayed 2 nights in Jul 2021

10/10 Excellent

Michael B., Arlington

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!
Stayed 3 nights in May 2021

10/10 Excellent

Amber U.

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!
Stayed 2 nights in Oct 2023

10/10 Excellent

Catherine M.

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!
Stayed 7 nights in Jul 2023

10/10 Excellent

Elamurugan S.

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.
Stayed 3 nights in Aug 2023

10/10 Excellent

Elsie D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding weekend

Very clean. Beautiful view.
Stayed 2 nights in Jun 2022
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Morgan G.

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!
This review was submitted before 2018 and has not been verified.

8/10 Good

Tim N.

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.
Stayed 3 nights in Sep 2016

10/10 Excellent

Patricia C., Northern Virginia

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.
Stayed 2 nights in Aug 2019

10/10 Excellent

James S.

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.
Stayed 2 nights in May 2022
This review was submitted before 2018 and has not been verified.

10/10 Excellent

morgan s.

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.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

John C., Haverford, PA, USA

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.
Stayed 3 nights in Jul 2017

10/10 Excellent

Ellen H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Memorial weekend stay

Comfortable, well equipped rental home. Enjoyed all the amenities, with the dock and deck and lovely views of the river. Enjoyed sunrise one morning and watching the river come to life with the birds, and early morning scullers rowing. Had a cookout one night and lit a fire in the fire pit. So fun.
Stayed 3 nights in May 2023