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

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February 2025

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2 bedrooms, iron/ironing board, free WiFi, bed sheets
Unclassified image, 2 of 24, button
Terrace/patio
Smart TV, fireplace, DVD player, video library
Fridge, microwave, oven, stovetop

Reviews

9.8 out of 10

Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 6130.1 sq m

Popular amenities

  • Breakfast included
  • Parking available
  • Pet-friendly
  • Outdoor space
  • Washer
  • Barbecue grill

Explore the area

Map
Chestertown, MD
  • Washington College
    7 min drive
  • Arby's
    6 min drive
  • Aberdeen Station
    82 min drive
  • Baltimore, MD (MTN-Martin State)
    110 min drive

Room options

Similar properties

Private Dock

Waterfront Retreat with Private Dock and Beach

Kitchen
Free WiFi
Air conditioning
Parking available
5.0 out of 5, Exceptional, (17)
The price is CA $252
per night
CA $448 total
includes taxes & fees
7 Jan - 8 Jan
Waterfront Retreat with Private Dock and Beach

About the area

Chestertown

On river.You'll be within 6 miles (10 km) of Washington College and 9 miles (15 km) of Rolphs Wharf Marina. Betterton Beach is within 16 miles (25 km) and Rock Hall Harbor is within 20 miles (32 km).
View more Vacation homes in ChestertownOpens in a new window

What's nearby

  • Washington College - 7 min drive
  • Garfield Center for the Arts at the Prince Theater - 8 min drive
  • Historical Society of Kent County Maryland - 8 min drive
  • River Arts Chestertown - 8 min drive
  • Rolphs Wharf Marina - 17 min drive

Getting around

  • Baltimore, MD (MTN-Martin State) - 110 min drive

Restaurants

  • ‪McDonald's - ‬7 min drive
  • ‪Dining Hall - ‬7 min drive
  • ‪Procolino Pizza - ‬6 min drive
  • ‪China House - ‬6 min drive
  • ‪The Freeze - ‬6 min drive

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, 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 2 large bedrooms(2 queen beds + 1 twin.)Both bedrooms have a smart TV. One has 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 the best 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. Both 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) hammock 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, twin bed added in a bedroom, 4 smart tv's & ceiling fans. 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, HP festival first weekend in Oct, 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 manager

Dianna or Russell

Languages

English

Property amenities

Beach

  • Near the beach
  • Beach towels

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking
  • Car required

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Paper towels
  • Cookware/dishes/utensils

Dining

  • Free breakfast available
  • Dining table

Bedrooms

  • 2 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathrooms

  • 1.5 bathrooms
  • Bathtub or shower
  • Soap
  • Shampoo
  • Toilet paper
  • Towels provided
  • Hair dryer

Living spaces

  • Fireplace
  • Living room

Entertainment

  • Smart TV with cable/satellite service
  • DVD player
  • Video library
  • Games

Outdoor areas

  • Patio
  • Barbecue grill
  • Outdoor furniture
  • Firepit
  • Dock

Laundry

  • Washing machine and dryer
  • Near laundromat

Comfort

  • Air conditioning
  • Ceiling fan
  • Heating

Pets

  • Pet friendly
  • 2 total (up to 50 lbs per pet)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Tile flooring in public areas
  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Wet bar

Location highlights

  • On the river
  • On the waterfront
  • Near a health or beauty spa
  • Near a hospital
  • Near outlet shopping

Things to do

  • Water sports equipment
  • Fitness facilities nearby
  • Kayak on site
  • Swimming nearby
  • Hunting nearby
  • Water tubing nearby
  • Winery tours nearby
  • Cave exploring nearby
  • Fishing nearby
  • Wildlife and game walks nearby
  • Hiking nearby
  • Water skiing 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 installed (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • At least 80% lighting from LEDs
  • Recycling
  • Water-efficient showers only
  • Unit size: 1400 sq ft (130.1 sq m)

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

Pets

  • Pets are welcome
  • Maximum 2 (weight limit: 50 lbs per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees
  • Note from host: 4 pets weighting over 60lbs, please contact owner.

Children and extra beds

  • Children are welcome.

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

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

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 72 out of 80 reviews" "
Rating 8 - Good. 7 out of 80 reviews" "
Rating 6 - Okay. 1 out of 80 reviews" "
Rating 4 - Poor. 0 out of 80 reviews" "
Rating 2 - Terrible. 0 out of 80 reviews" "

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

Reviews

10/10 Excellent

Sun P.

Liked: Cleanliness
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

Sarah R.

Liked: Cleanliness
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

Bob R.

Liked: Cleanliness
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

Amber U.

Liked: Cleanliness
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

Allie P.

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

10/10 Excellent

Catherine M.

Liked: Cleanliness
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
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

Maureen H.

Liked: Cleanliness
Lovely place!
We had a lovely stay at this cottage on the water. The cottage had its own dock, deck, mini beach, grassy yard with kayaks, paddle boat, stand up paddles —enough for everyone. The birding is brilliant. The hosts have created an environment that welcomes birds. On our morning paddle, we saw bald eagles, ample herons, other sea birds and an otter, snakes and turtles. The house has everything you need. It’s very comfortable with a full kitchen, games, plenty of different spaces to relax and enjoy your time with family. The hosts are super considerate and kind people. They know how to make a space that’s great for your holiday. Book now! You won’t regret it!
Stayed 2 nights in Jul 2023

10/10 Excellent

Bill F.

Liked: Cleanliness
Eastern Shore Visit
My wife and I and our 3 grandchildren had an absolutely fabulous time on the Chester River. The cottage accommodated us very well with a modern kitchen and 2tv spaces The dock offered a fishing spot and beautiful views. Our hosts, Dianna and Russ made the experience special by making sure the kids knew how to use the kayaks and where to swim and generally helping them enjoy themselves. A short ride to Rockhall for crabs and a fishing trip topped off a wonderful Eastern Shore Visit.
Stayed 3 nights in Jul 2023

10/10 Excellent

Doris O.

Liked: Cleanliness
Escape
I picked this property out based on the listing description. My family and guests were skeptical coming into the weekend about what I had picked out! Everyone, from start to finish had a blast! We kayaked, threw fishing lines in the water. We offered to take the family to dinner the first night and they asked for burgers on the grill! We made s’mores. Watched fireworks from the pier. Played board games, watched movies. Went to a festival nearby. Had a few meals out at local spots. There were many special touches that could be pointed out. I have already shared with my friends. I hope to get back again. Unplug, relax, enjoy! Heaven.
Stayed 4 nights in Jul 2023

10/10 Excellent

Ellen H.

Liked: Cleanliness
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

10/10 Excellent

Cindy R.

Liked: Cleanliness
Wonderful Chester River Property
Very clean, tidy home directly on the Chester river. While we were here for an event at Washington College in February, the property is gorgeous and we definitely want to return during warmer months to enjoy Chestertown and sipping wine on the deck overlooking the river. The house has lots of seating throughout and we enjoyed playing card games at night with the kids. Super clean house, and kitchen is incredibly functional. Can't wait to return!
Stayed 2 nights in Feb 2023

10/10 Excellent

John U.

Liked: Cleanliness
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

10/10 Excellent

Verified traveller

Liked: Cleanliness
Wonderful well-equipped and comfortable house!
We visited Chestertown for a fall weekend of bird-watching and exploring. When we arrived, a bald eagle was perched right near the dock, so our birdwatching got off to a great start. We were delighted with the house- comfortable beds, immaculately clean, well-equipped with everything we needed, and lots of nice little touches to make our stay comfortable and enjoyable. One of our two nights was rainy and cold, so we stayed in and made dinner. We found everything we needed in the kitchen. We will definitely return and love that we were able to bring our dog. Thanks for a great stay!
Stayed 2 nights in Oct 2022

10/10 Excellent

Mark, Kennett Square

Travelled with family, Travelled with pets
Liked: Cleanliness, amenities, property conditions & facilities
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

Lisa V.

Liked: Cleanliness
Weekend away
Excellent hosts. Everything we needed. Beautiful views!
Stayed 2 nights in Aug 2022

10/10 Excellent

Debbie L.

Liked: Cleanliness
Stay
It was fun.
Stayed 3 nights in Aug 2022

10/10 Excellent

Karin C.

Liked: Cleanliness
A lovely respite
We came for a few days to relax on the water. The view was wonderful, and we loved sitting on the dock watching the river. Diana was welcoming and informative, filling us in on the local bird life, from ducks to Great Horned Owls. A pair of ospreys were still guarding their nest just off the dock and we saw an eagle and a vulture. Unfortunately we were there during an intense heat wave which discouraged us from kayaking, but we look forward to it next time. The house is wonderfully complete with comfortable furniture and a well-equipped kitchen and is meticulously clean. We would have liked to stay longer and hope to return.
Stayed 3 nights in Aug 2022

10/10 Excellent

Jeff B.

Liked: Cleanliness
Title
Great views!
Stayed 3 nights in Jun 2022

10/10 Excellent

Elsie D.

Liked: Cleanliness
Wedding weekend
Very clean. Beautiful view.
Stayed 2 nights in Jun 2022

10/10 Excellent

Karman S.

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

10/10 Excellent

Glenn K.

Liked: Cleanliness
Amazing Property
We had an amazing time staying on this property. We were visiting Washington college right by and it was a great location! Dianna was great and was responsive with everything asked, friendly neighbors as well! Would recommend this place for anyone
Stayed 2 nights in Apr 2022

10/10 Excellent

James S.

Liked: Cleanliness
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

10/10 Excellent

Lizeth M., Virginia

Liked: Cleanliness
Great place
This house is amazing, comfy, great view
Stayed 2 nights in Oct 2021

10/10 Excellent

Sheldon J.

Liked: Cleanliness
Very comfortable and relaxing.
Wonderful views of eagles and other birds. Enjoyed kayaking on River.
Stayed 7 nights in Sep 2021