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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

Waterfront holiday home with kitchen and balcony

Photo gallery for Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

View from deck of brick patio, fire pit area, & pier w/ separate floating dock.
Sunset view from backyard.
View of Chestertown & Chester River Bridge from our property
New hot tub on deck - use in autumn and winter mostly. Propane grill new in 2024
Welcome to our home.

Reviews

10 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 8195.1 sq m

Popular amenities

  • Dryer
  • Washer
  • Barbecue grill
  • Fireplace
  • Parking available

Explore the area

View map
  • Place, Historical Society of Kent County Maryland
  • Place, Chestertown Historic District
  • Place, Washington College
  • Airport, Easton, MD (ESN-Easton - Newnam)

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Single Beds and 1 Crib

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

About this property

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

My place is located in a quaint neighborhood close to downtown Chestertown; 1 mile walk. This home has a large screened porch & inviting outside patio. Cruise the Chester River with the canoe or two paddle boards provided. Feel free to bring your boat & dock at our deep water pier. Crabbing* (trap & net), fishing (2 rods), & biking (4 provided) are also fun activities to enjoy here at the property. Fire pit (all seasons), indoor fireplace, and outdoor hot tub (available October through the end of April). We will do our best to keep hot tub in working order, but cannot guarantee it will be in working condition 100% of the time. It does take longer to get technicians out here. However we will do our best. We look forward to your stay. All are welcome.
*Crabbing is not as plentiful as years past, and only during the hot summer and early autumn.

Add dates for prices

Amenities

Hot tub
Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space

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Exterior
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
10.0 out of 10, (84 reviews)
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 12:00 PM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Deposit will be forfeited if there is a gathering or event without permission. No guests of guests are allowed unless approved by owner.
No parties. No gatherings over the 8 guests who are listed in the rental request. No pets!
No pets.

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
On-site 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 not indicated whether there is a smoke detector on the property

About the area

Chestertown

Located in Chestertown, this holiday home is in the city centre and on the waterfront. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Crumpton Auction and Hazel Miner Monument.
View more Holiday homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Historical Society of Kent County Maryland - 16 min walk - 1.4 km
  • Chestertown Historic District - 17 min walk - 1.5 km
  • River Arts Chestertown - 4 min drive - 1.0 km
  • Washington College - 4 min drive - 1.3 km
  • Rolphs Wharf Marina - 12 min drive - 7.9 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 104 min drive

Restaurants

  • ‪Royal Farms - ‬16 min walk
  • ‪Royal Farms - ‬3 min drive
  • ‪Dunkin - ‬4 min drive
  • ‪Procolino's - ‬4 min drive
  • ‪Subway - ‬3 min drive

Frequently asked questions

Is Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown?

Checkout is at 12:00 PM.

Where is Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown located?

Located in the heart of Chestertown, this holiday home is within 1 mile (2 km) of Kings Town Park, Historical Society of Kent County Maryland and Chestertown Historic District. Garfield Center for the Arts at the Prince Theater and Sumner Hall are also within 1 mile (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 103 out of 106 reviews
Rating 8 - Good. 2 out of 106 reviews
Rating 6 - Okay. 1 out of 106 reviews
Rating 4 - Poor. 0 out of 106 reviews
Rating 2 - Terrible. 0 out of 106 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

David C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a great visit with relatives in Chestertown. House and property were excellent. Kitchen is large and well-equiped. Communication with owner, from pre-booking to check-in to exit, was easy and timely. House has a large living room, dining room table that seated eight and a screened porch and lovely outdoor sitting areas. Great view of river. Easy walk to town. Top notch overall.
Stayed 3 nights in Jul 2025

10/10 Excellent

Deborah P.

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

Graduation weekend

We had a wonderful weekend stay with family for our daughter’s graduation from Washington College. The location was perfect, so convenient to town and campus. The house was lovely and immaculate. We highly recommend!
Stayed 3 nights in May 2025

10/10 Excellent

Lisa V.

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

Great house and location

Perfect and peaceful weekend getaway.
Stayed 2 nights in Jul 2020

10/10 Excellent

Ira C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This rental was an ideal choice for our visit to Chestertown. Communication with the hosts was consistently clear, readily available, and very transparent, making the entire process smooth and stress-free. The house is beautifully situated on the Chester River, offering spectacular views and frequent sightings of birds, whose lively antics on and around the river provided endless entertainment. The river is ever changing in its offerings to the occupants. Exploring the surrounding area was easy and enjoyable. The bakeries located in and around High Street, downtown, were just a one mile walk away, which took us over the Chester River Bridge and through the charming, historic colonial streets The rental featured excellent outdoor appointments. Although we did not use the hot spa, canoe, paddleboard, fishing rods, or croquet set, we thoroughly enjoyed relaxing around the fire pit in Adirondack chairs and taking the tandem kayak out on the river. The Chester River proved perfect for kayaking, and the screened porch at the back of the house provided a peaceful spot for relaxation and quiet enjoyment. Access by vehicle and parking were exceptionally easy and convenient. The house was very comfortable with 3 bedrooms perfect for couples and a nice 4th with twin beds. The 3 bathrooms were roomy and well lit. The kitchen was perfect for using goodies from the farmer’s market. We left feeling our visit with family was well celebrated & when not touring, relaxed. We would return!
Porch with an evening view
The Chester River Flotilla has landed
Chestertown harbor only 1 mile walk away
Stayed 14 nights in Oct 2025

10/10 Excellent

Sara S.

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

New Favorite

We have stayed at various places in this area over the years and this one checked all the boxes.
Stayed 4 nights in Jun 2024

10/10 Excellent

Irene M.

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

Great stay on the Chester River

Great place for our family stay. Beautiful sunsets, loads of fun on the river, and a responsive owner!! Thanks, Beth!
Stayed 6 nights in Aug 2022

10/10 Excellent

Allison N.

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

Wonderful Weekend

This house is a gem! The property is fantastic, with such a beautiful backyard.
Stayed 2 nights in Apr 2024

10/10 Excellent

Daniel L.

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

Nice base for a wedding weekend

We enjoyed our stay!! This home is lovely. We just wish we had more there as we were very busy with wedding events!!
Stayed 2 nights in Jun 2022

10/10 Excellent

Donna D., Williamstown NJ

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

Beutiful

Beths house was clean and beautiful. The backyard was awesome. We had so much fun on the paddle boards and canoes.
Stayed 3 nights in May 2019

10/10 Excellent

Gary W.

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

A beautiful getaway...

This house is perfect for a large family, with room for mom, dad, and at least four kids. That's not even counting couch sleepers. The property is exactly what you'd expect on the river with a nice long dock for fishing and crabbing, a spacious screened-in porch, and wonderful view of the sunset. The neighbors are great. They even brought us over some crab balls, which were delicious. Will definitely stay here again.
Stayed 4 nights in Aug 2024

10/10 Excellent

Nora K.

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

Son's Wedding - September 2023

This house was lovely and fit our family perfectly to prepare for our son's wedding in Chestertown. The host (Beth) was very responsive to any questions we had upon our arrival.
Stayed 3 nights in Sep 2023

10/10 Excellent

Bobbi S.

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

Beautiful Property in Chestertown!

Three couples stayed 2 nights for a wedding. Each couple had their own bathroom. The house is well furnished, has seating outdoors and a huge screened in porch right on the river. It was so relaxing to sit in the sun or in the shade. The host is very responsive and was wonderful to deal with! We all loved it and want to come back and stay when we can spend more time at the property. Chestertown was charming and fun to visit. Cannot recommend this property enough, you won’t be disappointed!
Stayed 2 nights in Jun 2024

10/10 Excellent

Marlene I., Putnam Valley, New York

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

Just a weekend

Overall this is a beautiful rental. The view is amazing and the house is decorated so nicely. My husband loved it and wanted to plan another visit for a longer stay. One of the nicest parts of the rental was the departure instructions. They were easy and not excessive as we have experienced before in other rentals. Thanks for the hospitality!
Stayed 2 nights in Jun 2023

10/10 Excellent

Aaron C.

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

Awesome place...

2 Family vacation stay was excellent. The house is nicely set up for lots of people to be together in and outside. The yard is big and open with trees for shade and nice fire pit and hammock. If you love fishing and boating like we do, you'll love it here as there is a large dock and plenty of fish to catch. We caught catfish all day and my son caught the largest fish ever right from the yard. Blue catfish that had to be about 48" and roughly 4- to 50 lbs. Neighborhood is very nice and there is a nice quaint town in walking distance across the bridge. Awesome place for a multi-family getaway. Highly recommend.
Stayed 5 nights in Apr 2024

10/10 Excellent

Brent P.

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

Beautiful view!!

My family (4 adults and 4 kids) had the most relaxing and enjoyable time staying at Beth’s home with a beautiful view!! We loved the open layout of the house and the fact that everything was on one floor, and the real highlights were the amazing (and huge!) screened porch overlooking the backyard with patio, fire pit and river!! And the hydrangea were gorgeous! My kids had a blast using the provided fishing poles, stand up paddle boards and canoe. We bought seafood and had a feast on the porch one night. We went into town for ice cream and to walk around. The houses in Chestertown are so very charming! It was not crowded or touristy unlike some other parts of the Eastern Shore — a “breath of fresh air.“ Beth was VERY accommodating to us and she always responded to me promptly. We would recommend her home!
Stayed 3 nights in Jun 2020

10/10 Excellent

Mara F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was perfect for our stay; the home is beautiful and had all the space and amenities were exactly what we needed. The home was clean and very cozy, we felt at home for the event we were attending, we could not have asked for more. If you are attending a wedding at the
Stayed 2 nights in Oct 2025

10/10 Excellent

Heidi J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
In town for wedding and stayed three nights. Pictures really don’t show the real beauty of this home. Quiet location, beautiful water views, well stocked and clean. Plenty of room for everyone. The host was very accommodating! Would definitely stay again.
Stayed 3 nights in Sep 2025

10/10 Excellent

Irene M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home with full amenities and wonderful view of the Chester River .
Stayed 6 nights in Aug 2025

10/10 Excellent

Michelle R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful location on the Chester River. Easily hosts a number of guest for an evening dinner on the porch. It’s proximity to Chestertown makes it a perfect location.
Stayed 3 nights in Aug 2025

10/10 Excellent

Jean D.

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

Lovely house

We enjoyed our stay at this lovely home while visiting family in Chestertown. The house is very well equipped and comfortable with everything we needed for family meals and a relaxing break.
Stayed 3 nights in Jul 2025

10/10 Excellent

Molly J.

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

Relaxing Girls Getaway Weekend

Beautiful views of the water. Amazing brand new hot tub. Very spacious layout of the house.
Stayed 2 nights in Mar 2025

10/10 Excellent

Karen F.

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

Fantastic!

This property was absolutely perfect for our girl’s weekend. The location was convenient to town but still felt very private with a picturesque view of the river. The house was beautifully furnished, sparkling clean, and well appointed. We truly felt like a guest in someone’s home. We would love to stay again!
Stayed 2 nights in Mar 2025

10/10 Excellent

David C.

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

Outstanding

House was impeccable. Perfect location within walking distance to downtown Chestertown. Beth, the owner, was responsive and tended to our needs immediately. Highly recommend this beautiful, friendly home.
Stayed 2 nights in Nov 2024

10/10 Excellent

Tim S.

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

Lovely house in a beautiful location in a charming town.

House was spotless and well appointed and as represented in the ad. Had a family gathering in town so didn't get to spend as much time at the house as we would have liked. Good communication with owner. Recommended.
Stayed 2 nights in Oct 2024

10/10 Excellent

kirk d.

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

Beautiful Riverside Spot

This wonderful home sits right on the Chester River with a generous back yard and a dock. We kayaked and SUPed on the Chester River and thoroughly enjoyed our stay. Just over the bridge from Chestertown so easy access to shops, coffee, etc.
Stayed 2 nights in Sep 2024

About the host

Hosted by Beth Connor

Host profile image
My husband and I live in Ellicott City and have wanted to buy a home on the water. We found a wonderful opportunity to purchase a great home to gather with our adult children, in a charming part of the world, that is not too far from our main residence. We hope that you too can enjoy our dream home with your family (and friends).

Why they chose this property

This home has a mix of antiques, and comfortable new, stylish furniture that today's vacationers want. The home was renovated with the most impeccable taste (we were fortunate to buy it this way). It has just about everything you would need to enjoy time together with your family and friends. From the huge screened porch with amazing new, chic outdoor furnishings (including an 8 foot farm table for crab picking or fancy dining), to a patio, hammock, canoe, paddle boards, fishing rods, crabbing net and trap, along with 4 adult bikes, this home will prove to be one of your family's more memorable experiences together. October through the end of April you can enjoy the use of the hot tub and fire pit. If you want to just relax indoors there is a large screened tv with a big sectional and chair to gather together. In the colder months, you can also enjoy the wood-burning fireplace (next to tv).

What makes this property unique

Walking/biking distance to Chestertown. Waterfront with pier. Gorgeously updated home with smart furnishings.

Languages:

English
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