Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

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Entire home

New floating dock gives easy access to the water. Great for sunbathing too!

Patio & fire pit are fun for entertaining. Don't forget relaxing on the hammock.

Deck with grill, outside shower, and hot tub (cooler months only).

Overview
Amenities
Policies
Location
Host

Exceptional

4 bedrooms3 bathroomsSleeps 8195.1 sq m

Popular amenities

Hot tub
Dryer
Washer
Fireplace
Parking available
Barbecue grill

Explore the area

Chestertown, MD

Historical Society of Kent County Maryland
‪16 min walk‬
River Arts Chestertown
‪2 min drive‬
Washington College
‪2 min drive‬
Aberdeen, MD (APG-Phillips Army Airfield)
‪92 min drive‬

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

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.

Property manager

Beth Connor

Languages

English

Add dates for prices

Amenities

Hot tub

Kitchen

Washer

Dryer

Air conditioning

Outdoor space

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Similar properties

Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft

Pool
Kitchen
Pet-friendly
Air conditioning

House Rules

Check in after 4:00 PM

Minimum age to rent: 30

Check out before 12:00 PM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

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. Historical Society of Kent County Maryland and Betterton Historic District are local landmarks, and some of the area's activities can be experienced at Rolphs Wharf Marina and Cassinelli Winery and Vineyards. Crumpton Auction and Hazel Miner Monument are also worth visiting.

Chestertown, MD

What's nearby

Historical Society of Kent County Maryland - 16 min walk - 1.4 km
Garfield Center for the Arts at the Prince Theater - 17 min walk - 1.5 km
River Arts Chestertown - 2 min drive - 1.8 km
Washington College - 2 min drive - 2.0 km
Rolphs Wharf Marina - 10 min drive - 6.9 km

Getting around

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

Restaurants

‪McDonald's - ‬4 min drive
‪Dining Hall - ‬4 min drive
‪Procolino Pizza - ‬4 min drive
‪China House - ‬4 min drive
‪The Freeze - ‬4 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 Garfield Center for the Arts at the Prince Theater. Wilmer Park and Washington College are also within 1 mile (2 km).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Molly J.

26 March 2025

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.

17 March 2025

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.

3 November 2024

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.

24 October 2024

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.

22 September 2024

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

8/10 Good

Patricia C.

11 September 2024

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

Chestertown VRBO

The property was very nice. Perfect for our group attending a wedding.

Stayed 3 nights in Sep 2024

10/10 Excellent

Gary W.

3 September 2024

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

Irene M.

19 August 2024

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

Another great stay !

We had a great family vacation at this property … again The home and grounds are a good fit for a wonderful stay on the Chester River. And the property owner is welcoming and responsive.Thank you, Beth!

Stayed 6 nights in Aug 2024

10/10 Excellent

Harriet S.

26 June 2024

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

Mother-of-the-Bride Wedding Weekend

Spectacular, perfect calm, finely appointed - I just wish I realized I couldn't spend enough time there with my obligations and only-weekend schedule. Provided me late-night respite with a fabulous bed for a great night's sleep and morning shower, twice, leaving the five friends behind to follow later. We decidedly determined we'd have a reunion so we could just sit riverside and enjoy the gorgeous, hospitable property. Book it now!

Stayed 2 nights in Jun 2024

10/10 Excellent

Sara S.

24 June 2024

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

Bobbi S.

17 June 2024

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

sue b.

5 June 2024

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

LOVE this 5 STAR HOME!

Just returned from out two night stay at the Connor's waterfront home in Chestertown. It was FABULOUS. We were in this lovely historic town for a family wedding at Britland Manor, and were fortunate to find this charming, well appointed waterfront home. It was perfect for our family of 6 adults and a toddler, providing plenty of space both indoors and out, plus a well appointed kitchen. Unfortunately we didn't have time to use paddleboards, canoe or any of the other outdoor activities available, but hopefully you will! Looking forward to a return visit. Beth (owner) was very responsive and helpful. Thank you, Beth, for sharing your home with our family!

Stayed 2 nights in May 2024

10/10 Excellent

Melanie D.

23 May 2024

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

Simply Perfect

The house was just as described online. We spent so much time out on the beautiful screened in porch and in the backyard by the river. The bedrooms were spacious and lovely. The kitchen was well stocked with dishes, appliances and everything we needed for family meals. We will definitely try and vacation there again.

Stayed 3 nights in May 2024

10/10 Excellent

Allison N.

28 April 2024

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

Aaron C.

27 April 2024

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

Ernest D.

2 April 2024

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

I'm kicking myself for leaving earlier than I could have!

This rental saddened me because I didn’t stay as long as I could have!!! We were amazed at the cleanliness and the “homeliness” of the dwelling. When I walked in the tranquility was amazing. My wife viewed the other rooms before our family arrived. She is a stickler for cleanliness and order. To show how much she appreciated this listing she informed me that she had brought cleaning supplies just in case (she is a cleanliness person from her youth). We were ready (from upbringing and habit when you reside in another’s home, and it did feel like it!) you are to leave the place just as clean if not cleaner than when you found it. But the instructions were clear to the cleaning of it after we signed out. The rooms were so comfortable that it was unreal. EVERYTHING needed was right there. All we really had to do was come, bring “some” food if we wanted to cook and care for the host’s property. I can’t end the praises for the host, the property, the ambiance and the comfort. While this holiday had mixed emotions and feelings (my sister and I are the remaining family members) the comfort and home feeling of this rental eased everything. While we had one three-year-old with us, I could have had other grandchildren WITH SUPERVISION of course with us. I can only speak about our room when I say I didn’t want to leave there because of the comfort! THIS this is MY special place!

Stayed 4 nights in Mar 2024

10/10 Excellent

Cat S.

25 March 2024

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

family gathering

This house is perfect for a large group to be together. We had terrible weather, but were comfortable in the large family room and dining room. I would like to visit again when the weather is warmer.

Stayed 2 nights in Mar 2024

10/10 Excellent

Greg

23 September 2023

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

Great Stay

We enjoyed our stay very much. The house was clean and well-appointed. We had 3 generations with us and everyone was comfortable. We all spent many hours outside at the river’s edge relaxing and enjoying the views. Beth was responsive to our questions and very accommodating to our special needs. We won’t hesitate to book here again!

Stayed 4 nights in Sep 2023

10/10 Excellent

Nora K.

10 September 2023

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

Irene M.

24 August 2023

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

Great place!

We had ANOTHER great stay at your place on the river. Thanks, Beth

Stayed 6 nights in Aug 2023

10/10 Excellent

Gary j.

13 August 2023

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

We wanted to go somewhere

We wanted a vacation that would be easy for a 2-month-old baby and this place was perfect we enjoyed playing games at the house, fishing on the dock, swimming and kayaking ,star gazing from the dock.house was great!

Stayed 7 nights in Aug 2023

10/10 Excellent

Kimberly M.

29 July 2023

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

Amazing family trip

This was unexpectedly wonderful. We really feel like the photos in the listing do not do this home justice. When you walk in this home, you were walking into an immaculate space, well thought out and will planned. Every room is fully stocked with everything you need. We made the mistake of stopping at a local grocery store for things like olive oil, and toilet paper. Completely unnecessary. Beth has this home completely stocked and ready for everyone! The kitchen had every appliance and gadget that we needed. The backyard was incredible. We wish that the person that mows the lawn didn’t randomly show up while we were outside. But aside from that, the outdoors were amazing. It was quiet, it was peaceful. The neighbors were delightful. We had intended on going crabbing, which did not work out because we were a little early in the season. But we still enjoyed the canoe, fishing, kayaking and sitting in the outside screened in porch. The showers are huge and luxurious. The beds were more comfortable than what we have at home. There is a reason this home has five stars. And that is because Beth goes the extra mile in every area of the house to make sure that the people that stay there truly feel like they’re at home. Beth responded to every message in a timely manner. She left very clear instructions on how everything works in the home. You can tell she is incredibly organized. I recommend this home to anyone who wants a luxurious family vacation.

Stayed 4 nights in Jul 2023

10/10 Excellent

Annette V., Verona, NJ

24 July 2023

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

Perfect Place

This house was perfect for us! We had everything we needed for our extended family. Plenty of room. Big screened in porch. Nice fire pit. Loved to take out the canoe and paddleboard out on the water. Nice and cool in the shade and warm on the dock. Everyone had so much fun! Clearly a much loved house. So close to town and to a day trip to Annapolis.

Stayed 4 nights in Jul 2023

10/10 Excellent

Marlene I., Putnam Valley, New York

5 June 2023

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

8/10 Good

Steven T.

22 May 2023

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

Graduation Weekend

I cannot overstate the beauty and peacefulness of this location. We had our family ages 5-85 together to celebrate my son’s graduation. The home easily accommodated the unique needs of this wide age range. We are so grateful to have been able to spend special family time here.

Stayed 3 nights in May 2023

About the host

Hosted by Beth Connor

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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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

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Reviews

Popular amenities

Explore the area

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

Bedroom 2

Bedroom 3

Bedroom 4

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

About this property