Skip to main content
Entire home

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

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 8

Popular amenities

  • Hot tub on site
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Chestertown, MD
  • Place, Kings Town Park
    ‪3 min walk‬
  • Place, Washington College
    ‪23 min walk‬
  • Place, Historical Society of Kent County Maryland
    ‪20 min walk‬

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

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Exterior detail
BAYSIDE BUNGALOW
Rock Hall
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space
  • Parking available
10.0 out of 10, Exceptional, (53 reviews)
BAYSIDE BUNGALOW

House Rules

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

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

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. Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center are also worth visiting.
View more Holiday homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Kings Town Park - 3 min walk - 0.3 km
  • Chestertown Historic District - 19 min walk - 1.6 km

Getting around

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

Restaurants

  • ‪Milano's Pizzeria - ‬3 min drive
  • ‪McDonald's - ‬4 min drive
  • ‪Dunkin - ‬4 min drive
  • ‪Royal Farms - ‬3 min drive
  • ‪Procolino's - ‬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.

How much does it cost to stay at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown?

As of 7 May, 2026, prices found for a 1-night stay for 2 adults at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown on 27 Oct, 2026 start from S$844, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown?

On-site parking is available at the 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. 106 out of 109 reviews
Rating 8 - Good. 2 out of 109 reviews
Rating 6 - Okay. 1 out of 109 reviews
Rating 4 - Poor. 0 out of 109 reviews
Rating 2 - Terrible. 0 out of 109 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Olin G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Always love staying here.
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

sharon w.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home on the river! Kitchen fully stocked, all bedrooms and livings space very comfortable. Porch and fire pit enjoyed by all. Would definitely recommend and stay again.
Stayed 2 nights in Nov 2025
Response from VrboOwner on 3 Dec, 2025
Thank you Sharon for your wonderful review. I too enjoy our porch and am glad you and your guests enjoyed their stay. Thank you for being such a good guest.
Verified

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
Response from VrboOwner on 23 Aug, 2025
Thank you Michelle for returning to this home that is do familiar to you. I’m glad you enjoyed entertaining on the porch.
Verified

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
Response from VrboOwner on 28 Oct, 2025
Thank you Mara for the wonderful review. I’m so glad the house worked for your needs. I really appreciate such nice comments about the house.
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Response from VrboOwner on 28 Mar, 2025
Thanks for the great review. I'm glad you enjoyed our new hot tub. I appreciate you taking the time to review, and welcome your return if you decide to come back.
Verified

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
Verified

8/10 Good

Patricia C.

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
Verified

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
Response from VrboOwner on 4 Sept, 2022
Thank you Irene! I love having you and your family and appreciate your coming back each year.
Verified

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
Response from VrboOwner on 28 Mar, 2025
Thank you Karen for such a wonderful review! I am glad that you enjoyed your stay, and would certainly welcome you as our guest again.
Verified

10/10 Excellent

Irene M.

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
Verified

10/10 Excellent

Irene M.

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
Verified

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
Verified

10/10 Excellent

Bill D.

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

Great House and perfect location. Porch and yard were amazing

Great
Stayed 3 nights in May 2023
Verified

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
Verified

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
Response from VrboOwner on 6 Oct, 2024
Thank you Kirk for the great review. I’m so glad you got to enjoy the SUPs, kayak and back yard. I appreciate your choosing our home for your stay in Chestertown.
Verified

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
Response from VrboOwner on 23 Jun, 2022
Thank you Daniel. I hope you had a good time at the wedding!
Verified

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
Verified

10/10 Excellent

Linda K.

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

Fabulous!

Was a great property with peaceful views and plenty of wonderful amenities. Will definitely return!!
Stayed 3 nights in Jun 2019
Response from VrboOwner on 18 Mar, 2020
Thanks Linda. I know that you left our property in pristine condition. Thank you so much, and I look forward to your return!
Verified

10/10 Excellent

Gary j.

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
Verified

10/10 Excellent

jamie h.

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

Another great time at this beautiful home

This is our second time staying at this beautiful home on the water. The house has everything you need to relax. We crabbed and fished from the pier, and enjoyed the screened porch. Looking forward to our third trip next year here. Thanks Beth for allowing us to stay. !
Stayed 5 nights in Aug 2020
Response from VrboOwner on 11 Nov, 2020
Thank you Jamie for the nice review. I am so glad you were able to get some crabbing and fishing in with your visit. And thank you so much for booking already for next year. You are a terrific guest, and much appreciated.

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
Tell us how we can improve our siteShare feedback