Entire home

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

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

A lakeside patio with outdoor seating and a view of the lake.
A spacious living area with a kitchen, dining table, and a large window providing natural light.
A residential house with a front porch, a lawn, and a driveway.
A living room with a stone wall, a fireplace, a television, a bookshelf, and a sofa.
An indoor basketball court with multiple hoops, a polished floor, and a high ceiling with visible structural beams.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Paddleboard available
    A rare find — hit the water on a paddleboard right here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Chestertown Historic District

Popular amenities

  • Balcony or patio
  • Spa pool on site
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Internet

Explore the area

View map
Chestertown, MD
  • Place, Kings Town Park
    ‪3 min walk‬
  • Place, Chestertown Historic District
    ‪19 min walk‬
  • Place, Washington College
    ‪4 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪55 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

Add dates for prices

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10.0 out of 10, Exceptional, (92 reviews)
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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 Schooner Sultana 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
  • Historical Society of Kent County Maryland - 4 min drive - 0.6 km
  • River Arts Chestertown - 4 min drive - 1.0 km
  • Washington College - 4 min drive - 1.3 km

Getting around

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

Restaurants

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

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 4 Nov 2026, prices found for a 1-night stay for 2 adults at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown on 7 Mar 2027 start from AU$1,552, 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. 115 out of 118 reviews
Rating 8 - Good. 2 out of 118 reviews
Rating 6 - Okay. 1 out of 118 reviews
Rating 4 - Poor. 0 out of 118 reviews
Rating 2 - Terrible. 0 out of 118 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great view and home for a family weekend getaway or weeks long vacation. It is convenient to town and easy to get to 213 north or south.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home is clean, host responsive , and kitchen well stocked with tools, pots and pans. Easy parking too.
Stayed 6 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We truly enjoyed our mini family vacation at this beautiful home! The house has a perfect set up to enjoy the water views. Host was great at responding quickly with any questions. Would love to come back again.
Stayed 2 nights in Jul 2026
Response from VrboOwner on 17 Aug 2026
Thank you Candace for the wonderful review. I’m glad you enjoyed our home on the Eastern Shore. We would love to have you back.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property, right near Chestertown
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

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

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay in Chestertown. The house was really nice, and we loved the outdoor area. Kitchen has everything we needed. The parking was plentiful.
Stayed 5 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The pictures do not do it justice! The screened in porch was so perfect for both eating and sitting in the very comfortable patio furniture. the fans made it super nice and we just watched the water, the boats and all the wildlife (a heron, an eagle, lots of cardinals, bunnies and more!!!). The master bedroom suite was just as in a 5 star hotel, and all other bedrooms very comfortable. The very modern kitchen had tons of spices, dry staples and all the gizmos anyone would need, with plenty of countertop space and a beautiful gas range. Sitting on the end of the pier for complete peace in the middle of nature was a terrific added bonus!!! We would definitely come again. (Beth was very responsive to all our questions, but we really didn't have any problems.)
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 June 2022
Thank you Daniel. I hope you had a good time at the wedding!
Verified review

10/10 Excellent

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 review

10/10 Excellent

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.
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