Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

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.

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!

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

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.

Beautiful home with full amenities and wonderful view of the Chester River .

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.

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.

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.

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!

Beautiful views of the water. Amazing brand new hot tub. Very spacious layout of the house.

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!

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.

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.

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.

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

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.

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!

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!

We have stayed at various places in this area over the years and this one checked all the boxes.

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!

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!

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.