Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
House in Chestertown, MD
8 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
Includes essentialsGarden, Kitchen or Kitchenette, Air conditioner and more
About this house rental
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.
Amenities
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
Hot tub or spa
TV
Garden
Family friendly
Map of Chestertown, MD
$$$$
Ratings and reviews
4.0 / 5.0
The property was very nice. Perfect for our group attending a wedding.
5.0 / 5.0
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.
5.0 / 5.0
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!
5.0 / 5.0
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!
5.0 / 5.0
We have stayed at various places in this area over the years and this one checked all the boxes.
5.0 / 5.0
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!
5.0 / 5.0
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!
5.0 / 5.0
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.
5.0 / 5.0
This house is a gem! The property is fantastic, with such a beautiful backyard.
5.0 / 5.0
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.
5.0 / 5.0
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!
5.0 / 5.0
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.
5.0 / 5.0
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!
5.0 / 5.0
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.
5.0 / 5.0
We had ANOTHER great stay at your place on the river. Thanks, Beth
5.0 / 5.0
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!
5.0 / 5.0
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.
5.0 / 5.0
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.
5.0 / 5.0
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!
4.0 / 5.0
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.
5.0 / 5.0
Great
5.0 / 5.0
We had fun on our visit to Chestertown. It's a great colonial-style town, with nice restaurants and coffee shops.
We enjoyed the property's hot tub with its view of the river. And we took several canoe rides along the river, too. It was easy to launch the canoe from the sandy beach.
The house was great! Comfortable beds, modern kitchen, lots of sofas for relaxing. A very satisfying visit!
5.0 / 5.0
We booked this property for our family to stay during my cousins wedding weekend. We selected it based on the single level and low step count for my grandmother who was planning on staying with us, but unfortunately had a stroke and was not able to make it. It is the perfect location on the river, close to town, and filled with amenities. While in late dec it was way too cold to use the paddleboards, I’m sure those would be lovely in the warmer months. We loved the fireplace and that the kitchen had everything needed to make breakfast during our stay. The beds were all very comfortable, which is rare for a rental. The heated floor in the master bathroom was a nice surprise as well. The property was difficult to find at night due to lack of lighting , but we did just fine with our GPS. Beth was kind enough to let us know that the property was available early on check in day, which saved us from a meltdown with our 7 and 1 year olds who were worn out from our day in the car. My only struggle was that the cabinets were not childproof, which was a struggle with a toddler but nothing unexpected. If we had brought my grandmother, should would have struggled as the toilet area in the master doesn’t have grab bars and the master bed would have been difficult to get in and out of due to its height, maybe something to consider for the future as this is a property with the ability to be handicap accessible. We loved the house and would definitely stay again.
5.0 / 5.0
My friends and I had a great weekend in Maryland. Our stay at the Connor’s house was the perfect place to get away, relax and enjoy. It was our hub for the days in which we attended both University of Maryland and Baltimore Ravens football games. Both locations around an hour away.
The house itself is spacious, clean and comfortable. We spent the majority of our time lounging by the fireplace. The property is beautiful with a large yard and scenic view of Chesapeake Bay. We were visited by a couple bald eagles each morning. If not for the chill in the air, we would have spent much more time outside or in the water.
The rental experience with Beth was a pleasure. She made us feel at home. Hopefully, we’ll make our way back soon.
5.0 / 5.0
Good,
A few minor repairs should be done master bath one hot water did not work,
other bath wash bowl stopper did not work
third bath has a water drip needs repaired
5.0 / 5.0
This was our third time staying in this beautiful home. The home has everything you need to have a great time. We saw eagles, caught a few crabs and catfish from the pier . The owner Beth is quick to respond for anything you need. Hope to book it again next year.
2.5 / 5.0
Great place for our family stay. Beautiful sunsets, loads of fun on the river, and a responsive owner!! Thanks, Beth!
5.0 / 5.0
We had a lovely time in this home - playing cards in screened in patio, paddleboarding, and exploring the little towns around the bay. The homeowner, Beth, was made everything very easy and was a pleasure to work with for the rental.
5.0 / 5.0
Great gathering place for our mother’s 100th birthday celebration.
5.0 / 5.0
Our group of 8 adults enjoyed our stay. We enjoyed the water front seating, screened porch seating and interior spaces. Nice home!
5.0 / 5.0
Cozy home with spectacular views in a very convenient location. Excellent all around.
We stayed in Beth's home the week before our daughter's wedding at Brittland Manor, and it was one of the best decisions. We were able to relax together as a family, while also finalizing details for the wedding weekend. We loved the layout with the king master suite at the opposite end of the house from the other guest bedrooms. The kitchen was stocked as if you truly are staying in a home - there are spices, oils, coffee filters and wide variety of cooking utensils. The beds were comfy, and the house well-appointed and very clean, but the views of the Chester River from the back screened porch, yard and bedrooms really stole the show. Our family shared some wonderful evenings together around the fire pit and hanging out in the hammock. We won't forget this week. Beth was very quick to respond to questions and was very helpful. Check in was quite easy. We loved our stay here - it was so relaxing even during what could have been a stressful time. Tip: if you rent before a wedding, try to arrange check-out, as we did, for the day after the wedding venue checkout. We needed the extra day to pull ourselves together and decompress and re-pack. I would definitely stay here again.
5.0 / 5.0
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!!
5.0 / 5.0
Wonderful stay, even better than description
We had a wonderful experience. Beth made sure we had any questions answered. The house is bigger than what the pictures show and it's very well equipped.
5.0 / 5.0
Family Weekend
We LOVED Beth’s house!!!! It was absolutely beautifully furnished and the beds were so comfy! The property was gorgeous and so great to be right on the river with kayaks and canoes provided!! We loved hanging out in the screened in porch and highly recommend this property!!
5.0 / 5.0
Beautiful Sept. Weekend
Beautiful home and yard only added to our wondeful weekend celebrating our dear friends sons wedding. Gorgeous waterfront views, spacious floorplan. Everything we were looking for...plus🤗
5.0 / 5.0
Another wonderful trip
This is the third year that we have stayed in this beautiful home. Beth, the owner is very assessable if needed. The home is beautiful, clean and fully stocked. We spent our week crabbing and fishing from the pier, sitting by the fire pit and just relaxing. We will be back in 2022.. thanks again Beth !
5.0 / 5.0
Fantastic stay on the river
We stayed at this property during our daughters wedding at Brittland Manor, which was only 1.2 miles from the venue. The cleaning team prior to our arrival was fantastic… They even wash the inside and the outside of the windows!. It is equipped with very nice appliances, silverware, glassware and everything you could want. The furniture was beautiful and comfortable, linens and towels very upscale. Although we didn’t get to spend much time out front by the river, it was gorgeous. We would love to come back during a less stressful time and be able to take advantage of being right on the water and use the multiple water toys available to us. Beth was very communicative and helpful. It is very friend/family friendly with a gigantic screened porch. Great stay!!
5.0 / 5.0
Another wonderful vacation!
We had a wonderful family vacation at this comfortable home on the Chester River—again! We’ve been coming for a few years now and each time we find the home a terrific way to relax, enjoy the river, and spend time together. Beth is quick to respond to inquiries! Thanks for a great stay.
5.0 / 5.0
Great waterfront house!
We stayed 2 nights. Nice and clean house. Great location also. Easy communication with owner. Definitely come back later.
5.0 / 5.0
Lovely spot!
Beautiful home on the water. Great family vacation spot!
FAQs
How much does this house cost compared to others in Chestertown?
The average price for a rental in Chestertown is $183 per night. This rental is $272 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown?
We found 12 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, fireplace, and parking.
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