[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Circa 1900 Home in the Heart of Historic Downtown Chestertown Vacation home in Chestertown with kitchen and patio ![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/e3526265.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Dining](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/c370010d.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/6f840824.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/4e7c5213.jpg?impolicy=resizecrop&rw=297&ra=fit) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/f3c5c074.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location On a picturesque one-way street lined with historic homes, this 1900-built house combines old-world charm with modern comforts. Stroll to the Chester River Waterfront, Saturday farmers market, and Chestertown Marina or enjoy free on-street parking outside your doorstep. 10 Exceptional ### Entire home 4 bedrooms2 bathroomsSleeps 6 ## Popular amenities - Dryer - Washer - Parking available - Barbecue grill - Kitchen - Outdoor space ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Circa 1900 Home in the Heart of Historic Downtown Chestertown Beautiful1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic Chestertown has to offer as the house is walking distance to the shops, restaurants, Chester River Waterfront, and year round Saturday farmers market. Located on a one way street that is flanked with beautiful historic homes and free on street parking. For those with boats, the home is a short walk to the Chestertown Marina which has a boat ramp and transient slips. Our home is only 2.6 miles from Brittland Manor. Please note there is a ring camera by the front door for security purposes. ## Property amenities ### Internet - Available in the house: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Blender - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Electric kettle - Ice maker - Microwave - Oven - Paper towels - Refrigerator - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 4 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Bathtub or shower - Hair dryer - Shampoo - Shower - Soap - Toilet paper - Towels provided ### Living spaces - Dining table - Living room ### Entertainment - Books - Games - TV ### Outdoor areas - Barbecue grill - Fenced yard - Firepit - Garden - Outdoor furniture - Patio ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk - Desk chair ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - In a village - In the city center - Near a health/beauty spa - Near a hospital - Near the marina ### Things to do - Birdwatching nearby - Fishing nearby ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) - Fire extinguisher ### General - Garden ## Similar properties ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/fc8d3076.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Newly restored apartment in the heart of Chestertown Chestertown - Kitchen - Washer - Dryer - Free WiFi 9.8 Exceptional 27 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-20&endDate=2025-10-21&selected=90876079&PinnedHotelID=90876079&HadPinnedHotel=true®ionId=-1&adults=2) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119130000/119124200/119124197/a6438229.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!! 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Worton - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 2 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-20&endDate=2025-10-21&selected=117463692&PinnedHotelID=117463692&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor dining](https://images.trvl-media.com/lodging/95000000/94050000/94049900/94049847/adb85d45.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Lovely 2 bedroom and loft apartment with AC, WiFi overlooking the Chester River Chestertown - Kitchen - Air conditioning - Outdoor space - Parking available [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-20&endDate=2025-10-21&selected=94049847&PinnedHotelID=94049847&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/6b42c6a9.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Waterfront Retreat with Private Dock and Beach Worton - Kitchen - Free WiFi - Air conditioning - Parking available 10 Exceptional 24 reviews CA $244 CA $434 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-07&endDate=2025-10-08&selected=103180013&PinnedHotelID=103180013&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/102000000/101992100/101992099/w507h683x259y0-6d253ed0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest Chestertown - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 17 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-20&endDate=2025-10-21&selected=101992099&PinnedHotelID=101992099&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 3:00 PM Minimum check-in age: 21 ### Check-out Check-out before 11:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Pets Pets not allowed ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## 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 Onsite parties or group events are strictly prohibited Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ## About the area Located in Chestertown, this vacation home is in the city center. 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. Take an opportunity to explore the area for water adventures such as fishing and other activities like birdwatching. [Visit our Chestertown travel guide](https://www.expedia.ca/Chestertown.dx7215) [View more Vacation homes in Chestertown](https://www.expedia.ca/Chestertown-Private-Vacation-Homes.d7215-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C39.20909%2C-76.06378&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=9Qr7AnRxWV3T6TTJwvOUps9hlT8=) Chestertown, MD ### What's nearby - Historical Society of Kent County Maryland - 2 min walk - 0.2 km - Wilmer Park - 6 min walk - 0.6 km - River Arts Chestertown - 6 min walk - 0.6 km - Washington College - 11 min walk - 1.0 km - Rolphs Wharf Marina - 12 min drive - 9.0 km ### Getting around - Baltimore, MD (MTN-Martin State) - 104 min drive ### Restaurants - ‪McDonald's - ‬4 min drive - ‪Royal Farms - ‬3 min walk - ‪Dunkin - ‬2 min drive - ‪Procolino's - ‬3 min drive - ‪Subway - ‬2 min drive ## Frequently asked questions ### Is Circa 1900 Home in the Heart of Historic Downtown Chestertown pet-friendly? > No, pets are not allowed at this property. ### What time is check-in at Circa 1900 Home in the Heart of Historic Downtown Chestertown? > Check-in begins at 3:00 PM. ### What time is check-out at Circa 1900 Home in the Heart of Historic Downtown Chestertown? > Check-out is at 11:00 AM. ### Where is Circa 1900 Home in the Heart of Historic Downtown Chestertown located? > Located in the heart of Chestertown, this vacation home is steps from Historical Society of Kent County Maryland, Chestertown Historic District, and Garfield Center for the Arts at the Prince Theater. Sumner Hall and River Arts Chestertown are also within 10 minutes. ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Circa 1900 Home in the Heart of Historic Downtown Chestertown Reviews 10 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 74 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10/10 Cleanliness ### 10/10 Excellent #### Gary N. Jun 8, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Great house, will stay again in the future. ##### Gary N. Stayed 3 nights in Jun 2025 ### 10/10 Excellent #### Chris C. Jul 6, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great location, very comfy house Lovely restored home on a very nice street in the heart of Chestertown. Comfy beds, loved the front porch. Cool coffee station! We had everything we needed, we really enjoyed our week's stay. Thank you to the owner for responding so promptly and resolving the problem with one of the shower faucets, really appreciated that. ##### Chris C. Stayed 7 nights in Jun 2025 ### 10/10 Excellent #### Deborah K. Mar 27, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautifully renovated historic property on quiet street, walking distance to shops and restaurants We had a wonderful stay at this property! ##### Deborah K. Stayed 2 nights in Mar 2023 ### 10/10 Excellent #### Vijay S. Jun 13, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Property was as described in the listing!! Very clean and well appointed with toiletries, towels, dishes, etc.Very clean, safe, quiet neighborhood.Enjoyed walking to the farmer's market, Evergrain Bread Company, and waterfront area.I would highly recommend if you're able to navigate the stairs! ##### Vijay S. Stayed 3 nights in May 2025 ### 10/10 Excellent #### Mary D. Aug 25, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Small town trip. Enjoyed the stay and house very comfortable. ##### Mary D. Stayed 5 nights in Aug 2024 ### 10/10 Excellent #### Nicole N. Mar 20, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Chestertown House was in a great location and very well appointed. We had everything we needed. Would highly recommend. ##### Nicole N. Stayed 3 nights in Mar 2025 ### 10/10 Excellent #### Darren H. Oct 31, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Fall weekend Lovely, well kept and tastefully furnished house in a great location. ##### Darren H. Stayed 2 nights in Oct 2024 ### 10/10 Excellent #### Sallie S. Dec 19, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Girls Trip Great space. Cozy fireplace. Well appointed house. Perfect location, we walked everywhere. ##### Sallie S. Stayed 2 nights in Dec 2024 ### 10/10 Excellent #### David F. Nov 5, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Downrigging Festival We enjoyed everything about the property. ##### David F. Stayed 4 nights in Oct 2024 ### 10/10 Excellent #### Tricia L., Washington, DC, USA Aug 8, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Everything you could need in perfect location The property is charming, clean, well-equipped, and located steps to the farmers' market and downtown shops. We would definitely stay again. ##### Tricia L. Stayed 3 nights in Aug 2023 ### 10/10 Excellent #### Christopher P. Dec 29, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Go-To Place in Chestertown We've stayed here twice now and always enjoy it. It's very comfortable and is near everything. Will definitely return. ##### Christopher P. Stayed 7 nights in Dec 2023 ### 10/10 Excellent #### Verified traveller Sep 18, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect Great house, location and host! ##### Verified traveller Stayed 3 nights in Sep 2023 ### 10/10 Excellent #### James T. Jul 10, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great Stay for Summer Weekend in Chestertown Michelle's home was perfect for our group (two couples with kids) to stay for a weekend in Chestertown attending a wedding. Home was clean and well appointed for our stay, right downtown for easy walking distance to food and shopping options. Would definitely stay here again during another trip to the area, thank you! ##### James T. Stayed 3 nights in Jul 2022 ### 10/10 Excellent #### amy p. Jan 24, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect! This is the cutest place! Super clean and equipped to the max, everything we could possibly need was provided. The beds/linens are extremely comfortable. And our hostess was quick to respond to a problem with the heat. Highly recommend! ##### amy p. Stayed 4 nights in Jan 2025 ### 10/10 Excellent #### Cheryl S. Jul 14, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Felt Like Home The property was exactly as described and felt like home, and property manager was gracious and accommodating. The amenities were thoughtfully selected and appreciated. I will definitely stay here when I return to the area. ##### Cheryl S. Stayed 5 nights in Jul 2023 ### 10/10 Excellent #### chris r. Oct 2, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great spot Great spot and location! Everything we needed was already there. Thank you! ##### chris r. Stayed 4 nights in Sep 2023 ### 10/10 Excellent #### Arianna G. Jul 31, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Fabulous Chestertown What a wonderful vrbo. Centrally located, charming historic home that was renovated. Really felt like “home”. So much so that the family decided that we’d like to make it an annual tradition ##### Arianna G. Stayed 7 nights in Jul 2023 ### 10/10 Excellent #### Nina V., Libertyville, Illinois Jan 9, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Charming home in walk to town location! Our family loved staying in this charming home in a perfect location to enjoy Chestertown! We walked to restaurants and shops and never needed to drive during our stay. We appreciated the wine, treats, coffee ,and other amenities the host had available for us . If we travel to Chestertown again we would love to book another stay. ##### Nina V. Stayed 3 nights in Dec 2022 ### 10/10 Excellent #### Pam S. Dec 6, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Girls weekend Michelle was absolutely wonderful to deal with, and her place is just lovely. It was spotless when we arrived and had absolutely everything we needed for a comfortable weekend. The location is great. We will be back. ##### Pam S. Stayed 4 nights in Nov 2023 ### 10/10 Excellent #### Missy P. May 26, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Lucky to be first renter of home! We were lucky enough to be the first renter of this home after its complete renovation. Tastefully decorated and relaxing accommodations. Well stocked kitchen and bathroom necessities. Nice for a family of 6 to explore Chestertown. ##### Missy P. Stayed 2 nights in May 2021 ### 10/10 Excellent #### Naked S. Jan 29, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Chestertown Well appointed, everything you could want was there. Wish there had been regular cable however. ##### Naked S. Stayed 2 nights in Jan 2023 ### 10/10 Excellent #### Terrie S. Nov 6, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Charming Visit My 3 friends and I thoroughly enjoyed our stay. We loved the house and felt totally comfortable. We enjoyed walking downtown and taking in the colors, sounds, food and people at the Farmers Market. Hopefully, my granddaughter will continue to attend WAC to give me a good reason to visit often. I will return to Queen St. ##### Terrie S. Stayed 2 nights in Nov 2023 ### 10/10 Excellent #### Suzi A. Jul 7, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### A week in living history -Chestertown, Ms The house we rented resided on Queen Street, an historical street near the Chester River. It provided our family with welcoming spaces to chat, dine and watch shows as well as four comfortable bedrooms to sleep peacefully at night. We walked to nearby shops and a farmer market, all charming. The people are friendly and helpful. One senses a true feeling of commnity! We will return for another vacation in this lovely town well preserved and charming! ##### Suzi A. Stayed 7 nights in Jun 2024 ### 10/10 Excellent #### Alisa R. Jul 22, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Enjoyed this updated home This home was nicely decorated with everything well thought out by the owner. Well appointed and clean design aesthetic. Loved the walk in closet; don’t even have that at home. Great to be able to walk to the small downtown area. Very welcoming. Would definitely rent again. ##### Alisa R. Stayed 6 nights in Jul 2023 ### 10/10 Excellent #### Nora M. Jul 5, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect! We stayed a week at this fantastic house. Everything needed was provided. The host was available if needed (we didn’t - she had thought of everything). The house is spacious and clean, and walking distance to so many good restaurants, cafes, a theater, and so much more. We were sad to leave and hope to be back. ##### Nora M. 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