Title: Circa 1900 Home in the Heart of Historic Downtown Chestertown - Latest Reviews, Deals & Photos 2025 - Expedia.ca [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) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/6f840824.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) ![Dining](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/c370010d.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) - Overview - Location - Amenities - Policies 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 ![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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Pet friendly cabin at waterfront farm! Chestertown - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 10 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-05&endDate=2025-12-06&selected=113417810&PinnedHotelID=113417810&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/04bd524d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### First Floor Studio Apartment in Historic Chestertown Chestertown - Pool - Hot tub - Washer - Dryer 9.6 Exceptional 106 reviews CA $139 CA $223 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-25&endDate=2025-11-26&selected=75854900&PinnedHotelID=75854900&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/63000000/62980000/62979100/62979011/fa04023d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful, spacious waterfront home, an easy walk to historic Chestertown Chestertown - Kitchen - Washer - Dryer - Air conditioning 9.8 Exceptional 23 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-05&endDate=2025-12-06&selected=62979011&PinnedHotelID=62979011&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 ![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 - Chestertown Historic District - 3 min walk - 0.3 km - Wilmer Park - 6 min walk - 0.6 km - River Arts Chestertown - 6 min walk - 0.6 km - Washington College - 8 min walk - 0.7 km #### Getting around - Baltimore, MD (MTN-Martin State) - 104 min drive #### Restaurants - ‪Royal Farms - ‬3 min walk - ‪McDonald's - ‬4 min drive - ‪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. ### How much is parking? > Onsite parking is available at the 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. 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