[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Country Estate in Historic District Family-friendly vacation home in Chestertown ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/e626cb61.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Interior](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/1723fbc6.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior detail](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/cffe9d0c.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior detail](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/f72e2547.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/adbcc20f.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Historic Chestertown charm meets modern comfort at this beautiful home. Step into a first-floor bedroom with private bath, explore the secluded yard, and enjoy gas grilling on the patio. With comfortable beds and quality linens, well-equipped kitchen amenities await in this peaceful retreat. 10 Exceptional ### Entire home 5 bedrooms4 bathroomsSleeps 10 ## Popular amenities - - - Dryer - Washer - Fireplace - Barbecue grill ## 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. ### Country Estate in Historic District Enjoy historic ambiance with every modern convenience, including a first floor bedroom with private bath. Our house is in the historic district of Chestertown, and a two block walk from both Washington College and the Chestertown waterfront. It features two master bedroom suites, one on the ground floor. There are three more bedrooms and a secluded yard. Just outside your garden gate is over an acre of manicured gardens to explore. Gas grill on patio Over the years, we have stayed in a lot of vacation rentals, and we know what we need as guests. 1\. Comfortable beds and furniture 2\. Quality linens and towels 3\. Limitless hot water 4\. Well-equipped kitchen (hate buying corkscrews!) 5\. Peace and privacy, but security in knowing someone is always available. 6\. CLEAN, CLEAN, CLEAN. Our goal is to give you the experience we would want to have. To maintain quality control we do our own cleaning, and we are available 24/7 if you should need anything, but will be invisible otherwise. The entire house and fenced yard is yours, as well as the large gardens, which are right outside the back gate. We might be doing some gardening in the large garden, but will keep our distance. ## Property amenities ### Beach - Beach loungers - Beach towels ### Internet - Available in the house: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Blender - Coffee grinder - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Electric kettle - Ice maker - Kitchen island - Microwave - Oven - Paper towels - Refrigerator - Spices - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 5 bedrooms - Bedsheets provided ### Bathroom - 3.5 bathrooms - Hair dryer - Shampoo - Shower - Soap - Toilet paper - Towels provided ### Living spaces - Dining table - Fireplace - Living room ### Entertainment - Books - Games - Smart TV with cable/satellite channels - Stereo ### Outdoor areas - Balcony - Fenced yard - Firepit - Garden - Gas grill - Outdoor furniture ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk - Desk chair ### Comfort - Air conditioning - Heating ### Pets - Pet friendly ### Suitability/Accessibility - Smoking not allowed - Note from host: No smoking on property. ### Services and conveniences - Iron/ironing board ### Location highlights - In the city center ### 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) - First aid kit - Fire extinguisher - Deadbolt lock ### General - Garden ## Similar properties ![Exterior](https://images.trvl-media.com/lodging/35000000/34530000/34520600/34520502/fed476c4.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Waterfront Home,Private Dock,Bring Boat,Eastern shore, Betterton,Chestertown Worton - Kitchen - Washer - Dryer - Pet-friendly 9.8 Exceptional 94 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&selected=34520502&PinnedHotelID=34520502&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/e3526265.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Circa 1900 Home in the Heart of Historic Downtown Chestertown Chestertown - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 75 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&selected=66473084&PinnedHotelID=66473084&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/65000000/65000000/64994000/64993941/e6a8684a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! 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Close to the Beach Betterton - Kitchen - Washer - Dryer - Pet-friendly 9.6 Exceptional 45 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&selected=74897548&PinnedHotelID=74897548&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83930000/83926700/83926700/d1ca16e3.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Historic Downtown Garden Oasis with Private Patio Chestertown - Kitchen - Free WiFi - Air conditioning - Outdoor space 10 Exceptional 40 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&selected=83926700&PinnedHotelID=83926700&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/39c19e25.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town Chestertown - Breakfast included - Kitchen - Washer - Dryer 9.8 Exceptional 84 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&selected=18994126&PinnedHotelID=18994126&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/118000000/117470000/117463700/117463692/4d322b5b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Eastern shore beachfront cottage with stunning sunset views! Worton - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 2 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&selected=117463692&PinnedHotelID=117463692&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/114000000/113420000/113417900/113417810/1d961d4b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm! Chestertown - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 10 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&selected=113417810&PinnedHotelID=113417810&HadPinnedHotel=true®ionId=-1&adults=2) ![Dining](https://images.trvl-media.com/lodging/109000000/108600000/108596300/108596202/44a02bd7.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets Rock Hall - Kitchen - Dryer - Pet-friendly - Air conditioning 10 Exceptional 8 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&selected=108596202&PinnedHotelID=108596202&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Contactless check-in available Minimum check-in age: 25 ### 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 allowed Service animals are welcome, and are exempt from fees Restrictions apply; for more information contact the property at the number on the booking confirmation Note from host: One time $20 pet fee ### Children and extra beds Children are welcome ### Events No events allowed No parties. ### Smoking Smoking is not permitted No smoking on property. ## 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 Note from host: No parties. 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, a first aid kit, and a deadbolt lock 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 ### Property is also known as Estate In Historic District Country Estate in Historic District Chestertown Country Estate in Historic District Private vacation home ## 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%7C39.21173%2C-76.06716&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=NfEuNT1VqcC_GG0OchD0ynyizwE=) Chestertown, MD #### What's nearby - River Arts Chestertown - 5 min walk - 0.4 km - Historical Society of Kent County Maryland - 8 min walk - 0.7 km - Washington College - 8 min walk - 0.7 km - Wilmer Park - 9 min walk - 0.8 km - Rolphs Wharf Marina - 12 min drive - 9.4 km #### Getting around - Baltimore, MD (MTN-Martin State) - 105 min drive #### Restaurants - ‪Royal Farms - ‬5 min walk - ‪McDonald's - ‬3 min drive - ‪Dunkin - ‬2 min drive - ‪Procolino's - ‬3 min drive - ‪Subway - ‬18 min walk ## Frequently asked questions ### Is Country Estate in Historic District pet-friendly? > Yes, pets are allowed at this property. Some restrictions may apply, so please contact the property for more details. ### What time is check-in at Country Estate in Historic District? > Check-in begins at 4:00 PM. ### What time is check-out at Country Estate in Historic District? > Check-out is at 11:00 AM. ### Where is Country Estate in Historic District located? > Located in the center of Chestertown, this family-friendly vacation home is within a 10-minute walk of Garfield Center for the Arts at the Prince Theater, Chestertown Historic District, and Wilmer Park. Historical Society of Kent County Maryland and Sumner Hall 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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