[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire apartment # Newly restored apartment in the heart of Chestertown Apartment in Chestertown with kitchen ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/fc8d3076.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Living area](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/038e56e6.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/c816d0fb.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Living area](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/ff521238.jpg?impolicy=resizecrop&rw=297&ra=fit) ![2 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/270b1239.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location In the heart of downtown Chestertown, this newly renovated apartment offers a unique blend of historic charm and modern comforts. With Evergrain Bakery across the street, enjoy fresh pastries and coffee while taking in the sights. The open living room/dining area/kitchen provides ample space to unwind after a day exploring Chestertown's offerings. 9.8 Exceptional ### Entire apartment 2 bedrooms1 bathroomSleeps 4 ## Popular amenities ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire apartment to yourself and will only share it with other guests in your party. ### Newly restored apartment in the heart of Chestertown Newly renovated apartment in downtown Chestertown. Directly across the street from Evergrain Bakery. In the center of all Chestertown has to offer. This apartment span the entire front of a recently restored building, built in 1877. Open living room/dining area/kitchen Historic character with all modem conveniences, including dishwasher, washer/dryer, TV with AppleTv and high speed wifi internet access. Off street parking for one car on first come first served basis with ample street parking. ## Property amenities ### Internet - Available in the apartment: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Microwave - Oven - Paper towels - Refrigerator - Spices - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 2 bedrooms - Bedsheets provided ### Bathroom - 1 bathroom - Hair dryer - Shampoo - Shower - Soap - Toilet paper - Towels provided ### Living spaces - Dining table - Living room ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk - Desk chair ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Safety features - Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector) - Smoke detector not reported (host has not indicated whether there is a smoke detector on the property) ## Similar properties ![Property grounds](https://images.trvl-media.com/lodging/119000000/118140000/118131300/118131300/w1075h1080x5y0-d2ed6db8.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access Chestertown - 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Within 2 Blocks of Fountain Park!! Chestertown - Washer - Dryer - Air conditioning [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-24&endDate=2025-10-25&selected=119124197&PinnedHotelID=119124197&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113590000/113586700/113586648/w1536h2048x598y0-f666fabb.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Grandma’s Cottage will wrap around you like a warm hug Betterton - Washer - Dryer - Air conditioning CA $314 CA $574 total includes taxes & fees Oct 11 - Oct 12 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-11&endDate=2025-10-12&selected=113586648&PinnedHotelID=113586648&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Minimum check-in age: 18 ### 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 ### Check-out instructions The host requires you complete the following before checking out: Remove personal items and remove leftover food and drinks Turn off the lights, lock the doors, and return the keys Failure to complete these may result in a negative review from the host. ### 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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip Host has not indicated whether there is a smoke detector on the property 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 Chestertown is home to this apartment. Historical Society of Kent County Maryland and Betterton Historic District are local landmarks, and the area's natural beauty can be seen at Chestertown Historic District and Wilmer Park. Crumpton Auction and Hazel Miner Monument are also worth visiting. [Visit our Chestertown travel guide](https://www.expedia.ca/Chestertown.dx7215) [View more Apartments in Chestertown](https://www.expedia.ca/Chestertown-Apartments.d7215-aaApartments.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%7C39.20838%2C-76.06502&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=c6ULtzXI0Z4W8n8rdV08wk0VA9c=) Chestertown, MD ### What's nearby - Historical Society of Kent County Maryland - 2 min walk - 0.2 km - Wilmer Park - 3 min walk - 0.3 km - River Arts Chestertown - 5 min walk - 0.4 km - Washington College - 12 min walk - 1.1 km - Rolphs Wharf Marina - 12 min drive - 9.0 km ### Getting around - Baltimore, MD (MTN-Martin State) - 105 min drive ### Restaurants - ‪McDonald's - ‬3 min drive - ‪Royal Farms - ‬5 min walk - ‪Dunkin - ‬2 min drive - ‪Procolino's - ‬3 min drive - ‪Subway - ‬2 min drive ## Frequently asked questions ### Is Newly restored apartment in the heart of Chestertown pet-friendly? > No, pets are not allowed at this property. ### What time is check-in at Newly restored apartment in the heart of Chestertown? > Check-in begins at 4:00 PM. ### What time is check-out at Newly restored apartment in the heart of Chestertown? > Check-out is at 11:00 AM. ### Where is Newly restored apartment in the heart of Chestertown located? > Situated in Chestertown, this apartment building is steps from Chestertown Historic District, Garfield Center for the Arts at the Prince Theater, and Historical Society of Kent County Maryland. Sumner Hall and Wilmer Park are also within 5 minutes. ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Newly restored apartment in the heart of Chestertown Reviews 9.8 ### 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 Cleanliness ### 10 Location 10 - Excellent 24 8 - Good 3 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 8/10 Good #### Russell C. Mar 2, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great location Nice downtown location. ##### Russell C. Stayed 2 nights in Feb 2025 ### 10/10 Excellent #### Karen G. Apr 29, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Excellent location right downtown! Great place / very spacious/ bed super comfy - kitchen has everything you need. Easy entry instructions - best location right downtown - near everything and an easy walk up to the college. Looking forward to staying here again! ##### Karen G. Stayed 2 nights in Apr 2025 ### 10/10 Excellent #### Verified traveller Sep 17, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stay Wonderful spot in the center of historical Chestertown, ##### Verified traveller Stayed 2 nights in Sep 2023 ### 10/10 Excellent #### Jeffrey W. May 2, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stay in Chestertown We had a great experience and stay in Chestertown. We stayed during Easter weekend so we could visit out son at Washington College. The apartment is in a great location. Our host was fantastic and very helpful. We will definitely be booking again next year. ##### Jeffrey W. Stayed 2 nights in Apr 2025 ### 10/10 Excellent #### Eliza M. May 15, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Far better than a hotel Booked this for a wedding since there were limited hotel options in town and everyone was jealous of our setup! Everything was spotless and the place is adorable. Worked out perfectly and you are walking distance from everything in town. Highly recommend! ##### Eliza M. Stayed 2 nights in May 2025 ### 10/10 Excellent #### April D. Mar 23, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Sparkling clean and great location We loved this apartment. The communication with the owner was very timely and clear! ##### April D. Stayed 2 nights in Mar 2025 ### 10/10 Excellent #### Betsy G. Jul 23, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great place The place was clean, well organized and decorated and a fantastic location. Would definitely go back again.! ##### Betsy G. Stayed 1 night in Jul 2023 ### 10/10 Excellent #### Tamara H. Apr 29, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Lovely Home The location was great. The decor was pretty and all very comfortable ##### Tamara H. Stayed 3 nights in Apr 2024 ### 8/10 Good #### Kathy and Rick R. May 30, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great place Very clean ##### Kathy and Rick R. Stayed 2 nights in May 2023 ### 10/10 Excellent #### Michael. T. Apr 3, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Excellent Location and Great Property! We stayed in this great apartment and found it to be in excellent condition and in a great location. Walking distance to all the shops, restaurants and bars Chestertown has to offer. The host was great to work with and we will be staying here again on our next trip to Chestertown! ##### Michael. T. Stayed 2 nights in Mar 2023 ### 10/10 Excellent #### Gary C. Feb 26, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Chesapeake Getaway This property, located in downtown Chestertown, provided a relaxing getaway for my wife and I to explore the quaint towns of the Chesapeake Bay region. We were able to explore the area, including a walk through Annapolis, starting and ending our day with Chestertown coffee and pastry shops, restaurants, and taverns. ##### Gary C. Stayed 2 nights in Feb 2024 ### 10/10 Excellent #### Erin D. Apr 23, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Washington College Sr. Weekend Best location to be in walking distance that all Chestertown has to offer. Property was clean and had all we needed and more. ##### Erin D. Stayed 2 nights in Apr 2023 ### 10/10 Excellent #### Katherine P. Nov 8, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfecton We fell in love with Chestertown and are so glad we stayed in the heart of downtown at this charming vrbo. Everything was perfect. Will return and recommend ##### Katherine P. Stayed 2 nights in Oct 2024 ### 10/10 Excellent #### Tara M. Feb 27, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Amazing Apartment I would stay there anytime. Apartment is clean and spacious. Convenient to center of town. Owner was easy and amazing to work with. 5 stars. ##### Tara M. Stayed 2 nights in Feb 2023 ### 10/10 Excellent #### Dan B. Aug 18, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Very nice Awesome ##### Dan B. Stayed 4 nights in Aug 2024 ### 10/10 Excellent #### Linda Carol K. Dec 30, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Convenient to everything. The location could not be better. I could walk anywhere in town. The space is large. The host was very easy to communicate with both before and during the stay. ##### Linda Carol K. Stayed 3 nights in Dec 2023 ### 10/10 Excellent #### Michelle K. May 12, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Regatta getaway This was a great apartment in an excellent location. We visited Washington college and attended a sailing regatta. The Evergrain Bakery across the street was amazing. Shops and restaurants all within walking distance! Apartment was well stocked, nicely decorated and clean! Also very close to the Hodson boathouse. It was a 3 minute drive! ##### Michelle K. Stayed 2 nights in May 2024 ### 10/10 Excellent #### Alison W. Oct 2, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect We came to Chestertown for a wedding and fell in love with this town and apartment. The apartment is perfectly located across from a bakery and next door to an incredible restaurant, the Kitchen. The apartment is so clean and perfectly comfortable for a family of 4. ##### Alison W. Stayed 2 nights in Sep 2023 ### 10/10 Excellent #### terry c. Mar 19, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Julie was great. Attentive and quick to respond. Very clean, well equipped apartment. Terrific. with the exception of the church clock chime..no fault of Julie. ##### terry c. Stayed 3 nights in Mar 2023 ### 10/10 Excellent #### Douglas G. May 27, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Memorial Weekend We stayed here for Memorial weekend and the location was perfect for watching the Tea Party Parade! The property is directly across the street from Evergrain which is perfect for coffee and baked goods. Shopping was within walking distance which was so convenient. Beds were very comfortable and the place was really clean. We will definitely stay here again! ##### Douglas G. Stayed 3 nights in May 2025 ### 10/10 Excellent #### Jacquelin N. W. Nov 22, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect ##### Jacquelin N. W. Stayed 4 nights in Oct 2024 ### 10/10 Excellent #### Sarah Jun 25, 2024 ##### Sarah Stayed 3 nights in Jun 2024 ### 8/10 Good #### Carlos C. Apr 5, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Good Location - Nice and Clean Located in the center of town, with easy access to Restaurants and the River. Easy to get in and out and parking available. ##### Carlos C. Stayed 2 nights in Mar 2024 ### 10/10 Excellent #### Mark C. Aug 25, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great Stay The unit was really nice and location was perfect. ##### Mark C. Stayed 2 nights in Aug 2023 ### 10/10 Excellent #### Deborah K. Jun 23, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Fabulous renovated apartment in prime location we loved the location and being able to walk to the shops and restaurants in Chestertown. ##### Deborah K. 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