Title: Circa 1900 Home in the Heart of Historic Downtown Chestertown Reviews, Deals & Photos 2026 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/Hotel-Search?regionId=&selected=66473084&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Circa 1900 Home in the Heart of Historic Downtown Chestertown ## Photo gallery for Circa 1900 Home in the Heart of Historic Downtown Chestertown ![4 bedrooms, desk, iron/ironing board, free WiFi - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/716726a6.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Interior - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/0a73a6e9.jpg?impolicy=resizecrop&rw=297&ra=fit) ![TV, books - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/72f4694e.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/4e7c5213.jpg?impolicy=resizecrop&rw=297&ra=fit) ![TV, books - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/002c716d.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. ## Reviews 10 Exceptional ### Entire home 4 bedrooms2 bathroomsSleeps 6 ## Popular amenities - Kitchen - Washing machine - Dryer - Free Wi-Fi - Air-conditioning - 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 transport - Parking on site ### Kitchen - Blender - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Electric kettle - Hob - Ice maker - Microwave - Oven - Paper towels - Refrigerator - 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 - Smoke-free property ### Services and conveniences - Iron/ironing board ### Location highlights - In a village - In the city centre - 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 ![Free daily full breakfast ](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown Chestertown - Pool - Breakfast included - Pet-friendly - Parking included 8.6 Excellent 879 reviews £83 includes taxes & fees 8 Mar - 9 Mar [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-08&endDate=2026-03-09&selected=1700736&PinnedHotelID=1700736&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-03-13&endDate=2026-03-14&selected=66473084&PinnedHotelID=66473084&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=66473084,1700736) ## 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 Information provided by the property may be translated using automated translation tools ### 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 This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking. 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 On-site parties or group events are strictly prohibited Host has indicated that there is a carbon monoxide detector on the property Host has indicated that 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 holiday home is in the city centre. 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. Take the opportunity to explore the area for water adventures such as fishing and other activities like birdwatching. [Visit our Chestertown travel guide](https://www.expedia.co.uk/Chestertown.dx7215) [View more Holiday homes in Chestertown](https://www.expedia.co.uk/Chestertown-Private-Holiday-Homes.d7215-aaPrivateHolidayHomes.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 - ![Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.](https://images.trvl-media.com/place/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Washington College 8 min walk \- 0.4 miles - Historical Society of Kent County Maryland 2 min walk \- 0.1 miles - Garfield Center for the Arts at the Prince Theater 3 min walk \- 0.2 miles - Wilmer Park 6 min walk \- 0.4 miles - River Arts Chestertown 6 min walk \- 0.4 miles ### Getting around - Baltimore, MD (MTN-Martin State) 104 min drive ### Restaurants - Milano's Pizzeria 4 min drive - Royal Farms 4 min drive - Dunkin 2 min drive - McDonald's 4 min drive - Royal Farms 3 min walk ## Frequently asked questions ### Is Circa 1900 Home in the Heart of Historic Downtown Chestertown pet-friendly? ### How much is parking at Circa 1900 Home in the Heart of Historic Downtown Chestertown? ### What time is check-in at Circa 1900 Home in the Heart of Historic Downtown Chestertown? ### What time is check-out at Circa 1900 Home in the Heart of Historic Downtown Chestertown? ### Where is Circa 1900 Home in the Heart of Historic Downtown Chestertown located? ## 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 ## Reviews ### 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.co.uk/lp/b/content-guidelines) 10 - Excellent 79 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 10 Location ## Reviews ### 10/10 Excellent #### Darren H. 19 Oct 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy We love the location which is just steps away from the High Street. Very comfortable beds and very thoughtfully equipped. ##### Darren H. Stayed 3 nights in Oct 2025 ### 10/10 Excellent #### Maya L. 12 Oct 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy This lovely home was adorable! Very clean and cozy. A very comfortable space. It was also in a great location. Only a five minute walk to the Main Street. We went to the farmer’s market Saturday morning and a cute cafe for breakfast. Would definitely stay here again. ##### Maya L. Stayed 2 nights in Oct 2025 ### 10/10 Excellent #### Mary D. 25 Aug 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 #### Tricia L., Washington, DC, USA 8 Aug 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 #### Bethany M. 6 Apr 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Well decorated comfortable home in a great location The home is on a beautiful street in downtown Chestertown that is walkable to restaurants, stores, and the Saturdays farmers market. Each room is well decorated and stocked for a comfortable stay. We enjoyed the backyard with spring flowers in bloom. We would highly recommend this home! ##### Bethany M. Stayed 2 nights in Apr 2025 ### 10/10 Excellent #### Nicole N. 20 Mar 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 #### Christopher P. 29 Dec 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 18 Sept 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 #### Sallie S. 19 Dec 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 #### chris r. 2 Oct 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. 31 Jul 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 #### Diane P. 12 May 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Lovely getaway This is a lovely home on a beautiful garden lined street. We were within walking distance of restaurants, coffee shops and even Chestertown’s Saturday morning market. The home is well maintained and appointed with thoughtful touches that made our stay relaxing and enjoyable. My husband and I will be staying here again. ##### Diane P. Stayed 3 nights in May 2024 ### 10/10 Excellent #### amy p. 24 Jan 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 #### Marcella M. 10 Jun 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Wonderful home in Chestertown We rented four bedroom home in Chestertown for graduation weekend. Home has everything you could possibly need. All bedrooms are upstairs with one bathroom and one bathroom on lower level. If you have any elderly members of your party, this may be ##### Marcella M. Stayed 3 nights in May 2025 ### 10/10 Excellent #### Pam S. 6 Dec 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 #### Terrie S. 6 Nov 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. 7 Jul 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 #### susan s. 24 Nov 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Everything was great. Beds were very comfortable and the location was great. ##### susan s. Stayed 3 nights in Nov 2025 ### 10/10 Excellent #### Michael H. 24 Sept 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Great Location and nice house! ##### Michael H. Stayed 3 nights in Sep 2025 ### 10/10 Excellent #### Gary N. 8 Jun 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 #### Deborah K. 27 Mar 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 #### Lora D. 15 Aug 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy The house is exactly as advertised. It is well stocked and it’s clear the host has put a lot of thought into making the house comfortable for folks. Host was also very quick to respond. Chestertown is lovely and this house is in the perfect location. Will stay here again! ##### Lora D. Stayed 4 nights in Aug 2025 ### 10/10 Excellent #### Darren H. 31 Oct 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 #### Chris C. 6 Jul 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 #### David F. 5 Nov 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 ---