Title: Country Estate in Historic District - 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 # 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) ![Exterior detail](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/cffe9d0c.jpg?impolicy=resizecrop&rw=297&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/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 ![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 76 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-19&endDate=2025-11-20&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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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 - 10 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. Ask a question ## Country Estate in Historic District 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 Cleanliness ### 10 Location 10 - Excellent 70 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10/10 Excellent #### Chris W. Oct 15, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stay! Great stay! ##### Chris W. Stayed 2 nights in Oct 2023 ### 10/10 Excellent #### ira d. Jul 6, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### anniversary get away Lovely property, a nice anniversary get away for us. Thank you for the generosity and kindness to our hosts Beth and Bob. ##### ira d. Stayed 2 nights in Jul 2024 ### 10/10 Excellent #### Stephen C. Nov 11, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Excellent The home is beautiful! Beth and Bob took great care of us. I look forward to staying there again! ##### Stephen C. Stayed 2 nights in Nov 2023 ### 10/10 Excellent #### Mary S., Alexandria, Virginia Apr 1, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Gorgeous historic home; perfect location Beautiful renovation of historic home with spacious kitchen and four lovely bedrooms. One block from restaurants/spas etc but on quiet side street with charming large garden. Gracious host; well stocked home. A great find! ##### Mary S. Stayed 3 nights in Mar 2023 ### 10/10 Excellent #### Dominick B. Aug 27, 2020 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautiful house and property! We absolutely loved our stay here. The owners put a lot of effort and love into this property. Very beautiful and clean! They supply everything you need and more. Nice little town as well, right near the river and only a short trip to the beaches. We hope to return next summer and can’t wait to stay here again! Thank you! ##### Dominick B. Stayed 1 night in Aug 2020 ### 10/10 Excellent #### Diana M. Oct 20, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### WHAT A JEWEL Wow! This house is beautiful. A gem of old and new areas with lovely finishes and lots of space, each of us four guests had our own bedroom. The owners have supplied this domicile with every amenity one could imagine. It was well stocked with towels, paper products, kitchen tools and wonderful appliances. On the island stood a welcoming bottle of wine. Having enjoyed our stay so much, We may be returning next year! ##### Diana M. Stayed 3 nights in Oct 2024 ### 10/10 Excellent #### Stacy S. Mar 15, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Charming home in a charming town! This house is fantastic! From the tasteful decor to the radiant heated floors, it was a pleasure staying here. Wonderful fully appointed kitchen we actually could cook in, and very comfy beds and pillows! Hosts responded quickly to get a little wi-if issue resolved within 10 minutes! Can’t say enough good things about how great it is. We are returning and even extended our stay to enjoy the house again and the beautiful outside spaces! ##### Stacy S. Stayed 2 nights in Mar 2023 ### 10/10 Excellent #### Alisa R. Jul 31, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Owner wonderful to work with; walk to downtown Chestertown. VRBO screwed up our booking and the owner took great pains to help us rebook a different property that they own in the neighborhood. She went above and beyond to make sure that our vacation went smoothly and communicated well with us every step of the way. What could have been an awful experience turned out to be a wonderful one. We had a great vacation. Head's up to other customers out there: VRBO has messed up 3 of our bookings this past 12 months. Make sure you DM the owner to ensure that everything is done correctly. ##### Alisa R. Stayed 6 nights in Jul 2024 ### 10/10 Excellent #### Kyle W. Jan 20, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Exemplary! Everything about this property is perfection. It’s like walking into a brand new 1920s house. The charm is all there in spades, but the woodwork and hardware are in mint condition throughout. It’s the most perfectly kept old house I’ve ever stayed in. All that, but there are modern touches, too. The kitchen is huge and well stocked, and the main bath has a huge jacuzzi tub. Our dog had a blast running around the large park-like yard. The house is close to everything in town. The hosts were quick to respond. It was just a fantastic visit in every way. We hope to come back with friends soon! ##### Kyle W. Stayed 2 nights in Jan 2023 ### 10/10 Excellent #### Robin G. Jun 15, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Great hosts, location, gardens, and overallstay! ##### Robin G. Stayed 2 nights in Jun 2025 ### 10/10 Excellent #### Gwen R. Jun 11, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Everything was wonderful! Thank you! ##### Gwen R. Stayed 2 nights in May 2025 ### 10/10 Excellent #### Elder p. May 4, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Wedding Weekend Beautiful kitchen so whole family could cook dinner together Friday night before soiree at Brittland Manor. Patio out back, perfect for sipping coffee and chatting. Close to town, lots of places to walk to - including farmer's market and the college. ##### Elder p. Stayed 2 nights in May 2025 ### 10/10 Excellent #### Michael D. Mar 2, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Chestertown wedding Place is FABULOUS!!! Fantastic location easy to walk around town. THANKS FOR EVERYTHING ##### Michael D. Stayed 3 nights in Feb 2024 ### 10/10 Excellent #### David K. Dec 16, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Best place ever Wonderful place with great hosts ##### David K. Stayed 2 nights in Dec 2023 ### 10/10 Excellent #### susan s. Dec 10, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great location and amazing house The property was perfect. Comfortable and spacious while retaining the historic elegance. Hosts were amazing. Answered questions/requests quickly. We had a fantastic stay and cant wait to return. ##### susan s. Stayed 2 nights in Dec 2023 ### 10/10 Excellent #### Len L. Nov 26, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### The best place! We've stayed at a lot of places, but this was by far our favorite--a delightful historic and completely updated house, with a spectacular kitchen. All within walking distance of Chestertown's charming shopping district. Would definitely recommend! ##### Len L. Stayed 4 nights in Nov 2023 ### 10/10 Excellent #### Sondra W. Nov 5, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### November 2023 Thank you! The family enjoyed their stay and loved the ambiance of your B&B and of Chestertown. 🙏❣️👏 ##### Sondra W. Stayed 2 nights in Nov 2023 ### 10/10 Excellent #### Ann S. Oct 30, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Utterly GORGEOUS home and FANTASTIC hosts I cannot say enough good things about our stay at Robert & Beth's home. The listing photos truly don't do justice to this home. It has beautiful historic details (warm, rich woodwork; built in shelving; a doorbell that you turn like a bike bell...) but doesn't feel stuffy or fragile. There is SO much living space to spread out in that our group of six never felt at all cramped. You can easily accommodate four couples or three couples and a family in this home. (The converted attic has two day beds and is accessed THROUGH one of the bedrooms, so not ideal for a 4th couple.) The outdoor space is also lovely. The house has a small, enclosed backyard with a patio table. A great place for happy hour or a sunny breakfast. You can go through the gate to Robert & Beth's adjoining huge garden. The home is as well appointed as the listing describes. And every night stand has a charging station with 3 plugs & 2 USB-As. Not sure if the listing mentioned that. Beth is about the most responsive host we've ever stayed with. I sent several questions before and during our stay and always had a response in under an hour - usually, within minuts. She also sent several suggestions for restaurants in town. No one was staying before or after us, so Robert & Beth graciously allowed us to arrive early and stay for a few extra hours. I would one MILLION PERCENT recommend staying here if you are going to Chestertown. ##### Ann S. Stayed 2 nights in Oct 2023 ### 10/10 Excellent #### Cookie S. Oct 25, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Fabulous house We absolutely loved this house. It was beautiful and immaculate and had everything you would need for your stay. Beth and Bob, the hosts were wonderful to deal with and we really enjoyed chatting with them. We were there for a wedding and wished we had more time to spend in the house since it was so fabulous. It was a quick walk to town and the perfect location. We would highly recommend this house!! Thank you again to Beth and Bob!! ##### Cookie S. Stayed 2 nights in Oct 2023 ### 10/10 Excellent #### Dmitry K. Oct 3, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Amazing Property In the words of my wife: if we could give this house 10 stars, we would. Every detail is thought out, very well appointed property, great hosts. Highly recommended ##### Dmitry K. Stayed 3 nights in Sep 2023 ### 10/10 Excellent #### Deborah K. Aug 26, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautiful property in middle of Chestertown Home is meticulously maintained, located on a quiet cut de sac. Walking distance to the restaurants and shops on Main St. Wonderful amenities -- coffee bar, bottled water, etc. ##### Deborah K. Stayed 2 nights in Aug 2023 ### 10/10 Excellent #### Amy D., Collegeville, PA, USA Jul 31, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Chestertown Fun We were a group of family and friends in Chestertown for a week. Bob and Beth have a beautiful, comfortable house, and there was plenty of room for the seven of us. The house was very clean. The kitchen is equipped with everything you need to have a nice dinner at home. We liked the wine refrigerator, too. We will definitely stay at this property again. ##### Amy D. Stayed 8 nights in Jul 2023 ### 10/10 Excellent #### Donna L. Jul 5, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great property This home was perfect for our family visit. The gardens were so beautiful. The town was just up the block and friendly with shops and restaurants and a Saturday farmers market. The beds were comfortable. The space was homie and convenient. The 6 year old looks up at me on our last night and says. Grandma can’t we just stay here longer. I think we found a winner. ##### Donna L. Stayed 6 nights in Jun 2023 ### 10/10 Excellent #### Peter T. Jun 17, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### A beautiful home. Enjoyed it very much. Trouble with air conditioning first day. After that everything was great. Very beautiful home, ##### Peter T. Stayed 4 nights in Jun 2023 ### 10/10 Excellent #### Mary Beth K. Apr 21, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Spectacular property This house was so beautifully restored with a beautiful family room, dining area for family dinners and comfortable beds. The gardens are spectacular! It feels like a retreat but only a block from High and Cross Streets. We loved it. ##### Mary Beth K. 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