Title: Country Estate in Historic District Reviews, Deals & Photos 2026 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Country Estate in Historic District Family-friendly holiday home in Chestertown ## Photo gallery for Country Estate in Historic District ![Property grounds - Country Estate in Historic District (Chestertown)](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/adbcc20f.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Interior - Country Estate in Historic District (Chestertown)](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/1723fbc6.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Country Estate in Historic District (Chestertown)](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/8ea498ee.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Terrace/patio - Country Estate in Historic District (Chestertown)](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/ac926317.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Country Estate in Historic District (Chestertown)](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/23141e99.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies 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. ## Reviews 10 Exceptional ### Entire home 5 bedrooms4 bathroomsSleeps 10 ## Popular amenities - Kitchen - Washing machine - Dryer - Pet-friendly - Air-conditioning ## 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 transport - Parking on site ### Kitchen - Blender - Coffee grinder - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Electric kettle - Hob - Ice maker - Kitchen island - Microwave - Oven - Paper towels - Refrigerator - Spices - 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 - Smoke-free property - Note from host: No smoking on property. ### Services and conveniences - Iron/ironing board ### Location highlights - In the city centre ### 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 ![Private beach nearby, sun-loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Lodge at Great Oak Landing Chestertown - Pool - Parking included - Free Wi-Fi - Restaurant 7.8 Good 77 reviews £90 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-02&endDate=2026-03-03&selected=96826266&PinnedHotelID=96826266&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-03-03&endDate=2026-03-04&selected=54841025&PinnedHotelID=54841025&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=54841025,96826266) ## Policies ### Check-in Check-in time starts at 4:00 PM Contactless check-in and check-out are 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 Information provided by the property may be translated using automated translation tools ### Pets Pets are allowed Service animals are welcome, and are exempt from fees Restrictions apply; for more information contact the property on 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 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 Note from host: No parties. 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, a first aid kit and a deadlock 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 Located in Chestertown, this holiday home is in the city centre. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Chestertown Historic District and Wilmer Park. [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%7C39.21173%2C-76.06716&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=NfEuNT1VqcC_GG0OchD0ynyizwE=) 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 \- 0.5 miles - River Arts Chestertown 5 min walk \- 0.3 miles - Garfield Center for the Arts at the Prince Theater 6 min walk \- 0.4 miles - Historical Society of Kent County Maryland 8 min walk \- 0.5 miles - Wilmer Park 9 min walk \- 0.5 miles ### Getting around - Baltimore, MD (MTN-Martin State) 105 min drive ### Restaurants - Milano's Pizzeria 4 min drive - Royal Farms 4 min drive - Dunkin 2 min drive - McDonald's 3 min drive - Royal Farms 5 min walk ## Frequently asked questions ### Is Country Estate in Historic District pet-friendly? ### How much is parking at Country Estate in Historic District? ### What time is check-in at Country Estate in Historic District? ### What time is check-out at Country Estate in Historic District? ### Where is Country Estate in Historic District located? ## 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 ## 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 73 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 10 Location ## Reviews ### 10/10 Excellent #### Elder p. 4 May 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. 2 Mar 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 #### Len L. 26 Nov 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 #### Deborah K. 26 Aug 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 #### susan s. 10 Dec 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 #### Sondra W. 5 Nov 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 #### Diana M. 20 Oct 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 #### Cookie S. 25 Oct 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 #### Ann S. 30 Oct 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 #### Robin G. 15 Jun 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 #### Judie G. 8 Sept 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Such a lovely restored spacious comfortable home. We keep coming back! Friendly gracious hosts. Highly recommended’ ##### Judie G. Stayed 3 nights in Sep 2025 ### 10/10 Excellent #### Chris W. 15 Oct 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stay! Great stay! ##### Chris W. Stayed 2 nights in Oct 2023 ### 10/10 Excellent #### Gwen R. 11 Jun 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 #### David K. 16 Dec 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 #### ira d. 6 Jul 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 #### Susan N. 30 Jan 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### walking distance to downtown and historic Chestertown and campus. well located. A lovely home and amenities. We had a winderful stay. ##### Susan N. Stayed 2 nights in Jan 2023 ### 10/10 Excellent #### Stephen C. 11 Nov 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 #### Margaret H., Ocean View, DE 31 Oct 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stay in Chestertown Loved this property. So beautiful and well equipped. Beds were very comfy. Walking distance to everything in town. ##### Margaret H. Stayed 3 nights in Oct 2022 ### 10/10 Excellent #### sue B. 12 Apr 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Welcome We felt at home, comfortable and welcomed. Great to be in walking distance to charming Chestertown, a safe and lovely town with a super Saturday market. ##### sue B. Stayed 7 nights in Apr 2023 ### 10/10 Excellent #### Dmitry K. 3 Oct 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 #### Tom L., Wilmington, DE 16 Aug 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great family vacation in Chestertown! We had a wonderful time. Our hosts were great and communication was timely and very accommodating. The home and grounds were a great setting for our vacation. We were most grateful for the special touches that made us feel quite welcome. Thank you! ##### Tom L. Stayed 5 nights in Aug 2021 ### 10/10 Excellent #### Karen J. 25 Aug 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### perfect wedding weekend! Wonderfully renovated historic property in the middle of town. Lots of room and super clean...Fresh flowers greeted us upon arrival. Just wonderful. ##### Karen J. Stayed 4 nights in Aug 2021 ### 10/10 Excellent #### Mary Beth K. 21 Apr 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. Stayed 5 nights in Apr 2023 ### 10/10 Excellent #### Mary S., Alexandria, Virginia 1 Apr 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. 27 Aug 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. 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