Title: Walk to Historic Chestertown: Dog-Friendly Retreat 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 # Walk to Historic Chestertown: Dog-Friendly Retreat Holiday home in Chestertown with kitchen and patio ## Photo gallery for Walk to Historic Chestertown: Dog-Friendly Retreat ![Exterior - Walk to Historic Chestertown: Dog-Friendly Retreat (Chestertown)](https://images.trvl-media.com/lodging/123000000/122290000/122287000/122286944/bdf0b7fe.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Fridge, microwave, stovetop, dishwasher - Walk to Historic Chestertown: Dog-Friendly Retreat (Chestertown)](https://images.trvl-media.com/lodging/123000000/122290000/122287000/122286944/05b87fee.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Walk to Historic Chestertown: Dog-Friendly Retreat (Chestertown)](https://images.trvl-media.com/lodging/123000000/122290000/122287000/122286944/997e5b29.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining - Walk to Historic Chestertown: Dog-Friendly Retreat (Chestertown)](https://images.trvl-media.com/lodging/123000000/122290000/122287000/122286944/1df1cf6a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![TV, fireplace, books - Walk to Historic Chestertown: Dog-Friendly Retreat (Chestertown)](https://images.trvl-media.com/lodging/123000000/122290000/122287000/122286944/5c41fb17.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Walk to Historic Chestertown: Dog-Friendly Retreat provides a garden and more. ## Reviews 10 Exceptional ### Entire home 2 bedrooms2 bathrooms967 sq ft ## Popular amenities - Kitchen - Washing machine - Dryer - Pet-friendly - 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. ### Walk to Historic Chestertown: Dog-Friendly Retreat Fenced Backyard | Furnished Deck | Family Game Nights Step into a storybook at 'Sage Bungalow' in Chestertown, where historic streets and riverside breezes set the scene for adventure. Head downtown to explore local art galleries, enjoy a picnic in the leafy serenity of Wilmer Park, or glide along the Chester River on a boat cruise. After a fun day, retreat to the 2-bed, 2-bath home to cozy up by the fire or settle in for a night of board games. Your Eastern Shore escape awaits! \-- THE PROPERTY -- SLEEPING ARRANGEMENTS \- Bedroom 1: 1 king bed \- Bedroom 2: 1 queen bed \- Living Room: 1 queen sleeper sofa OUTDOOR LIVING \- Deck w/ dining space & charcoal grill \- Covered porch w/ 2 chairs \- Fenced backyard INDOOR LIVING \- Smart TV, fireplace \- Dining table \- Walk-in shower, shower/tub combo \- Board games, books KITCHEN \- Stove/oven, refrigerator, dishwasher \- Cooking basics, dishware/flatware \- Cuisinart dual coffee maker (drip & single-serve pod, coffee provided) \- Microwave, toaster, blender, ice maker \- Limited spices (salt, pepper, garlic salt, paprika, tajin, cinnamon & dill weed) GENERAL \- Free WiFi \- Central heating & A/C \- Complimentary toiletries, hair dryer \- Washer/dryer, laundry detergent, hangers \- Linens/towels, trash bags/paper towels FAQ \- Pet fee (paid pre-trip) ACCESSIBILITY \- Single-story home, 8 steps to enter PARKING \- Driveway (1 vehicle) \- EV outlet (bring your own charging cable) \-- THE LOCATION -- \- 0.3 miles to Washington College \- 0.5 miles to Historical Society of Kent County \- 0.7 miles to Chestertown Historic District: Chestertown Farmers Market (every Saturday from 8:00 AM to 12:00 PM), Chestertown Tea Party Festival (Memorial Day weekend), parks, restaurants, art galleries, shops \- 1 mile to Chester River \- 18 miles to Eastern Neck National Wildlife Refuge \- 67 miles to Baltimore/Washington International Airport \-- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7\. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. \-- POLICIES -- \- No smoking \- Pet friendly w/ $50 fee (+ fees & taxes, dogs only, 2 max) \- No events, parties, or large gatherings \- Must be at least 18 years old to book \- Additional fees and taxes may apply \- Photo ID may be required upon check-in ADDITIONAL INFORMATION \- This single-story home requires 8 steps to enter ## Property amenities ### Internet - Available in the house: Internet access ### Parking and transport - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Hob - Ice maker - Microwave - Refrigerator - Spices - Toaster ### Dining - Dining table ### Bedrooms - 2 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Hair dryer - Towels provided ### Living spaces - Dining table - Fireplace ### Entertainment - Books - Games - TV ### Outdoor areas - Barbecue grill - Garden - Patio ### Laundry - Washing machine ### Comfort - Air conditioning - Heating ### Pets - Pet friendly ### Suitability/Accessibility - Smoke-free property ### 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 ### General - Garden - Unit size: 967 square feet ## 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 875 reviews £82 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-01&endDate=2026-03-02&selected=1700736&PinnedHotelID=1700736&HadPinnedHotel=true®ionId=-1&adults=2) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/799945fa.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Red Roof Inn & Suites Chestertown Chestertown - Pet-friendly - Parking included - Free Wi-Fi - Air-conditioning 7.2 Good 427 reviews £59 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24&selected=40352&PinnedHotelID=40352&HadPinnedHotel=true®ionId=-1&adults=2) ![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 1 Mar - 2 Mar [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-01&endDate=2026-03-02&selected=96826266&PinnedHotelID=96826266&HadPinnedHotel=true®ionId=-1&adults=2) ![House (2 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/123000000/122310000/122304600/122304590/4dabad4d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Walk to Historic Chestertown: Dog-friendly Retreat Chestertown - Kitchen - Pet-friendly - Parking included - Free Wi-Fi [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-02&endDate=2026-03-03&selected=122304590&PinnedHotelID=122304590&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/w1322h734x2y1-d973a563.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### First Floor Studio Apartment in Historic Chestertown Chestertown - Pool - Washing machine - Dryer - Free Wi-Fi 9.6 Exceptional 108 reviews £119 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-02-17&endDate=2026-02-18&selected=75854900&PinnedHotelID=75854900&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-03-02&endDate=2026-03-03&selected=122286944&PinnedHotelID=122286944&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=122286944,1700736,40352,96826266,122304590) ## Policies ### Check-in Check-in time starts at 3:00 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 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 Note from host: A maximum of 2 pets are 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 professional host. The provision of housing is linked to their trade, business or profession. 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 and a first aid kit This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room 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 If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal. ### Property is also known as 552688 ## About the area Chestertown is home to this holiday home. The area's natural beauty can be seen at Chestertown Historic District and Wilmer Park, while Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland are cultural highlights. [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%7C39.21377%2C-76.07378&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=LeMMAcV6SGW0VOtd9i253MKObHE=) Chestertown, Maryland ### 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 3 min walk \- 0.2 miles - River Arts Chestertown 11 min walk \- 0.6 miles - Garfield Center for the Arts at the Prince Theater 13 min walk \- 0.7 miles - Wilmer Park 14 min walk \- 0.8 miles - Historical Society of Kent County Maryland 14 min walk \- 0.8 miles ### Getting around - Baltimore, MD (MTN-Martin State) 106 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 12 min walk ## Frequently asked questions ### Is Walk to Historic Chestertown: Dog-Friendly Retreat pet-friendly? ### How much is parking at Walk to Historic Chestertown: Dog-Friendly Retreat? ### What time is check-in at Walk to Historic Chestertown: Dog-Friendly Retreat? ### What time is check-out at Walk to Historic Chestertown: Dog-Friendly Retreat? ### Where is Walk to Historic Chestertown: Dog-Friendly Retreat located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Walk to Historic Chestertown: Dog-Friendly Retreat 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 1 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 10 Location ## Reviews ### 10/10 Excellent #### Gary F. 26 Dec 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Highly recommend if you're staying in Chestertown. Everything is near by and the comforts and quality of stay are above the five star review. Comfortable and warm home with all the amenities. Just bring some personable items and your set. Fairly priced too! Definitely would stay again.Thank you! ##### Gary F. 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