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=&selected=122304590&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Walk to Historic Chestertown: Dog-friendly Retreat ## Photo gallery for Walk to Historic Chestertown: Dog-friendly Retreat ![House (2 Bedrooms) | Front of property - Walk to Historic Chestertown: Dog-friendly Retreat (Chestertown)](https://images.trvl-media.com/lodging/123000000/122310000/122304600/122304590/4dabad4d.jpg?impolicy=resizecrop&rw=598&ra=fit) ![House (2 Bedrooms) | Interior - Walk to Historic Chestertown: Dog-friendly Retreat (Chestertown)](https://images.trvl-media.com/lodging/123000000/122310000/122304600/122304590/f7a23006.jpg?impolicy=resizecrop&rw=297&ra=fit) ![House (2 Bedrooms) | Interior - Walk to Historic Chestertown: Dog-friendly Retreat (Chestertown)](https://images.trvl-media.com/lodging/123000000/122310000/122304600/122304590/1fa0e16e.jpg?impolicy=resizecrop&rw=297&ra=fit) ![House (2 Bedrooms) | Interior - Walk to Historic Chestertown: Dog-friendly Retreat (Chestertown)](https://images.trvl-media.com/lodging/123000000/122310000/122304600/122304590/c1dec1ae.jpg?impolicy=resizecrop&rw=297&ra=fit) ![House (2 Bedrooms) | Interior - Walk to Historic Chestertown: Dog-friendly Retreat (Chestertown)](https://images.trvl-media.com/lodging/123000000/122310000/122304600/122304590/cdfc628c.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Walk to Historic Chestertown: Dog-friendly Retreat provides everything that you need. Stay connected with free WiFi in public areas. ### Entire home 2 bedrooms2 bathroomsSleeps 6957 sq ft ## Popular amenities - Kitchen - Washing machine - Pet-friendly - Parking included - Free Wi-Fi - Air-conditioning ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire cottage to yourself and will only share it with other guests in your party. ### Walk to Historic Chestertown: Dog-friendly Retreat Barbecues, free self-parking and free Wi-Fi in public areas are available at this smoke-free cottage. The cottage boasts a fireplace and offers a kitchen and a washing machine. Guests can appreciate conveniences, such as 2 bathrooms and a microwave, and other amenities include a stovetop and a dishwasher. Air-conditioned accommodation at this cottage offers fireplaces. Accommodation at this 3-star cottage has kitchens with stovetops, microwaves, kitchenware and utensils and dishwashers. Bathrooms include a shower. ## Property amenities ### Parking and transport - Free self parking on site - Limited on-site self parking ### Kitchen - Blender - Cookware, dishware, and utensils - Dishwasher - Hob - Ice maker - Microwave - Oven - Paper towels - Spices ### Bedrooms - 2 bedrooms - Bedsheets provided ### Bathroom - 2 private bathrooms - Shower ### Living spaces - Fireplace - Living room ### Entertainment - Books - Games ### Outdoor areas - Barbecue grill ### Laundry - Laundry detergent - Washing machine ### Comfort - Air conditioning - Heating ### Pets - Pet friendly - Fee: USD 67.89 per accommodation per stay - Service animals exempt from fees ### 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) ## 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 880 reviews £84 includes taxes & fees 15 Mar - 16 Mar [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-15&endDate=2026-03-16&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 429 reviews £60 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-04-05&endDate=2026-04-06&selected=40352&PinnedHotelID=40352&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor banquet area](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/w2877h1800x0y0-f772721c.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Tilghman Island Inn Tilghman - Pool - Breakfast included - Pet-friendly - Parking included 9.6 Exceptional 124 reviews £132 includes taxes & fees 6 Mar - 7 Mar [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-06&endDate=2026-03-07&selected=59854328&PinnedHotelID=59854328&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/79000000/78090000/78088600/78088587/b47c715d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Solomons Victorian Inn Solomons - Breakfast included - Parking included - Free Wi-Fi - Air-conditioning 10 Exceptional 35 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-19&endDate=2026-03-20&selected=78088587&PinnedHotelID=78088587&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 £122 includes taxes & fees 9 Mar - 10 Mar [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-09&endDate=2026-03-10&selected=75854900&PinnedHotelID=75854900&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-03-19&endDate=2026-03-20&selected=122304590&PinnedHotelID=122304590&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=122304590,1700736,40352,59854328,78088587) ## Policies ### Check-in Check-in start time: 3:00 PM; check-in end time: 12:00 AM ### Check-out Check-out before 11:00 AM ### Special check-in instructions The check-in location differs from the property location; go to: \[apartment\] Guests must contact the property for check-in information To make arrangements for check-in please contact the property at least 48 hours before arrival using the information on the booking confirmation Information provided by the property may be translated using automated translation tools ### Pets Pets are allowed for an extra charge of USD 67.89 per accommodation, per stay Service animals are welcome, and are exempt from fees ### Children and extra beds Children are welcome ### Smoking Smoking is not permitted ### Payment types at the property ## Important information ### Optional extras - Pet fee: USD 67.89 per accommodation, per stay - Service animals are exempt from fees The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change. ### 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 This property accepts credit cards; cash is not accepted 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 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. ## About the area Chestertown is home to this cottage. Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland are cultural highlights, and some of the area's activities can be experienced at Rolphs Wharf Marina and Cassinelli Winery and Vineyards. Crumpton Auction and The Mainstay are also worth visiting. [Visit our Chestertown travel guide](https://www.expedia.co.uk/Chestertown.dx7215) [View more Cottages in Chestertown](https://www.expedia.co.uk/Chestertown-Cottages.d7215-aaCottages.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=39.21134,-76.075455&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:_jjnFpnioM%3FQ%3FU%40S%3FS%40S%40S%40U%40Q%40S%40SBS%40SBSBSBSBSBQBSDSDQBSDQDQDQDQFSDQFQFQDOHSFOFOFQHOFQHOFOHOHOJMHOHOHKJOHMJMJMJMJKJKJMJKLKJKJILKLKJILILILILILGLGLILGNELGLGLENENELENELENCLCNCNCNCLANCN%3FNCNAL%3FN%3FN%3FN%3FN%3FN%3FN%3FL%3FN%40NBN%3FLBN%40NBNBLBNBNBLDNDLDNDLDNDLFLFLDNFLHLFLFLHLHLHJHLHLJJJLHJJJJLJJLJJJJJLJLHLJLHNJJHNHNHLHNHNHNFNHPHNFPFNFNFRFNFPDPFPDRFPDPDPBRDPDPBRDRBPBRBRBRBR%40R%40RBR%40R%40P%40T%40R%3FR%40R%3FR%3FT%3FP%3FR%3FT%3FRAR%3FRARARARARCRARARCRCRCRCRCPERCREPEPCREPEPGPEPGREPGPGNGPGPGNGPININGPILIPILININILKLINKLILKJKLKJKLKJMLKJKJMHKJMJMHKHMHMFMJMFMFMHODMFMFMFODMDODMDODMBODOBMBOBO%40OBM%40O%40OBO%3FM%3FO%40O%3FO%3FO%3FO%3FOAM%3FO%3FOCOAOAMCOAOCOCMCOEMCOEMEOEOEMEMGMGOGMEMIMGMGMKMGMIMIKIMKMKKIKKMKKMKKKKKMKMKKKMIMKOIMIMIOKOIMIQGMIQGOIOGQGOGQIQEOGQGQESGQEQEQEQEQCSEQESCSCQCSCSCSCSASCSASASASASASAS%3FSAS%3FU%3FS&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=Q1qFQ0eFRw7j3SC8BqhIYQXT8S0=) 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 3 min walk \- 0.2 miles - River Arts Chestertown 11 min walk \- 0.6 miles - Wilmer Park 14 min walk \- 0.8 miles - Historical Society of Kent County Maryland 14 min walk \- 0.8 miles - Chestertown Historic District 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? 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