Title: Walk to Historic Chestertown: Dog-friendly Retreat - Latest Reviews, Deals & Photos 2026 - 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 # Walk to Historic Chestertown: Dog-friendly Retreat Cottage in Chestertown with kitchen and fireplace ## 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/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) ![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) - Overview - Location - Amenities - Policies Walk to Historic Chestertown: Dog-friendly Retreat provides everything you need. Stay connected with free WiFi in public areas. ### Entire home 2 bedrooms2 bathroomsSleeps 6957 sq ft ## Popular amenities - Kitchen - Pet friendly - Parking included - Free WiFi - Air conditioning - 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. ### Walk to Historic Chestertown: Dog-friendly Retreat Cottage in Chestertown with kitchen and fireplace Barbecue grills, free self parking, and free WiFi in public areas are available at this smoke-free cottage. The cottage boasts a fireplace and offers a kitchen and 2 bathrooms. Added amenities include a microwave, a stovetop, and a dishwasher. Air-conditioned accommodations at this cottage offer fireplaces. Accommodations at this 3-star cottage have kitchens with stovetops, microwaves, cookware/dishes/utensils, and dishwashers. Bathrooms include showers. ## Property amenities ### Parking and transportation - Free self parking on site ### Kitchen - Blender - Cookware, dishware, and utensils - Dishwasher - Ice maker - Microwave - Oven - Paper towels - Spices - Stovetop ### Bedrooms - 2 bedrooms - Bedsheets provided ### Bathroom - 2 private bathrooms - Shower ### Living spaces - Fireplace - Living room ### Entertainment - Books ### Outdoor areas - Barbecue grill ### Laundry - Laundry detergent ### Comfort - Air conditioning - Heating ### Pets - Pet friendly - Fee: USD 67.89 per accommodation per stay - Service animals exempt from fees ### Suitability/Accessibility - Smoking not allowed ### 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 ![Smart TV](https://images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1199x1y1-75aef492.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cass-N-Reel Luxury Houseboat Grasonville - Kitchen - Free WiFi - Air conditioning - Outdoor Space 10 Exceptional 48 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=94672644&PinnedHotelID=94672644&HadPinnedHotel=true®ionId=-1&adults=2) ![Porch](https://images.trvl-media.com/lodging/118000000/117520000/117514500/117514499/c407e8fd.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Inn at Haven Harbour Rock Hall - Pool - Breakfast included - Pet friendly - Parking included 8.6 Excellent 4 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-02&endDate=2026-02-03&selected=117514499&PinnedHotelID=117514499&HadPinnedHotel=true®ionId=-1&adults=2) ![Library](https://images.trvl-media.com/lodging/76000000/75800000/75794200/75794138/9a26f443.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Hotel Ulysses, a Member of Design Hotels Mount Vernon - Pet friendly - Free WiFi - Restaurant - Air conditioning 9.2 Wonderful 1,000 reviews CA $159 CA $186 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-26&endDate=2026-01-27&selected=75794138&PinnedHotelID=75794138&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 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 ### Property payment types ## 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 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 there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property ## 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 Hazel Miner Monument are also worth visiting. [Visit our Chestertown travel guide](https://www.expedia.ca/Chestertown.dx7215) [View more Cottages in Chestertown](https://www.expedia.ca/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 - Washington College \- 3 min walk \- 0.3 km - River Arts Chestertown \- 11 min walk \- 1.0 km - Wilmer Park \- 14 min walk \- 1.2 km - Historical Society of Kent County Maryland \- 14 min walk \- 1.2 km - Chestertown Historic District \- 14 min walk \- 1.2 km ### Getting around - Baltimore, MD (MTN-Martin State) - 106 min drive ### Restaurants - ‪Royal Farms - ‬12 min walk - ‪Dunkin - ‬2 min drive - ‪McDonald's - ‬3 min drive - ‪Procolino's - ‬2 min drive - ‪7-Eleven - ‬13 min walk ## Frequently asked questions ### Is Walk to Historic Chestertown: Dog-friendly Retreat pet-friendly? ### How much is parking? ### 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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