• Embrace historic charm in our exquisitely renovated third-floor walk-up, located in a beautiful historic building in the Chestertown Historic District.
• Perfectly positioned to overlook Fountain Park and within walking distance of Washington College and all of downtown Chestertown.
• Enjoy unique furnishings that blend early 1900s decor with modern comforts.
• Indulge in luxury amenities with priority booking access at Park Row Floats, a renowned exclusive Float Spa located just below the space.
Pippin’s Retreat offers:
• Two bedrooms, each featuring a queen bed.
• Two full bathrooms, with the primary bedroom offering an ensuite.
• A large, fully-equipped modern kitchen with a view of Fountain Park.
• A comfortable living room with characteristic furnishings, opening onto a sizeable back deck - perfect for relaxing or entertaining.
• We use Melaleuca's nontoxic, plant-based cleaning products to ensure a healthy, chemical-free environment for your stay.
Guest access • You will have the entire third floor to yourself, including the large back deck that provides an elevated view across the historic rooftops of Chestertown.
• Access through the rear exterior staircase or enjoy walking up the original historic stairway inside the main front lobby, with its charmingly narrow design reflective of the early era.
Other things to note • We cherish the building's historic elements and ask guests to be mindful of the unique charm of the narrow staircase.
• Visit the Park Row Floats website to make a Spa appointment.
• We use Melaleuca's nontoxic, plant-based cleaning products to ensure a healthy, chemical-free environment for your stay. These eco-friendly cleaners leave your space fresh and welcoming, perfect for guests with sensitivities or anyone looking to avoid harsh chemicals. Relax knowing your comfort and the planet are prioritized - ideal for Washington College parents cheering on their students!
Our prices include all fees. No hidden fees.
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Important information
You need to know
Property # 4670523
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
Onsite parties or group events are strictly prohibited
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
About the neighborhood
Chestertown
Located in Chestertown, this apartment is in the city center. 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. Larrabee Arts Center and Crumpton Auction are also worth visiting.
How much does it cost to stay at Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access?
As of May 12, 2026, prices found for a 1-night stay for 2 adults at Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access on May 13, 2026 start from $364, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking?
Onsite parking is available at the property.
What time is check-in at Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access?
Check-in begins at 3:00 PM.
What time is check-out at Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access?
Check-out is at 11:00 AM.
Where is Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access located?
Located in the heart of Chestertown, this apartment building is steps from River Arts Chestertown, Historical Society of Kent County Maryland, and Garfield Center for the Arts at the Prince Theater. Chestertown Historic District and Sumner Hall are also within 10 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Liked: Cleanliness, amenities, property conditions & facilities, communication
We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it.