Calling all outdoor explorers! Lower your anchor at this 4-bedroom, 4.5-bath vacation rental in Chestertown. With an enclosed porch, a boat dock right on the Chester River, and a basement game room, this spacious abode promises endless family fun! When you're ready to explore, head 1 mile to the Historic District for sightseeing, souvenir shopping, local seasonal events, and of course, the Chestertown Farmer's Market.
-- THE PROPERTY --
SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 king bed - Bedroom 3: 2 queen beds - Bedroom 4: 1 twin daybed w/ 1 twin trundle (convertible to 1 king bed) - Sunroom: 1 queen sleeper sofa - Game Room: 2 queen futons - Additional Sleeping: 1 portable crib
INDOOR LIVING - Flat-screen TV - Office w/ L-shaped desk, printer & monitor - Furnished sunroom w/ pool view - Dining tables
OUTDOOR LIVING - Large yard w/ tree swing - Enclosed 20' x 40' porch w/ dining areas - Charcoal grill (charcoal provided), gas grill (propane provided) - Seasonal outdoor pool (May 15-September 15)
GENERAL - Free WiFi - Central A/C, heat pump w/ electric backup, ceiling fans - Iron & board, hangers - Linens & towels, hair dryer
FAQ - Pet fee (paid pre-trip, 3 pets max)
ACCESSIBILITY - Multi-level home, 6 steps to enter - Bedroom & bathroom on 1st floor
PARKING - Driveway (8 vehicles)
-- THE LOCATION --
- Walking distance to a sandy beach along the Chester River - Under 1 mile to Chestertown's shops, restaurants, schooners & sailing ships - 2 miles to Washington College - 1 mile to Historical Society of Kent County - 67 miles to Baltimore/Washington International Thurgood Marshall 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/ $100 fee (+ fees & taxes, 3 pets max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in
ADDITIONAL INFORMATION - This multi-level home requires 6 steps to enter - The seasonal outdoor pool is open from May 15 to September 15 -Pets are not allowed on the 2nd floor rooms. Please keep pets on the 1st floor or basement and do not let them in 2nd floor rooms.
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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
About the area
Chestertown
Chestertown is home to this holiday home. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center. Crumpton Auction and The Mainstay are also worth visiting. Take the opportunity to explore the area for water adventures such as kayaking.
Chestertown Historic District - 3 min drive - 2.4 km
Garfield Center for the Arts at the Prince Theater - 3 min drive - 2.4 km
Historical Society of Kent County Maryland - 3 min drive - 2.4 km
Washington College - 3 min drive - 3.1 km
Getting around
Baltimore, MD (MTN-Martin State) - 106 min drive
Restaurants
Milano's Pizzeria - 3 min drive
McDonald's - 5 min drive
Dunkin - 4 min drive
Royal Farms - 3 min drive
Cafe Sado - 4 min drive
Frequently asked questions
Is Pet-Friendly Home on Chester River w/ Dock! pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Pet-Friendly Home on Chester River w/ Dock!?
As of 21 Aug 2026, prices found for a 1-night stay for 2 adults at Pet-Friendly Home on Chester River w/ Dock! on 9 Sept 2026 start from AU$2,782, 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 at Pet-Friendly Home on Chester River w/ Dock!?
On-site parking is available at the property.
What time is check-in at Pet-Friendly Home on Chester River w/ Dock!?
Check-in begins at 4:00 PM.
What time is check-out at Pet-Friendly Home on Chester River w/ Dock!?
Checkout is at 10:00 AM.
Where is Pet-Friendly Home on Chester River w/ Dock! located?
Situated in Chestertown, this holiday home is within 1 mile (2 km) of Kings Town Park and Historical Society of Kent County Maryland. Chestertown Historic District and Garfield Center for the Arts at the Prince Theater are also within 2 miles (3 km).