Accommodating 14 guests, this vacation home features 4 bedrooms and 4 bathrooms. It offers kayaking as an adventure activity nearby. Guests can enjoy a patio for outdoor relaxation. The property is pet-friendly and is also close to Kings Town Park and the Historical Society of Kent County Maryland.
Highlights
Dive into relaxation
Unwind in the top-rated pool, your perfect spot for relaxation.
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 -Â Flat-screen TV -Â Office w/ L-shaped desk, printer & monitor - Furnished sunroom w/ pool view -Â 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 Schooner Sultana. Larrabee Arts Center and Crumpton Auction 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
Historical Society of Kent County Maryland - 3 min drive - 2.4 km
River Arts Chestertown - 3 min drive - 2.8 km
Wilmer Park - 3 min drive - 2.8 km
Getting around
Baltimore, MD (MTN-Martin State) - 106 min drive
Restaurants
‪McDonald's - ‬5 min drive
‪Royal Farms - ‬3 min drive
‪Dunkin - ‬4 min drive
‪Procolino's - ‬4 min drive
‪Royal Farms - ‬2 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 6 Oct 2026, prices found for a 1-night stay for 2 adults at Pet-Friendly Home on Chester River w/ Dock! on 22 Oct 2026 start from AU$2,882, 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).
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Our whole family had a fantastic visit to this property! Wonderful pool, morning coffee on the dock, sunset views in the evening and close, easy access to the main street with shops and restaurants. The hosts were extremely responsive when there were some minor weather related issues. The property was clean and well stocked. Would definitely stay again!
Stay was very nice. Enjoyed ourselves. Kitchen was well-stocked. Lots of space to spread out. Wished the weather was nicer to enjoy fishing off the dock.
This was a fantastic place, the best. Pool was such a plus. Fishing, crabbing, drinks poolside and beautiful scenery. Great place for family gathering.
Stayed 7 nights in Jul 2025
From a partner site
10/10 Excellent
Kevin
30 June 2025
Coffee on the dock.
We had a great family vacation in Chestertown. We enjoyed the pool and beautiful views of the water. It was a great place to be durning the heat wave!
What a perfect house for a family vacation. My grandkids said this was the best vacation yet ! They loved fishing , crabbing and kayaks. The pool was another great feature. Definitely want to stay here again.
Stayed 4 nights in Jul 2025
From a partner site
10/10 Excellent
Patricia
16 Oct 2025
Perfect home for family gathering in Chestertown
Perfect home for family gathering in Chestertown.Clean, great space, great kitchen supplies.Just as listed 🤗
A large sprawling house that’s perfect for groups, this property offers stunning views of the Chester River. We spent every evening of our stay sitting along the water.
Stayed 3 nights in May 2025
Verified review
8/10 Good
WILLIAM P.
1 June 2026
Liked: Cleanliness, location, listing accuracy
The house was large enough to accommodate our group and we enjoyed the dock and porch. We were surprised to find the outside had a parked trailer and cars that looked like they had been there for a long time. Although the weather prohibited us from using the pool is was not clean and ready to use.
Pictures accurately describe the house. One of the full baths is off the kitchen which was a little strange, but overall recommend. Lots of shoreline and great views.
Stayed 3 nights in Apr 2025
From a partner site
10/10 Excellent
Tori
7 Nov 2024
Excellent stay
This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around.
This is a nice house beautifully situated on the Chester River. We were there only for two nights for a graduation but everyone wished it was longer so we could have enjoyed more. House is just as described. Plenty of room and well stocked.
An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!
Perfect for our reunion, coming together from four home locations. Kitchen was very well stocked . Everything needed to enjoy steamed crabs was available. Clean linens and towels. Helpful feedback, when needed.
Stayed 2 nights in Oct 2025
Verified review
6/10 Okay
Karen B.
5 July 2026
Liked: Check-in
The air conditioning was not working for parts of the day where it shut off. Kitchen area base of refrigerator and under stove were not clean. No pool towels provided.
Stayed 7 nights in Jun 2026
Response from VrboOwner on 14 July 2026
Thank you for sharing your feedback. We apologize that your stay did not meet expectations. As soon as we were notified of the A/C concern, we contacted our HVAC technician, who inspected the system and did not identify any mechanical issues. During periods of unusually high temperatures, temporary power fluctuations can occasionally affect cooling performance. Our home is professionally cleaned before each guest's arrival, and we've shared your comments about the kitchen with our cleaning team for review. We also wish you had reached out about the pool towels during your stay, as we would have been happy to provide additional towels right away to make your stay more comfortable.
The house was almost perfect. Would like to give it a 4 3/4 Star! When they replace the dishwasher, and add a railing on the pool steps, it will be perfect! We are hoping to come back next June!
My family and I had a wonderful time at this home. This was are first year for 5 generations getting together from 4 months old to 85 years old. From swimming in the pool to swimming in the river, kayaking, another family activities. Great time had by all. Place was clean and stocked with everything we needed for are stay. Only could one crab 8 1/4 long still to early in the season.
Very nice place — had trouble with televisions and computer never turned on. Not too big a deal for our family as we were more than happy to unplug and spend majority of time outside. We did have a couple of senior members that were a little disappointed without use of the tv and computer though. All in all an excellent location and pleasant experience.