Entire home

Pet-Friendly Home on Chester River w/ Dock!

Photo gallery for Pet-Friendly Home on Chester River w/ Dock!

A lakeside cabin with a dock extending into the water, surrounded by greenery and boats.
A large house with a well-maintained lawn and a tree with red leaves.
A spacious room with a long window wall, a ceiling fan, and a seating area with a sofa and ottoman.
A dining area with a large wooden table and chairs, a chandelier, and a brick fireplace.
A living room with a sofa, a coffee table, a chandelier, a wooden staircase, and a dining area in the background.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.

Popular amenities

  • Patio
  • Private pool
  • Barbecue grill
  • Air conditioning
  • Pet-friendly
  • Onsite parking available

Explore the area

View in a map
Chestertown, MD
  • Place, Kings Town Park
    ‪9 min walk‬
  • Place, Chestertown Historic District
    ‪3 min drive‬
  • Place, River Arts Chestertown
    ‪3 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪129 min drive‬

Rooms & beds

4 bedrooms (sleeps 14)

Additional Sleeping (Game Room)

2 Double Sofa Beds

Additional Sleeping (Sunroom)

1 Double Sofa Bed

Bedroom 1

1 Queen Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Queen Beds

Bedroom 4

2 Twin Beds

4 bathrooms, 1 half bathroom

Full Bathroom

Full Bathroom

Full Bathroom

Full Bathroom

Half Bathroom

Spaces

Deck or patio
Kitchen
Separate dining area
Garden

Add dates for prices

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  • Kitchen
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About the neighborhood

Chestertown

Chestertown is home to this vacation 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 an opportunity to explore the area for water adventures such as kayaking.
View more Vacation Homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Kings Town Park - 9 min walk - 0.8 km
  • 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
  • Sumner Hall - 3 min drive - 2.8 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 106 min drive

Restaurants

  • ‪Royal Farms - ‬3 min drive
  • ‪McDonald's - ‬5 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 Nov 4, 2026, prices found for a 1-night stay for 2 adults at Pet-Friendly Home on Chester River w/ Dock! on Nov 5, 2026 start from $890, 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 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!?

Check-out is at 10:00 AM.

Where is Pet-Friendly Home on Chester River w/ Dock! located?

Situated in Chestertown, this vacation home is within 1 mi (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 mi (3 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 21 out of 28 reviews
Rating 8 - Good. 6 out of 28 reviews
Rating 6 - Okay. 1 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 0 out of 28 reviews

9.8/10

Cleanliness

9.6/10

Check-in

9.2/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great view and super cute town
Stayed 4 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house! We will book again.
Stayed 2 nights in Sep 2026
From a partner site

10/10 Excellent

Jessica

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!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Sunset over the Chester River.
Stayed 2 nights in Apr 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Location!!! Pool was nice a dock was excellent
Stayed 5 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, location, listing accuracy
Nice property great location pause great very pet pet friendly and George fishing off the dock
Stayed 6 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a minor issue at check in that was resolved quickly, efficiently and beyond expectations. We will be back!
Stayed 5 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful get away for group of friends. We loved cooking thanks to well stocked kitchen, enjoyed the pool, and played games. Hoping to visit again.
Stayed 4 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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

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!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Goetsch family vacation 2025

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

Perfect home for family gathering in Chestertown

Perfect home for family gathering in Chestertown.Clean, great space, great kitchen supplies.Just as listed 🤗
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing views!

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

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.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice property

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

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.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

205 Fey Rd

Property was in great shape. Great view of the water and all had a great time!
Stayed 2 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful location

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.
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Winter Hunting Trip Rental

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!!!
Stayed 3 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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

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 Jul 14, 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.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 4 nights in Jun 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

5 generation vacation

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.
Stayed 7 nights in Jun 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

not enough equipment

no kettle no cutting board
Stayed 2 nights in Nov 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Jul 2026
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