Entire home

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

Photo gallery for The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

A porch with white rocking chairs, a small round table, and a window with shutters.
A living room with a fireplace, a sofa, and a coffee table.
A living room with a beige sofa, a wooden coffee table, and a black leather chair. There are windows with white shutters, a painting on the wall, and a lamp on a side table.
A wooden staircase with a white door at the top and a window on the right.
A residential street with houses, parked cars, and American flags.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Onsite parking available
    Convenient and secure onsite parking, a rare amenity in the area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Washington College

Popular amenities

  • Patio
  • Toys
  • Barbecue grill
  • Air conditioning
  • Off-street parking available
  • Refrigerator

Explore the area

View in a map
Chestertown, MD
  • Place, Chestertown Historic District
    ‪2 min walk‬
  • Place, River Arts Chestertown
    ‪5 min walk‬
  • Place, Washington College
    ‪9 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪126 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Double Bed

Bedroom 3

2 Twin Beds

3 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo

Bathroom 3

Soap · Towels provided · Toilet · Shower only · Shampoo

Spaces

Deck or patio
Porch or lanai
Kitchen

Add dates for prices

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  • Hot tub
  • Kitchen
  • Washer
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10.0 out of 10, Exceptional, (118 reviews)
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About the neighborhood

Chestertown

Chestertown is home to this vacation home. Historical Society of Kent County Maryland and Betterton Historic District are local landmarks, and some of the area's activities can be experienced at Rolphs Wharf Marina and Cassinelli Winery and Vineyards. Garfield Center for the Arts at the Prince Theater and Schooner Sultana are also worth visiting.
View more Vacation Homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Historical Society of Kent County Maryland - 1 min walk - 0.0 km
  • Chestertown Historic District - 2 min walk - 0.2 km
  • River Arts Chestertown - 5 min walk - 0.4 km
  • Sumner Hall - 5 min walk - 0.4 km
  • Washington College - 9 min walk - 0.8 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 107 min drive

Restaurants

  • ‪Royal Farms - ‬4 min drive
  • ‪McDonald's - ‬4 min drive
  • ‪Dunkin - ‬2 min drive
  • ‪Procolino's - ‬3 min drive
  • ‪Royal Farms - ‬3 min walk

Frequently asked questions

Is The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown?

As of Nov 13, 2026, prices found for a 1-night stay for 2 adults at The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown on Nov 23, 2026 start from $489, 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.

Where is The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown located?

Situated in Chestertown, this vacation home is steps from Historical Society of Kent County Maryland, Chestertown Historic District, and Garfield Center for the Arts at the Prince Theater. Sumner Hall and Chestertown Farmers Market are also within 5 minutes.

Reviews

9.8

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. 8 out of 9 reviews
Rating 8 - Good. 1 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely and welcoming home. Chestertown is a beautiful town and everything was within walking distance.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfectly located, EZ process, highly responsive owner made this a perfect place for friends to stay for a weekend of kayaking on the Chester River. We’ll be back!
Stayed 2 nights in Sep 2026
Response from VrboOwner on Sep 21, 2026
Thanks Robert, we're glad you enjoyed the stay. We look forward to having y'all back!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very good location and the place was really niceNeeds a little TLC but that was not a problemwould rent again
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

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

weekend stay

Excellent house, lots of space, clean, comfortable, tons of towels and toiletries, easy walk to town!
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent property with an attentive host. Great value for the price. Small hiccup with WiFi that the host sorted out in less than five minutes.Great accommodations and even more charming town than we expected.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Sparkling clean and centrally located. The check-in process and communication was excellent!
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

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

Fantastic weekend

We rented for my daughter’s graduation from Washington college. Wonderful home that was decorated great with a perfect location!!!
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

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

Perfect!

We had a great weekend stay in this sweet home. It was clean and well provisioned. The owners communicated very well. Beautiful neighborhood and easy walk to restaurants and shops. Don’t miss the Saturday farmers market.
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

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

Wonderful Stay at Portside Manor

The location and home were perfect for a weeklong vacation with my wife and two daughters (ages 13 and 10). Easy walking to restaurants, especially ice cream! Lots of days visiting the community pool 10 minutes away, followed by using the grill in the backyard, walking down Main Street shops, and evening board games. Even drove into Washington DC for a day trip of sightseeing. Home was perfect for our family and we would visit again. Communication with the owner was great, and we really enjoyed the visit.
Stayed 7 nights in Jun 2024
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