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

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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 two-story house with a porch, a flag, and a small garden area.
A dining room with a wooden table, chairs, and a ship model.
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 living room with a sofa, coffee table, and fireplace.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 8

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space
  • Parking available

Explore the area

View in a map
Chestertown, MD
  • Place, Historical Society of Kent County Maryland
    ‪1 min walk‬
  • Place, Chestertown Historic District
    ‪2 min walk‬
  • Place, Washington College
    ‪9 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪126 min drive‬

Room options

About the neighborhood

Chestertown

This vacation home places you next to Historical Society of Kent County Maryland and Chestertown Historic District. The vacation home includes a kitchen, a fireplace, and a patio.
View more Vacation Homes in ChestertownOpens in a new window

What's nearby

  • Historical Society of Kent County Maryland - 1 min walk - 0.0 miles
  • Chestertown Historic District - 2 min walk - 0.1 miles
  • River Arts Chestertown - 5 min walk - 0.3 miles
  • Wilmer Park - 5 min walk - 0.3 miles
  • Washington College - 9 min walk - 0.5 miles

Getting around

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

Restaurants

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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


Welcome to our charming Chestertown Home! This beautiful house offers a comfortable and inviting space for your stay. With two full bedrooms and bathrooms on the second floor and a cozy third-floor retreat with two twin beds, there is plenty of room for everyone.

Conveniently located behind the house, you will find three reserved off-street parking spaces. Upon entering the back gate, you'll enter a tranquil courtyard perfect for a barbecue. The screened-in porch leads directly to the well-equipped kitchen, with all the essentials and appliances you need to prepare home-cooked meals.

Adjacent to the kitchen, you'll discover two separate relaxation areas, each providing a cozy atmosphere to unwind. A full bathroom is also conveniently located nearby. On the backside of the house is a dining room/living room with a television, offering access to popular streaming services like Netflix, Hulu, and Disney+.

On the other side of the kitchen, you'll find another inviting living room featuring a gas fireplace, creating a warm and cozy ambiance. You'll find the entryway and front door at the end of this living room. Step outside onto the lovely porch, where you can enjoy your morning coffee or evening drinks while taking in the surroundings.

Head up the wooden stairway to the second floor, where you'll discover two spacious bedrooms, each with its full bathroom for added convenience. The third floor offers a peaceful retreat with two twin beds for those traveling with children or additional guests.

We invite you to make yourself at home. Experience comfort, convenience, and a relaxing atmosphere during your stay.
The vacation home is air-conditioned and features a kitchen, 3 bathrooms, and a patio, and there's space to spread out with 3 bedrooms. Other standard amenities include a washing machine, a fireplace, and a coffee maker.

Similar properties

Exterior
Guest Suite for up to 2 in a Victorian on the Chester River
Millington
  • Free WiFi
  • Air conditioning
  • Parking available
  • Water view
9.8 out of 10, Exceptional, 27 reviews
$118 nightly
The price is $125
Sep 10 - Sep 11
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River

Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Wheelchair-accessible parking available
  • Onsite parking includes off-street options

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Smart TV
  • Video games

Outdoor areas

  • Barbecue grill
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Computer monitor
  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 1"on-site accessible parking spaces 1", on-site accessible parking spaces
  • Wheelchair-accessible parking
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

Policies

Check-in

Minimum check-in age: 28

Check-out

Flexible check-out available (contact host to arrange)

Special check-in instructions

The front desk hours vary at this property
Guests must contact the property for check-in information
To make arrangements for check-in please contact the property ahead of time using the information on the booking confirmation
You will receive an email from the host with check-in and check-out instructions
Check-out time is flexible; to make arrangements, please contact the property ahead of time using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.

Frequently asked questions

What's there to see near this vacation home?

This vacation home is located in Chestertown, just steps from Historical Society of Kent County Maryland and Chestertown Historic District, and within a short walk of Wilmer Park. You'll also find Kings Town Park and Garfield Center for the Arts at the Prince Theater less than a mile away.

Is parking available on site at The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown?

No, there isn't parking at this vacation home.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What do couples enjoy most about The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown?

Amenities that appeal to couples at this vacation home include a fireplace, a kitchen, and a smart TV.

Are there hot tubs at The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown?

No, this vacation home doesn't have a spa tub.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Are there connecting rooms at The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown?

No, this vacation home doesn't feature connecting guestrooms.

Where is the closest airport to this vacation home?

The closest major airport to this vacation home is Baltimore, MD (MTN-Martin State), which is about 20.8 mi away. Another top airport is Easton, MD (ESN-Easton - Newnam), which is around 27.5 mi away.

Are there rooms with balconies that I can book at The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown?

Yes, every house at The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown comes with a patio.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 6 out of 6 reviews
Rating 8 - Good. 0 out of 6 reviews
Rating 6 - Okay. 0 out of 6 reviews
Rating 4 - Poor. 0 out of 6 reviews
Rating 2 - Terrible. 0 out of 6 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Jim G.

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

Lisa G.

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

April D.

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

Krista K.

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

Dorothy B.

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

Zachary G.

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