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Circa 1900 Home in the Heart of Historic Downtown Chestertown

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A modern kitchen with white cabinetry, a stainless steel refrigerator, a round dining table with two chairs, and a herringbone floor pattern.
A modern kitchen with white cabinetry, a herringbone wood floor, a gas stove, and a dishwasher.
A kitchen with white wooden walls, a window with a view of a brick building, and a wooden cabinet with a coffee maker and kitchen utensils.
A living room with a fireplace, a ceiling fan, and a large window with a view of a mountain landscape.
A living room with a sofa, armchairs, a coffee table, and a staircase.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Explore the area

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

Room options

Similar properties

A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
Comfort Inn & Suites Chestertown
Chestertown
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
4.3 out of 5, Excellent, 993 reviews
$98 nightly
The price is $109
Nov 15 - Nov 16
Total with taxes and fees
Comfort Inn & Suites Chestertown

About the neighborhood

Chestertown

A stay at this vacation home places you in the heart of Chestertown, steps from Historical Society of Kent County Maryland and Chestertown Historic District. .This vacation home is 9.8 mi (15.8 km) from Chesapeake Bay and 0.1 mi (0.2 km) from Garfield Center for the Arts at the Prince Theater.
View more Vacation Homes in ChestertownOpens in a new window

What's nearby

  • Historical Society of Kent County Maryland - 2 min walk - 0.1 miles
  • Chestertown Historic District - 3 min walk - 0.2 miles
  • River Arts Chestertown - 6 min walk - 0.4 miles
  • Sumner Hall - 6 min walk - 0.4 miles
  • Washington College - 8 min walk - 0.4 miles

Getting around

  • Baltimore, MD (MTN-Martin State) - 104 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

About this property

Entire place

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

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Beautiful 1900 built home that has all of its historic charm while having updated amenities. Enjoy everything historic Chestertown has to offer as the house is walking distance to the shops, restaurants, Chester River Waterfront, and year round Saturday farmers market. Located on a one way street that is flanked with beautiful historic homes and free on street parking. For those with boats, the home is a short walk to the Chestertown Marina which has a boat ramp and transient slips. Our home is only 2.6 miles from Brittland Manor. Please note there is a ring camera by the front door for security purposes.
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private patio. Complimentary wireless internet access is available to keep you connected. Conveniences include a desk and a microwave.
Take in the views from a garden and make use of amenities such as barbecue grills.
Guests will find features like internet access and onsite parking.

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

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

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • Games
  • TV

Outdoor areas

  • Barbecue grill
  • Fenced yard
  • Firepit
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near the marina

Things to do

  • Birdwatching nearby
  • Fishing nearby

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

General

  • Garden

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

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 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

Circa 1900 Home in the Heart of Historic Downtown Chestertown Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 91 out of 91 reviews
Rating 8 - Good. 0 out of 91 reviews
Rating 6 - Okay. 0 out of 91 reviews
Rating 4 - Poor. 0 out of 91 reviews
Rating 2 - Terrible. 0 out of 91 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property!
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was wonderful. Very well stocked, great location. Absolutely perfect. Thank you!
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Location and nice house!
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was great. Beds were very comfortable and the location was great.
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We love the location which is just steps away from the High Street. Very comfortable beds and very thoughtfully equipped.
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house, will stay again in the future.
Stayed 3 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful house! This is a well equipped and cared for home. I highly recommend this spot.
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely, comfortable house in a prime location in historic Chestertown. Ladies weekend away- we enjoyed drinks on the porch, dinner out back and walking to the Farmers Market. Well- stocked kitchen, comfortable beds, and lots of comfy blankets downstairs making it a cozy stay. Overall a lovely charming home in an A location!
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful home in ideal location. We parked the car on arrival and walked everywhere. House is spacious and very well equipped and welcoming.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

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

Beautifully renovated historic property on quiet street, walking distance to shops and restaurants

We had a wonderful stay at this property!
Stayed 2 nights in Mar 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had another wonderful stay at the Circa 1900 home in Chestertown. The location is perfect for shopping in the downtown area. Everything about staying in this home is easy and enjoyable!
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely stay at the property which was central to everything, and we had a fun time walking around Chestertown. We were there during the two hottest days in July, and the house stayed a comfortable temperature the whole time. Love the special touch of the candies and snacks. Thank you
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

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

Small town trip.

Enjoyed the stay and house very comfortable.
Stayed 5 nights in Aug 2024
Verified review

10/10 Excellent

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

Everything you could need in perfect location

The property is charming, clean, well-equipped, and located steps to the farmers' market and downtown shops. We would definitely stay again.
Stayed 3 nights in Aug 2023
Verified review

10/10 Excellent

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

Fall weekend

Lovely, well kept and tastefully furnished house in a great location.
Stayed 2 nights in Oct 2024
Verified review

10/10 Excellent

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

Great Stay for Summer Weekend in Chestertown

Michelle's home was perfect for our group (two couples with kids) to stay for a weekend in Chestertown attending a wedding. Home was clean and well appointed for our stay, right downtown for easy walking distance to food and shopping options. Would definitely stay here again during another trip to the area, thank you!
Stayed 3 nights in Jul 2022
Verified review

10/10 Excellent

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

Go-To Place in Chestertown

We've stayed here twice now and always enjoy it. It's very comfortable and is near everything. Will definitely return.
Stayed 7 nights in Dec 2023
Verified review

10/10 Excellent

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

Perfect

Great house, location and host!
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This lovely home was adorable! Very clean and cozy. A very comfortable space. It was also in a great location. Only a five minute walk to the Main Street. We went to the farmer’s market Saturday morning and a cute cafe for breakfast. Would definitely stay here again.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

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

Downrigging Festival

We enjoyed everything about the property.
Stayed 4 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is exactly as advertised. It is well stocked and it’s clear the host has put a lot of thought into making the house comfortable for folks. Host was also very quick to respond. Chestertown is lovely and this house is in the perfect location. Will stay here again!
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

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

Girls Trip

Great space. Cozy fireplace. Well appointed house. Perfect location, we walked everywhere.
Stayed 2 nights in Dec 2024
Verified review

10/10 Excellent

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

Chestertown

House was in a great location and very well appointed. We had everything we needed. Would highly recommend.
Stayed 3 nights in Mar 2025
Verified review

10/10 Excellent

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

Well decorated comfortable home in a great location

The home is on a beautiful street in downtown Chestertown that is walkable to restaurants, stores, and the Saturdays farmers market. Each room is well decorated and stocked for a comfortable stay. We enjoyed the backyard with spring flowers in bloom. We would highly recommend this home!
Stayed 2 nights in Apr 2025
Verified review

10/10 Excellent

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

Felt Like Home

The property was exactly as described and felt like home, and property manager was gracious and accommodating. The amenities were thoughtfully selected and appreciated. I will definitely stay here when I return to the area.
Stayed 5 nights in Jul 2023