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Circa 1900 Home in the Heart of Historic Downtown Chestertown

Photo gallery for Circa 1900 Home in the Heart of Historic Downtown Chestertown

A modern kitchen with white cabinetry, a stainless steel refrigerator, a round dining table with two chairs, and a herringbone floor pattern. - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)
A modern kitchen with white cabinetry, a herringbone wood floor, a gas stove, and a dishwasher. - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)
A living room with a sofa, armchairs, a coffee table, and a staircase. - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)
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. - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)
A living room with a fireplace, a ceiling fan, and a large window with a view of a mountain landscape. - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)
You can look forward to a firepit, a garden and laundry facilities at Circa 1900 Home in the Heart of Historic Downtown Chestertown. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

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About this property

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.

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About the area

Located in Chestertown, this holiday home is in the city centre. 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. Take the opportunity to explore the area for water adventures such as fishing and other activities like birdwatching. Visit our Chestertown travel guide
View more Holiday homes in Chestertown
Map
Chestertown, MD

What's nearby

  • A field of soybeans with a barn and silos in the background.
    Washington College
    8 min walk - 0.7 km
  • Historical Society of Kent County Maryland
    2 min walk - 0.2 km
  • Chestertown Historic District
    3 min walk - 0.3 km
  • River Arts Chestertown
    6 min walk - 0.6 km
  • Sumner Hall
    6 min walk - 0.6 km

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

Frequently asked questions

Is Circa 1900 Home in the Heart of Historic Downtown Chestertown pet-friendly?

No, pets are not allowed at this property.

How much is parking at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

On-site parking is available at the property.

What time is check-in at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

Check-in begins at 3:00 PM.

What time is check-out at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

Checkout is at 11:00 AM.

Where is Circa 1900 Home in the Heart of Historic Downtown Chestertown located?

Located in the heart of Chestertown, this holiday home is steps away 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.

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Reviews

Circa 1900 Home in the Heart of Historic Downtown Chestertown Reviews

10

Exceptional

10

Cleanliness

10

Location
Rating 10 - Excellent. 93 out of 93 reviews
Rating 8 - Good. 0 out of 93 reviews
Rating 6 - Okay. 0 out of 93 reviews
Rating 4 - Poor. 0 out of 93 reviews
Rating 2 - Terrible. 0 out of 93 reviews

Reviews

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
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
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

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

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

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

Great spot

Great spot and location! Everything we needed was already there. Thank you!
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

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

Fabulous Chestertown

What a wonderful vrbo. Centrally located, charming historic home that was renovated. Really felt like “home”. So much so that the family decided that we’d like to make it an annual tradition
Stayed 7 nights in Jul 2023
Verified review

10/10 Excellent

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

Lovely getaway

This is a lovely home on a beautiful garden lined street. We were within walking distance of restaurants, coffee shops and even Chestertown’s Saturday morning market. The home is well maintained and appointed with thoughtful touches that made our stay relaxing and enjoyable. My husband and I will be staying here again.
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

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

Girls weekend

Michelle was absolutely wonderful to deal with, and her place is just lovely. It was spotless when we arrived and had absolutely everything we needed for a comfortable weekend. The location is great. We will be back.
Stayed 4 nights in Nov 2023
Verified review

10/10 Excellent

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

Perfect!

This is the cutest place! Super clean and equipped to the max, everything we could possibly need was provided. The beds/linens are extremely comfortable. And our hostess was quick to respond to a problem with the heat. Highly recommend!
Stayed 4 nights in Jan 2025
Verified review

10/10 Excellent

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

Charming Visit

My 3 friends and I thoroughly enjoyed our stay. We loved the house and felt totally comfortable. We enjoyed walking downtown and taking in the colors, sounds, food and people at the Farmers Market. Hopefully, my granddaughter will continue to attend WAC to give me a good reason to visit often. I will return to Queen St.
Stayed 2 nights in Nov 2023
Verified review

10/10 Excellent

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

Wonderful home in Chestertown

We rented four bedroom home in Chestertown for graduation weekend. Home has everything you could possibly need. All bedrooms are upstairs with one bathroom and one bathroom on lower level. If you have any elderly members of your party, this may be
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

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

A week in living history -Chestertown, Ms

The house we rented resided on Queen Street, an historical street near the Chester River. It provided our family with welcoming spaces to chat, dine and watch shows as well as four comfortable bedrooms to sleep peacefully at night. We walked to nearby shops and a farmer market, all charming. The people are friendly and helpful. One senses a true feeling of commnity! We will return for another vacation in this lovely town well preserved and charming!
Stayed 7 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Ideally situated. Close to town and restaurants. Spacious rooms. Plentiful towels. Well stocked supplies. Thank you.
Stayed 2 nights in Jun 2026
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
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
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

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