Entire home

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 living room with a sofa, armchairs, a coffee table, and a staircase.
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.

Reviews

10 out of 10
Exceptional

Highlights

  • Top-rated comfy beds
    Guests liked the comfy beds here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Washington College

Popular amenities

  • Porch or veranda
  • Barbecue
  • Free Wi-Fi
  • Air-conditioning
  • Kitchen
  • Refrigerator

Explore the area

View 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

Rooms & beds

4 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 King Bed

Bedroom 4

1 Double Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

Add dates for prices

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  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, (118 reviews)
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About the area

Chestertown

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.
View more Holiday homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • 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
  • Washington College - 8 min walk - 0.7 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 does it cost to stay at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

As of 9 Nov 2026, prices found for a 1-night stay for 2 adults at Circa 1900 Home in the Heart of Historic Downtown Chestertown on 16 Nov 2026 start from AU$1,111, 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 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.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely loved our stay in this beautiful home! Everything was perfect.
Stayed 3 nights in Oct 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
A lovely older home. Plenty of appliances. Stocked with spices an everything you need for cooking. Updated nice stove. Fenced backyard with fire pit. Walking distance to downtown and the waterfront area. Responsive host. Would definitely stay again.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at this property while in town for a wedding. The house was clean, comfortable, and well stocked with everything we needed (including snacks for a quick pick-me-up between wedding festivities!). The house is located in a peaceful and friendly neighborhood. As three senior adults, we enjoyed the easy stroll to the waterfront and to the farmer's market and eateries on High Street. The host was also very accommodating with our travel schedule. Excellent in every way!
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property in the heart of chestertown. This place is close to everything, the bakery, modern Stone Age, Zelda’s and Washington college. The house is large, clean and super well stocked. This might be the most well stocked property, we have stayed at. Pros- beds were nice and large - multiple bedrooms - great front porch- location Cons- window units only, but wasn’t a big con. Overall I would stay here again and you should consider it too
Stayed 2 nights in Sep 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
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
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
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
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
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