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Entire home

Circa 1900 Home in the Heart of Historic Downtown Chestertown

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

Front Porch
Living Room/Dining Room
Dining Room
Family Room
Kitchen

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
4 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill
  • Fenced yard

Explore the area

View in a map
Chestertown, MD
  • Place, Historical Society of Kent County Maryland
    ‪2 min walk‬
  • Place, Chestertown Historic District
    ‪3 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

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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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 2266630vb
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

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 Larrabee Arts Center 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
  • Garfield Center for the Arts at the Prince Theater - 3 min walk - 0.3 km
  • River Arts Chestertown - 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

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

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 River Arts Chestertown are also within 10 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. 82 out of 82 reviews
Rating 8 - Good. 0 out of 82 reviews
Rating 6 - Okay. 0 out of 82 reviews
Rating 4 - Poor. 0 out of 82 reviews
Rating 2 - Terrible. 0 out of 82 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Leah f.

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

10/10 Excellent

Judy S.

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

10/10 Excellent

Thomas G.

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

10/10 Excellent

susan s.

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

10/10 Excellent

Michael H.

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

10/10 Excellent

Darren H.

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

10/10 Excellent

Alison C.

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

10/10 Excellent

Gary N.

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

10/10 Excellent

Deborah K.

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

10/10 Excellent

Mary D.

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

10/10 Excellent

Maya L.

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

10/10 Excellent

Darren H.

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

10/10 Excellent

Lora D.

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

10/10 Excellent

Tricia L.

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

10/10 Excellent

James T.

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

10/10 Excellent

Christopher P.

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

10/10 Excellent

Verified traveller

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

Perfect

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

10/10 Excellent

David F.

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

Downrigging Festival

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

10/10 Excellent

Nicole N.

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

10/10 Excellent

Bethany M.

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

10/10 Excellent

Chris C.

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

Great location, very comfy house

Lovely restored home on a very nice street in the heart of Chestertown. Comfy beds, loved the front porch. Cool coffee station! We had everything we needed, we really enjoyed our week's stay. Thank you to the owner for responding so promptly and resolving the problem with one of the shower faucets, really appreciated that.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Sallie S.

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

10/10 Excellent

Cheryl S.

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
Verified

10/10 Excellent

chris r.

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

10/10 Excellent

Vijay S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Property was as described in the listing!! Very clean and well appointed with toiletries, towels, dishes, etc.Very clean, safe, quiet neighborhood.Enjoyed walking to the farmer's market, Evergrain Bread Company, and waterfront area.I would highly recommend if you're able to navigate the stairs!
Stayed 3 nights in May 2025

About the host

Hosted by Michelle S.

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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