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Circa 1900 Home in the Heart of Historic Downtown Chestertown

Top rated by guests
Front Porch
Family Room
Kitchen
Kitchen
Kitchen
review stars
10Outstanding
(86 Ratings)
"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!"
Alison C.
Don't miss out! Price and availability may change
10 / 10
Outstanding(86 Ratings)

House in Chestertown, MD

6 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

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.

Amenities at Circa 1900 Home in the Heart of Historic Downtown Chestertown

Non-smoking
No pets allowed
Family friendly

Map of Chestertown, MD

city location on map

Nearby attractions

National Aquarium
29.6 mi
M&T Bank Stadium
30.3 mi
The Walters Art Museum
30.2 mi
Fort McHenry National Monument and Historic Shrine
27.9 mi

Ratings and reviews

10 / 10
Outstanding(86 Ratings)
10 / 10Outstanding·Dec 2025
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!
10 / 10Outstanding·Nov 2025
Everything was great. Beds were very comfortable and the location was great.
10 / 10Outstanding·Oct 2025
We love the location which is just steps away from the High Street. Very comfortable beds and very thoughtfully equipped.
10 / 10Outstanding·Oct 2025
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.
$$$$
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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Circa 1900 Home in the Heart of Historic Downtown Chestertown. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.