Circa 1900 Home in the Heart of Historic Downtown Chestertown
House in Chestertown, MD
6 guests · 4 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
High-end valuePrice for this property is higher than average in the area
About this house rental
Beautiful1900 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
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden
Family friendly
Map of Chestertown, MD
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Ratings and reviews
5.0 / 5.0
Enjoyed the stay and house very comfortable.
5.0 / 5.0
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!
5.0 / 5.0
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.
5.0 / 5.0
We've stayed here twice now and always enjoy it. It's very comfortable and is near everything. Will definitely return.
5.0 / 5.0
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.
5.0 / 5.0
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.
5.0 / 5.0
Great spot and location! Everything we needed was already there. Thank you!
5.0 / 5.0
Great house, location and host!
5.0 / 5.0
The property is charming, clean, well-equipped, and located steps to the farmers' market and downtown shops. We would definitely stay again.
5.0 / 5.0
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
5.0 / 5.0
This home was nicely decorated with everything well thought out by the owner. Well appointed and clean design aesthetic. Loved the walk in closet; don’t even have that at home. Great to be able to walk to the small downtown area. Very welcoming. Would definitely rent again.
5.0 / 5.0
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.
5.0 / 5.0
Even tough this place was a bit larger than needed for just my husband and myself, its proximity to town, accompanied by its having everything you could possibly need or desire, makes it the ideal place for everyone and anyone to stay. Michelle could not have been more helpful, and had every amenity needed (basic office supplies in the drawers, little snacks and candies, roku, toiletry supplies). Everything!!! I also happened to lose an earring, which she found in the dishwasher of all places and promptly mailed back to me without charging me to do so. I would absolutely stay here again!!!
5.0 / 5.0
We stayed a week at this fantastic house. Everything needed was provided. The host was available if needed (we didn’t - she had thought of everything). The house is spacious and clean, and walking distance to so many good restaurants, cafes, a theater, and so much more. We were sad to leave and hope to be back.
5.0 / 5.0
Wonderful location in Chestertown! We were at the house for graduation weekend. Centrally located to everything. Property was outstanding. Everything was prepped for the guests, including a candy jar! Thank you for such a memorable place to wrap up our time at Washington College.
5.0 / 5.0
We had a wonderful stay at this property!
5.0 / 5.0
Well appointed, everything you could want was there. Wish there had been regular cable however.
5.0 / 5.0
Our family loved staying in this charming home in a perfect location to enjoy Chestertown! We walked to restaurants and shops and never needed to drive during our stay.
We appreciated the wine, treats, coffee ,and other amenities the host had available for us .
If we travel to Chestertown again we would love to book another stay.
5.0 / 5.0
We loved staying at this beautiful property. Everything was thought of, from basic necessities of dishwasher tablets to laundry supplies, to little treats in the kitchen. The decor is gorgeous. Chestertown itself is a quick walk down the street, with a great bakery, several cafés and boutiques, and a Farmers Market on Saturday morning. We highly recommend this property. Debbie & Robert, Jo & Peter from New Zealand and Australia
5.0 / 5.0
If you're staying in Chestertown, this is the best place. It's near everything. The home is beautifully furnished and well-equipped. Will definitely come back.
5.0 / 5.0
The house was great - beautifully decorated and had everything we could need for our short weekend stay. The host was very kind and went above and beyond with little touches to enhance the stay (snacks and toiletries availble, if needed). Thank you!
5.0 / 5.0
This was my all time favorite house I've ever rented! It was on a charming street, the house was an old Colonial beautifully kept house decorated perfectly. The bedding was so comfy, the house was equipped with a great kitchen, living room furnture was beautiful and comfy. It was the most thoughtfully laid out house. The owner was always available if we had a question, and so generous with her suggestions on where to visit. She even left me a bottlle of wine when we arrived for my birthday trip. I can't rave about our experience any more, it was just the absolute best, we all want to come back very soon!!! Thank you so much Michelle!!
5.0 / 5.0
Michelle has done a fabulous job with an incredible house. Really wonderful stay and we appreciated all of the little touches – from the bottle of wine and snacks to the bathroom amenities to the original artwork and charger stations. Extremely comfortable beds , lovely backyard with a grill and great grill tools, very well equipped kitchen. Amazing little touches everywhere. Really easy walk to town and the waterfront. One of the best rental experiences we’ve had!! And Downrigger Weekend is a great time to visit. Thanks Michelle.
5.0 / 5.0
Absolutely loved our stay in this amazing house. The house was easy to find and just perfect for us! We enjoyed the farmers market downtown on Saturday and sitting outside in the backyard enjoying the sunshine and the fire pit in the evening. Will be planning another visit to see family next year and hope to stay here again.
5.0 / 5.0
This is a wonderful house, larger than it looks from outside. Open and airy and decorated in nice contemporary tasteful way. Very well supplied in kitchen, bath, and bedrooms with anything you might possibly need. On one of Chestertown’s most charming streets. Communication with owner was super easy. Recommended for sure!
5.0 / 5.0
This property is a hidden gem! The decor is perfection. We were in town for a wedding and it checked off all the boxes that we needed for our stay. The six of us had plenty of space to spread out. The rooms were quite large! Highly suggest booking this listing for your future stay in downtown Chestertown!
5.0 / 5.0
Great place, - clean, quiet, comfortable. Well equipped. Breakfast in the backyard w croissants from the bakery a block away - nice way to start the day!
5.0 / 5.0
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!
5.0 / 5.0
The prettiest street in the heart of Chestertown
Our second stay at this gem and it did not disappoint. One of the best appointed and furnished rentals I have ever stayed in. A short one block walk to the heart of Chestertown with its charming shops, restaurants, parks, Saturday Farmers Market, and the hub of festivals. The beds are comfy, the bathrooms clean and well-appointed, the kitchen is quite large and very functional and the gathering spaces large and well-furnished. Loved sitting on the front porch with my coffee exchanging pleasantries with the neighbors. If available for your stay, grab it!
5.0 / 5.0
Chestertown
Very well maintained home with all the comforts of home. Nice thick towels and comfy beds. Very well appointed.
5.0 / 5.0
Wonderful stay in Chestertown MD
This house far exceeded our expectations! It was comfortable, spacious and beautifully decorated! The owners thought of everything … fully stocked coffee nook, plenty of paper and cleaning products, lots of tech chargers strategically placed, etc! We hope to return one day soon!!!
5.0 / 5.0
Wonderful Stay!
We enjoyed our 3 night stay so much! The house is charming, very spacious, and beautifully decorated. Loved sitting on the front porch swing! Michelle has outfitted the home with everything you could need and then some…like the jar of candies and a welcome bottle of wine. It was great waking up and walking to the end of the street to get coffee and pastries at Evergrain…such a convenient location right in town amidst all the shops and restaurants…we will definitely be coming back!
5.0 / 5.0
Perfect for the occasion
Great accommodations for our family to relax and enjoy the graduation festivities at Washington College. The house was well appointed including a patio so we could hang and cook instead of worrying about finding restaurant for our celebration. This home was only a quick 3 block walk to the charming shops, on the town square. If we have a chance to go back, I’d definitely look at this great rental.
5.0 / 5.0
We would love to return to same home
My family and I traveled for my niece’s wedding and stayed in this very charming and welcoming home. The place and owner both had an impact on the overall impression of the town and our vacation. We were very pleased with both. Thank you!
5.0 / 5.0
Alumni weekend stay
Absolutely loved staying here! This place was beautiful and exactly what we hoped for.
5.0 / 5.0
Lovely week in Chestertown
This house was perfect for our small family gathering. My sisters and I grew up in Chestertown and we gathered there to surprise my Dad, who still lives there.
This house had everything we needed for a week of spending time together. We cooked large family meals in the well equipped kitchen and barbecued and sat in the sunshine in the backyard. We were easy walking distance to downtown and popped out frequently to get ice cream and look in the shops.
We really liked sitting on the front porch in the afternoon as the sun set and saying Hi to the very friendly people who walked by.
We slept great in the large beds and loved waking up to the birds chirping. You can hardly hear the road down the block at any time of day.
This house was fantastic and we would absolutely stay here again.
5.0 / 5.0
Wonderful Accommodation
Michelle’s house is extremely clean and comfortable. It was the perfect place for a family get together. We loved it.
5.0 / 5.0
Beautiful house/thoughtful touches
Loved the house! Centrally located and nicely decorated. Michelle was a thoughtful host with a lot of extra amenities for her guests — snacks, a bottle of wine, toiletries in case you forgot something. Would definitely come again!
5.0 / 5.0
Comfortable, well appointed home in close proximity to town.
The home was in a great central location. Quiet street. Easy access to great shops and restaurants. Comfortable and spacious spot to call home for a few days! Plenty of amenities in the house, and really nice towels. Thanks for a great stay!
5.0 / 5.0
Great location and house
Beautiful and well appointed house, close to the town and the water. Very accommodating host - we had a great stay!
FAQs
How much does this house cost compared to others in Chestertown?
The average price for a rental in Chestertown is R 3,373 per night. This rental is R 2,728 above the average.
Is parking included with this house?
Yes, parking is listed as an 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 10 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, parking, and laundry.
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