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Circa 1900 Home in the Heart of Historic Downtown Chestertown

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Fridge, microwave, oven, stovetop
Combined shower/tub, hair dryer, towels, soap
4 bedrooms, desk, iron/ironing board, free WiFi
Property grounds
Aerial view

Reviews

10 out of 10

Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Parking available
    Parking available
  • Outdoor Space
    Outdoor Space
  • Washer
    Washer
  • Barbecue grill
    Barbecue grill
  • Free WiFi
    Free WiFi
  • Kitchen
    Kitchen

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Circa 1900 Home in the Heart of Historic Downtown Chestertown

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.

Property manager

Michelle S.

Languages

English

Property amenities

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Cookware/dishes/utensils
  • Paper towels
  • Toaster
  • Electric kettle

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bed sheets provided

Bathrooms

  • 2 bathrooms
  • Shower/tub combination
  • Toilet paper
  • Towels provided
  • Soap
  • Hair dryer
  • Shampoo

Living spaces

  • Living room

Entertainment

  • TV
  • Books
  • Games

Outdoor areas

  • Patio
  • Fenced yard
  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Firepit

Laundry

  • Washing machine and dryer
  • Near laundromat

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a health or beauty spa
  • Near a hospital
  • In a village

Things to do

  • Fitness facilities nearby
  • Marina nearby
  • Birdwatching nearby
  • Fishing nearby

Safety features

  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

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Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the neighborhood

Map
Chestertown, MD

What's nearby

  • Historical Society of Kent County Maryland - 1 min walk
  • Garfield Center for the Arts at the Prince Theater - 2 min walk
  • River Arts Chestertown - 6 min walk
  • Washington College - 8 min walk
  • Rolphs Wharf Marina - 10 min drive

Getting around

  • Baltimore, MD (MTN-Martin State) - 104 min drive

Restaurants

  • ‪McDonald's - ‬4 min drive
  • ‪Dining Hall - ‬18 min walk
  • ‪Procolino Pizza - ‬2 min drive
  • ‪China House - ‬2 min drive
  • ‪The Freeze - ‬2 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.

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?

Check-out is at 11:00 AM.

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

Set in the center of Chestertown, this family-friendly vacation home is 0.5 mi (0.8 km) from Washington College, and within 16 mi (25 km) of Betterton Beach and Rock Hall Harbor. Queenstown Premium Outlets and Eastern Neck National Wildlife Refuge are also within 25 mi (40 km).

Circa 1900 Home in the Heart of Historic Downtown Chestertown Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 62 out of 62 reviews" "
Rating 8 - Good. 0 out of 62 reviews" "
Rating 6 - Okay. 0 out of 62 reviews" "
Rating 4 - Poor. 0 out of 62 reviews" "
Rating 2 - Terrible. 0 out of 62 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

Justin s.

Liked: Cleanliness
Stayed 4 nights in Aug 2024

10/10 Excellent

Mary D.

Liked: Cleanliness
Small town trip.
Enjoyed the stay and house very comfortable.
Stayed 5 nights in Aug 2024

10/10 Excellent

Suzi A., Blacksburg, VA USA

Liked: Cleanliness
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

10/10 Excellent

Diane P., Lancaster

Liked: Cleanliness
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

10/10 Excellent

Christopher P.

Liked: Cleanliness
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

10/10 Excellent

Pam S.

Liked: Cleanliness
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

10/10 Excellent

Terrie S.

Liked: Cleanliness
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

10/10 Excellent

chris r.

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

10/10 Excellent

Verified traveler

Liked: Cleanliness
Perfect
Great house, location and host!
Stayed 3 nights in Sep 2023

10/10 Excellent

Tricia L., Washington, DC, USA

Liked: Cleanliness
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

10/10 Excellent

Arianna G.

Liked: Cleanliness
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

10/10 Excellent

Alisa R.

Liked: Cleanliness
Enjoyed this updated home
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.
Stayed 6 nights in Jul 2023

10/10 Excellent

Cheryl S.

Liked: Cleanliness
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

10/10 Excellent

Nora M.

Liked: Cleanliness
Perfect!
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.
Stayed 7 nights in Jun 2023

10/10 Excellent

Nancy M., Morristown, NJ

Liked: Cleanliness
Fantastic Getaway Stay
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!!!
Stayed 6 nights in Jun 2023

10/10 Excellent

Elizabeth H.

Liked: Cleanliness
Fantastic Property
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.
Stayed 4 nights in May 2023

10/10 Excellent

Deborah K.

Liked: Cleanliness
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

10/10 Excellent

Naked S.

Liked: Cleanliness
Chestertown
Well appointed, everything you could want was there. Wish there had been regular cable however.
Stayed 2 nights in Jan 2023

10/10 Excellent

Nina V., Libertyville, Illinois

Liked: Cleanliness
Charming home in walk to town location!
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.
Stayed 3 nights in Dec 2022

10/10 Excellent

Deborah M.

Liked: Cleanliness
Beautiful Chestertown
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
Stayed 9 nights in Dec 2022

10/10 Excellent

Chris P., Sausalito, CA, USA

Liked: Cleanliness
Can't beat the location
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.
Stayed 3 nights in Nov 2022

10/10 Excellent

Jodi R.

Liked: Cleanliness
Wonderful home!
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!
Stayed 2 nights in Nov 2022

10/10 Excellent

Christine K.

Liked: Cleanliness
The Most Amazing House!
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!!
Stayed 4 nights in Nov 2022

10/10 Excellent

Ann H., Philadelphia PA

Liked: Cleanliness
Awesome stay during Downrigger Weekend
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.
Stayed 3 nights in Oct 2022

10/10 Excellent

Jennifer P.

Liked: Cleanliness
Visit with family
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.
Stayed 3 nights in Oct 2022