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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

Property grounds
Property grounds
Fridge, microwave, oven, stovetop
Dining
4 bedrooms, desk, iron/ironing board, free WiFi

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Barbecue grill
  • Air conditioning

Add dates for prices

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

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • Games
  • TV

Outdoor areas

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

Laundry

  • Laundry facilities
  • Washing machine

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 a village
  • In the city centre
  • Near a health/beauty spa
  • Near a hospital
  • Near the marina

Things to do

  • Birdwatching nearby
  • Fishing nearby

Safety features

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

General

  • Garden

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

Events

No events allowed

Smoking

Smoking is not permitted

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
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
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 area

Map
Chestertown, MD

What's nearby

  • Historical Society of Kent County Maryland - 2 min walk - 0.2 km
  • Wilmer Park - 6 min walk - 0.6 km
  • River Arts Chestertown - 6 min walk - 0.6 km
  • Washington College - 11 min walk - 1.0 km
  • Rolphs Wharf Marina - 12 min drive - 9.0 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬4 min drive
  • ‪Dining Hall - ‬18 min walk
  • Procolino's
  • ‪China House - ‬2 min drive
  • ‪Subway - ‬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?

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.

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Circa 1900 Home in the Heart of Historic Downtown Chestertown Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 72 out of 72 reviews
Rating 8 - Good. 0 out of 72 reviews
Rating 6 - Okay. 0 out of 72 reviews
Rating 4 - Poor. 0 out of 72 reviews
Rating 2 - Terrible. 0 out of 72 reviews

10/10

Cleanliness

Reviews

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

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

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

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

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

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

10/10 Excellent

Tricia L., Washington, DC, USA

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

10/10 Excellent

amy p.

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

Perfect!

This is the cutest place! Super clean and equipped to the max, everything we could possibly need was provided. The beds/linens are extremely comfortable. And our hostess was quick to respond to a problem with the heat. Highly recommend!
Stayed 4 nights in Jan 2025

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

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

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

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

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

10/10 Excellent

Arianna G.

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

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

Pam S.

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

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

Nina V., Libertyville, Illinois

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

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

Missy P.

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

Lucky to be first renter of home!

We were lucky enough to be the first renter of this home after its complete renovation. Tastefully decorated and relaxing accommodations. Well stocked kitchen and bathroom necessities. Nice for a family of 6 to explore Chestertown.
Stayed 2 nights in May 2021

10/10 Excellent

Naked S.

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

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

Terrie S.

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

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

Suzi A.

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

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

Alisa R.

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

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

Nora M.

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

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

Ann Marie B.

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

My husband's 50th

This home was so adorable and CLEAN! I loved all of her attention to detail. I brought all of this stuff (toilet paper, paper towels, tide pods etc) and she had it all there waiting! and more! We will definitely be back. Thank you!
Stayed 2 nights in Sep 2021

10/10 Excellent

Nancy M., Morristown, NJ

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

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

Stefania P., Arlington

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

A wonderful stay

We traveled as a group of friends to Chestertown to participate in the Rock Hall Triathlon. The house was awesome. Stocked with lots of treats, including a bottle of wine to celebrate! The house was spotlessly clean, well organized, and we had everything we needed in the kitchen, rooms, and bathrooms. The beds and linen were very comfortable and the bathrooms clean and towels soft and enough for all of us. The host was very responsive, kind, and gave us a warm welcome from the moment we booked. Thank you for that. We highly recommend staying in this property. The location very close to the High Street of Chestertown where there are lots of nice shops and a generally great vibe. THANK YOU! Stefania
Stayed 2 nights in Jun 2021