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Circa 1900 Home in the Heart of Historic Downtown Chestertown

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A modern kitchen with white cabinetry, a stainless steel refrigerator, a round dining table with two chairs, and a herringbone floor pattern.
A living room with a fireplace, a ceiling fan, and a large window with a view of a mountain landscape.
A modern kitchen with white cabinetry, a herringbone wood floor, a gas stove, and a dishwasher.
A living room with a sofa, armchairs, a coffee table, and a staircase.
A kitchen with white wooden walls, a window with a view of a brick building, and a wooden cabinet with a coffee maker and kitchen utensils.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View 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

Room options

About the area

Chestertown

This holiday home puts you in the heart of Chestertown, within steps of Historical Society of Kent County Maryland and Chestertown Historic District. Highlights at this holiday home include a kitchen, a washing machine and free WiFi. .Home features 2 bathrooms, a patio and a living room. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A fenced private garden, a TV and a coffee/tea maker are also available. .This smoke-free holiday home offers a garden and barbecues. Additionally, you'll find laundry facilities. .Sights within a 15-minute walk of this Chestertown holiday home include Garfield Center for the Arts at the Prince Theater and Sumner Hall.
View more Holiday homes in ChestertownOpens in a new window

What's nearby

  • Historical Society of Kent County Maryland - 2 min walk - 0.2 km
  • Chestertown Historic District - 3 min walk - 0.3 km
  • Wilmer Park - 6 min walk - 0.6 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

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

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

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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4.0 out of 5, 107, 107 reviews
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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

Information provided by the property may be translated using automated translation tools

Pets

  • No pets 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher and a smoke detector in all accommodation.

Frequently asked questions

Are there any beaches close to Circa 1900 Home in the Heart of Historic Downtown Chestertown?

The closest beach to Circa 1900 Home in the Heart of Historic Downtown Chestertown is Betterton Beach (18 km).

Does Circa 1900 Home in the Heart of Historic Downtown Chestertown have a pool?

No, this holiday home doesn't have a pool.

Is there a free airport shuttle available at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

No, Circa 1900 Home in the Heart of Historic Downtown Chestertown does not offer an airport shuttle service.

What time are check-in & check-out at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

Check-in begins at 3:00 PM. Check-out time is 11:00 AM.

Are pets allowed at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

No, pets are not allowed.

Circa 1900 Home in the Heart of Historic Downtown Chestertown Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 89 out of 89 reviews
Rating 8 - Good. 0 out of 89 reviews
Rating 6 - Okay. 0 out of 89 reviews
Rating 4 - Poor. 0 out of 89 reviews
Rating 2 - Terrible. 0 out of 89 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Bill D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was wonderful. Very well stocked, great location. Absolutely perfect. Thank you!
Stayed 2 nights in Jun 2026
Verified review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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