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Circa 1900 Home in the Heart of Historic Downtown Chestertown

Vacation home perfectly located for exploring Chestertown

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

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 6

Popular amenities

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

Explore the area

View in a 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, Easton, MD (ESN-Easton - Newnam)
    ‪46 min drive‬

Room options

About the neighborhood

Chestertown

Heart of Chestertown.With a stay at this Chestertown vacation home, you'll be steps from Historical Society of Kent County Maryland and Chestertown Historic District. Garfield Center for the Arts at the Prince Theater and Sumner Hall are also within half a mile (1 km).
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What's nearby

  • Historical Society of Kent County Maryland - 2 min walk - 0.1 miles
  • Chestertown Historic District - 3 min walk - 0.2 miles
  • Wilmer Park - 6 min walk - 0.4 miles
  • River Arts Chestertown - 6 min walk - 0.4 miles
  • Washington College - 8 min walk - 0.4 miles

Getting around

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

Restaurants

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

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.

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Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city center
  • 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
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
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. Onsite 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 each accommodation.

Frequently asked questions

How close is Circa 1900 Home in the Heart of Historic Downtown Chestertown to the airport?

This vacation home is 72.9 mi (104-min drive) away from the Baltimore, MD (MTN-Martin State) airport, the closest popular airport to the property.

Does Circa 1900 Home in the Heart of Historic Downtown Chestertown have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Circa 1900 Home in the Heart of Historic Downtown Chestertown to the beach?

This vacation home is 13 mi (21-min drive) from Betterton Beach and 13.8 mi (26-min drive) from Main Beach. Don't forget your sunscreen!

Does Circa 1900 Home in the Heart of Historic Downtown Chestertown offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

No, there is no casino at this vacation home.

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

Check-in begins at 3:00 PM.

Is there free parking at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

Free parking is not available at this vacation home.

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

This vacation home does not have a pool.

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

There are no spa services available at this vacation home.

How close is Circa 1900 Home in the Heart of Historic Downtown Chestertown to downtown Chestertown?

This vacation home is 0.7 mi away from Chestertown.

Reviews

Circa 1900 Home in the Heart of Historic Downtown Chestertown Reviews

10

Exceptional

10/10

Cleanliness
Rating 10 - Excellent. 76 out of 76 reviews
Rating 8 - Good. 0 out of 76 reviews
Rating 6 - Okay. 0 out of 76 reviews
Rating 4 - Poor. 0 out of 76 reviews
Rating 2 - Terrible. 0 out of 76 reviews

Reviews

10/10 Excellent

Darren H.

Liked: Cleanliness
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

10/10 Excellent

Maya L.

Liked: Cleanliness
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

10/10 Excellent

Michael H.

Liked: Cleanliness
Great Location and nice house!
Stayed 3 nights in Sep 2025

10/10 Excellent

Lora D.

Liked: Cleanliness
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

10/10 Excellent

Chris C., Richmond VA

Liked: Cleanliness

Great location, very comfy house

Lovely restored home on a very nice street in the heart of Chestertown. Comfy beds, loved the front porch. Cool coffee station! We had everything we needed, we really enjoyed our week's stay. Thank you to the owner for responding so promptly and resolving the problem with one of the shower faucets, really appreciated that.
Stayed 7 nights in Jun 2025

10/10 Excellent

Vijay S.

Liked: Cleanliness
Property was as described in the listing!! Very clean and well appointed with toiletries, towels, dishes, etc.Very clean, safe, quiet neighborhood.Enjoyed walking to the farmer's market, Evergrain Bread Company, and waterfront area.I would highly recommend if you're able to navigate the stairs!
Stayed 3 nights in May 2025

10/10 Excellent

Marcella M.

Liked: Cleanliness

Wonderful home in Chestertown

We rented four bedroom home in Chestertown for graduation weekend. Home has everything you could possibly need. All bedrooms are upstairs with one bathroom and one bathroom on lower level. If you have any elderly members of your party, this may be
Stayed 3 nights in May 2025

10/10 Excellent

Gary N.

Liked: Cleanliness
Great house, will stay again in the future.
Stayed 3 nights in Jun 2025

10/10 Excellent

Bethany M., Where do you live?

Liked: Cleanliness

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

10/10 Excellent

Nicole N.

Liked: Cleanliness

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

amy p.

Liked: Cleanliness

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

Sallie S.

Liked: Cleanliness

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

Downrigging Festival

We enjoyed everything about the property.
Stayed 4 nights in Oct 2024

10/10 Excellent

Darren H.

Liked: Cleanliness

Fall weekend

Lovely, well kept and tastefully furnished house in a great location.
Stayed 2 nights in Oct 2024

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