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Circa 1900 Home in the Heart of Historic Downtown Chestertown

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4 bedrooms, desk, iron/ironing board, free WiFi - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)
TV, books - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)
Fridge, microwave, oven, stovetop - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)
TV, books - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)
Interior - Circa 1900 Home in the Heart of Historic Downtown Chestertown (Chestertown)
On a picturesque one-way street lined with historic homes, this 1900-built house combines old-world charm with modern comforts. Stroll to the Chester River Waterfront, Saturday farmers market, and Chestertown Marina or enjoy free on-street parking outside your doorstep.

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

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 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

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

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

Located in Chestertown, this holiday home is in the city centre. Historical Society of Kent County Maryland and Betterton Historic District are local landmarks, and some of the area's activities can be experienced at Rolphs Wharf Marina and Cassinelli Winery and Vineyards. Take the opportunity to explore the area for water adventures such as fishing and other activities like birdwatching. Visit our Chestertown travel guide
View more Holiday homes in Chestertown
Map
Chestertown, MD

What's nearby

  • Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.
    Washington College
    8 min walk - 0.7 km
  • Historical Society of Kent County Maryland
    2 min walk - 0.2 km
  • Garfield Center for the Arts at the Prince Theater
    3 min walk - 0.3 km
  • Wilmer Park
    6 min walk - 0.6 km
  • River Arts Chestertown
    6 min walk - 0.6 km

Getting around

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

Restaurants

  • Milano's Pizzeria
    4 min drive
  • Royal Farms
    4 min drive
  • Dunkin
    2 min drive
  • McDonald's
    4 min drive
  • Royal Farms
    3 min walk

Frequently asked questions

Is Circa 1900 Home in the Heart of Historic Downtown Chestertown pet-friendly?

No, pets are not allowed at this property.

How much is parking at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

On-site parking is available at the 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

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 79 out of 79 reviews
Rating 8 - Good. 0 out of 79 reviews
Rating 6 - Okay. 0 out of 79 reviews
Rating 4 - Poor. 0 out of 79 reviews
Rating 2 - Terrible. 0 out of 79 reviews

10

Cleanliness

10

Location

Reviews

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

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

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

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

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

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

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

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

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

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

Diane P.

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

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

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

Marcella M.

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

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

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

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

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

10/10 Excellent

Michael H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Location and nice house!
Stayed 3 nights in Sep 2025

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

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

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

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

Chris C.

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

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

David F.

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

Downrigging Festival

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