Entire home

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Vacation home in Chestertown with kitchen and patio

Choose dates to view prices

Where to?

Dates

October 2025

November 2025

4 bedrooms, desk, iron/ironing board, free WiFi

Overview
Amenities
Policies
Location

Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 6

Popular amenities

Dryer
Washer
Kitchen
Parking available
Barbecue grill
Air conditioning

Explore the area

Chestertown, MD

Place, Historical Society of Kent County Maryland
‪2 min walk‬
Place, River Arts Chestertown
‪6 min walk‬
Place, Washington College
‪11 min walk‬
Airport, Easton, MD (ESN-Easton - Newnam)
‪57 min drive‬

Room options

About the neighborhood

Chestertown

This vacation home places you next to Historical Society of Kent County Maryland and Chestertown Historic District. The vacation home includes a kitchen, a patio, and a fenced private yard.

View more Vacation Homes in Chestertown

What's nearby

Historical Society of Kent County Maryland - 2 min walk - 0.1 miles
Wilmer Park - 6 min walk - 0.4 miles
River Arts Chestertown - 6 min walk - 0.4 miles
Washington College - 11 min walk - 0.6 miles
Rolphs Wharf Marina - 12 min drive - 5.6 miles

Getting around

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

Restaurants

‪McDonald's - ‬4 min drive
‪Royal Farms - ‬3 min walk
‪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.

The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a patio, and there's space to spread out with 4 bedrooms. Guests can enjoy a TV and stay connected with free WiFi. Other standard amenities include a washing machine, a fenced private yard, and a coffee maker.

Similar properties

Kitchen
Washer
Dryer
Free WiFi

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

Pets

This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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

Check-in: 3:00 PM
Check-out: 11:00 AM
Minimum check-in age: 21

We should mention

Details about charges, deposits, or other important information:

This property is managed by a private host, not a professional engaged in trade or business.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Onsite parties or group events are strictly prohibited.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.

Frequently asked questions

What's there to see close to this vacation home?

This vacation home is located in Chestertown, just steps from Historical Society of Kent County Maryland and Chestertown Historic District, and within a short walk of Wilmer Park. You'll also find Garfield Center for the Arts at the Prince Theater and Kings Town Park less than a mile away.

Is parking available on site at this vacation home?

No, this vacation home doesn't offer parking.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What do couples enjoy most about Circa 1900 Home in the Heart of Historic Downtown Chestertown?

At this historic vacation home, amenities that appeal to couples include a kitchen, kitchens in some accommodations, as well as a garden.

Are there hot tubs at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

No, there isn't a spa tub at this vacation home.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay free of charge?

No, pets aren't allowed at this vacation home.

Does this vacation home have connecting rooms?

No, there aren't connecting rooms at this vacation home.

How close is the airport from this vacation home?

The closest major airport to this vacation home is Baltimore, MD (MTN-Martin State), which is about 20.8 mi away. Another top airport is Easton, MD (ESN-Easton - Newnam), which is around 27.5 mi away.

Are there rooms with balconies at Circa 1900 Home in the Heart of Historic Downtown Chestertown?

Yes, every accommodation at Circa 1900 Home in the Heart of Historic Downtown Chestertown comes with a deck.

Circa 1900 Home in the Heart of Historic Downtown Chestertown Reviews

Exceptional

10/10

Cleanliness

10/10 Excellent

Michael H.

Sep 24, 2025

Liked: Cleanliness

Great Location and nice house!

Stayed 3 nights in Sep 2025

10/10 Excellent

Lora D.

Aug 15, 2025

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

Jul 6, 2025

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.

Jun 13, 2025

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.

Jun 10, 2025

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.

Jun 8, 2025

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?

Apr 6, 2025

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.

Mar 20, 2025

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.

Jan 24, 2025

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.

Dec 19, 2024

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.

Nov 5, 2024

Liked: Cleanliness

Downrigging Festival

We enjoyed everything about the property.

Stayed 4 nights in Oct 2024

10/10 Excellent

Darren H.

Oct 31, 2024

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.

Sep 8, 2024

Liked: Cleanliness

Stayed 4 nights in Aug 2024

10/10 Excellent

Mary D.

Aug 25, 2024

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

Jul 7, 2024

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

May 12, 2024

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.

Dec 29, 2023

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.

Dec 6, 2023

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.

Nov 6, 2023

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.

Oct 2, 2023

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

Sep 18, 2023

Liked: Cleanliness

Perfect

Great house, location and host!

Stayed 3 nights in Sep 2023

10/10 Excellent

Tricia L., Washington, DC, USA

Aug 8, 2023

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.

Jul 31, 2023

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.

Jul 22, 2023

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.

Jul 14, 2023

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