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Newly restored apartment in the heart of Chestertown

Photo gallery for Newly restored apartment in the heart of Chestertown

A spacious living area with a dining table, sofa, and a kitchen in the background.
A compact laundry room with two front-loading washing machines, a white cabinet above, and a wooden shelf.
A modern kitchen with white cabinets, a central island, and pendant lighting.
A bedroom with a large bed, a nightstand, a lamp, a patterned rug, and a view through an open door to a hallway.
A modern kitchen with a large island, white cabinetry, and a view of the city.

Reviews

10 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • At the centre of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Walk to Washington College
Sleeps 4•2 bedrooms•2 beds

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Free Wi-Fi
  • Dryer

Explore the area

View in a map
Chestertown, MD
  • Place, Chestertown Historic District
    ‪1 min walk‬
  • Place, Garfield Center for the Arts at the Prince Theater
    ‪2 min walk‬
  • Place, Washington College
    ‪9 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪126 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Kitchen

About this property

Newly restored apartment in the heart of Chestertown

Newly renovated apartment in downtown Chestertown. Directly across the street from Evergrain Bakery. In the center of all Chestertown has to offer. This apartment span the entire front of a recently restored building, built in 1877. Open living room/dining area/kitchen Historic character with all modem conveniences, including dishwasher, washer/dryer, TV with AppleTv and high speed wifi internet access. Off street parking for one car on first come first served basis with ample street parking.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Remove personal items and remove leftover food and drinks
Turn off the lights, lock the doors and return the keys
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Property # 3217085vb
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

About the area

Chestertown

Chestertown is home to this apartment. Historical Society of Kent County Maryland and Betterton Historic District are local landmarks, and the area's natural beauty can be seen at Chesapeake Bay and Chestertown Historic District. Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center are also worth visiting.
View more Apartments in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Chestertown Historic District - 1 min walk - 0.1 km
  • Historical Society of Kent County Maryland - 2 min walk - 0.2 km
  • Garfield Center for the Arts at the Prince Theater - 2 min walk - 0.2 km
  • Wilmer Park - 3 min walk - 0.3 km
  • Washington College - 9 min walk - 0.8 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 105 min drive

Restaurants

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

Frequently asked questions

Is Newly restored apartment in the heart of Chestertown pet-friendly?

No, pets are not allowed at this property.

How much is parking at Newly restored apartment in the heart of Chestertown?

On-site parking is available at the property.

What time is check-in at Newly restored apartment in the heart of Chestertown?

Check-in begins at 4:00 PM.

What time is check-out at Newly restored apartment in the heart of Chestertown?

Checkout is at 11:00 AM.

Where is Newly restored apartment in the heart of Chestertown located?

Situated in Chestertown, this apartment building is steps away from Chestertown Historic District, Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. Sumner Hall and Wilmer Park are also within 5 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 28 out of 31 reviews
Rating 8 - Good. 3 out of 31 reviews
Rating 6 - Okay. 0 out of 31 reviews
Rating 4 - Poor. 0 out of 31 reviews
Rating 2 - Terrible. 0 out of 31 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Susan A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!
Stayed 7 nights in Jul 2026
Verified

10/10 Excellent

Verified traveller

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

Great stay

Wonderful spot in the center of historical Chestertown,
Stayed 2 nights in Sep 2023
Verified

8/10 Good

Russell C.

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

Great location

Nice downtown location.
Stayed 2 nights in Feb 2025
Verified

10/10 Excellent

Mark C.

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

Great Stay

The unit was really nice and location was perfect.
Stayed 2 nights in Aug 2023
Verified

10/10 Excellent

Maggie D.

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

Perfect Stay in a Great Location

Extremely clean, beautifully updated, and very comfortable. Perfect location—easy to walk to shops and restaurants. Would absolutely stay again!"
Stayed 3 nights in Jul 2025
Verified

10/10 Excellent

Betsy G.

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

Great place

The place was clean, well organized and decorated and a fantastic location. Would definitely go back again.!
Stayed 1 night in Jul 2023
Verified

10/10 Excellent

Carla D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely apartment in a very convenient location downtown. It had everything we needed.
Stayed 3 nights in Sep 2025
Verified

8/10 Good

Carlos C.

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

Good Location - Nice and Clean

Located in the center of town, with easy access to Restaurants and the River. Easy to get in and out and parking available.
Stayed 2 nights in Mar 2024
Verified

10/10 Excellent

Karen G.

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

Excellent location right downtown!

Great place / very spacious/ bed super comfy - kitchen has everything you need. Easy entry instructions - best location right downtown - near everything and an easy walk up to the college. Looking forward to staying here again!
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

Tamara H.

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

Lovely Home

The location was great. The decor was pretty and all very comfortable
Stayed 3 nights in Apr 2024
Verified

10/10 Excellent

Deborah K.

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

Fabulous renovated apartment in prime location

we loved the location and being able to walk to the shops and restaurants in Chestertown.
Stayed 2 nights in Jun 2023
Verified

10/10 Excellent

Jeffrey W.

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

Great stay in Chestertown

We had a great experience and stay in Chestertown. We stayed during Easter weekend so we could visit out son at Washington College. The apartment is in a great location. Our host was fantastic and very helpful. We will definitely be booking again next year.
Stayed 2 nights in Apr 2025
Verified

8/10 Good

Kathy and Rick R.

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

Great place

Very clean
Stayed 2 nights in May 2023
Verified

10/10 Excellent

April D.

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

Sparkling clean and great location

We loved this apartment. The communication with the owner was very timely and clear!
Stayed 2 nights in Mar 2025
Verified

10/10 Excellent

Michael. T.

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

Excellent Location and Great Property!

We stayed in this great apartment and found it to be in excellent condition and in a great location. Walking distance to all the shops, restaurants and bars Chestertown has to offer. The host was great to work with and we will be staying here again on our next trip to Chestertown!
Stayed 2 nights in Mar 2023
Response from VrboOwner on 30 May 2023
Michael, I look forward to having you back. In the last couple of months there have been some great additions to Chestertown, including a Float Spa, ice cream store and a new jewelry store on the ground level of the building. Julie
Verified

10/10 Excellent

Eliza M.

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

Far better than a hotel

Booked this for a wedding since there were limited hotel options in town and everyone was jealous of our setup! Everything was spotless and the place is adorable. Worked out perfectly and you are walking distance from everything in town. Highly recommend!
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Douglas G.

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

Memorial Weekend

We stayed here for Memorial weekend and the location was perfect for watching the Tea Party Parade! The property is directly across the street from Evergrain which is perfect for coffee and baked goods. Shopping was within walking distance which was so convenient. Beds were very comfortable and the place was really clean. We will definitely stay here again!
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Erin D.

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

Washington College Sr. Weekend

Best location to be in walking distance that all Chestertown has to offer. Property was clean and had all we needed and more.
Stayed 2 nights in Apr 2023
Response from VrboOwner on 30 May 2023
I am glad you enjoyed your stay. If you come back you will find more additions to town, including a new jewelry store on the ground level.
Verified

10/10 Excellent

Jaclyn B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay. Very Clean unit. Perfect for a quick few days in Chestertown in the heart of the downtown. Only thing Was just a little difficult to figure out what unit was ours and there are stairs everytime you have to go to the unit so just for those who may need assistance with stairs this wouldn’t be ideal. Overall great space! Thanks Julie we will be back!
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Gary C.

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

Chesapeake Getaway

This property, located in downtown Chestertown, provided a relaxing getaway for my wife and I to explore the quaint towns of the Chesapeake Bay region. We were able to explore the area, including a walk through Annapolis, starting and ending our day with Chestertown coffee and pastry shops, restaurants, and taverns.
Stayed 2 nights in Feb 2024
Verified

10/10 Excellent

Tara M.

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

Amazing Apartment

I would stay there anytime. Apartment is clean and spacious. Convenient to center of town. Owner was easy and amazing to work with. 5 stars.
Stayed 2 nights in Feb 2023
Response from VrboOwner on 30 May 2023
Thank you for staying with us and hope to see you again!
Verified

10/10 Excellent

Katherine P.

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

Perfecton

We fell in love with Chestertown and are so glad we stayed in the heart of downtown at this charming vrbo. Everything was perfect. Will return and recommend
Stayed 2 nights in Oct 2024
Verified

10/10 Excellent

Linda Carol K.

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

Convenient to everything.

The location could not be better. I could walk anywhere in town. The space is large. The host was very easy to communicate with both before and during the stay.
Stayed 3 nights in Dec 2023
Verified

10/10 Excellent

Dan B.

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

Very nice

Awesome
Stayed 4 nights in Aug 2024
Verified

10/10 Excellent

Alison W.

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

Perfect

We came to Chestertown for a wedding and fell in love with this town and apartment. The apartment is perfectly located across from a bakery and next door to an incredible restaurant, the Kitchen. The apartment is so clean and perfectly comfortable for a family of 4.
Stayed 2 nights in Sep 2023

About the host

Hosted by Julie Santoboni

Host profile image

Languages:

English, German, Italian

Premier Host

They consistently provide great experiences for their guests
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