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Newly restored apartment in the heart of Chestertown

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A spacious living area with a dining table, sofa, and a kitchen in the background.
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.
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.

Reviews

10 out of 10
Exceptional

Entire apartment

2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Parking available

Explore the area

View in a map
Chestertown, MD
  • Place, Chestertown Historic District
    ‪1 min walk‬
  • Place, Historical Society of Kent County Maryland
    ‪2 min walk‬
  • Place, Washington College
    ‪9 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪126 min drive‬

Room options

About the neighborhood

Chestertown

This apartment places you next to Chestertown Historic District and Garfield Center for the Arts at the Prince Theater. The apartment includes a kitchen, a refrigerator, and a microwave.
View more Apartments in ChestertownOpens in a new window

What's nearby

  • Chestertown Historic District - 1 min walk - 0.1 miles
  • Historical Society of Kent County Maryland - 2 min walk - 0.1 miles
  • Wilmer Park - 3 min walk - 0.2 miles
  • River Arts Chestertown - 5 min walk - 0.3 miles
  • Washington College - 9 min walk - 0.5 miles

Getting around

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

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Dunkin - ‬2 min drive
  • ‪Royal Farms - ‬3 min drive
  • ‪Royal Farms - ‬5 min walk
  • ‪7-Eleven - ‬4 min walk

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.
The apartment is air-conditioned and features a kitchen and space to spread out with 2 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and a desk.

Similar properties

Exterior
Staybridge Suites Wilmington-Newark by IHG
Newark
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
8.2 out of 10, Very Good, 471 reviews
$114 nightly
The price is $126
Aug 30 - Aug 31
Total with taxes and fees
Staybridge Suites Wilmington-Newark by IHG

Property amenities

Internet

  • Available in the apartment: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • Games
  • Smart TV

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

Policies

Check-in

Check-in time starts at 4:00 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

Check-out instructions

The host requires you 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.

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 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
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: 4:00 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.

Frequently asked questions

What can I see close to this apartment?

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

How much does it cost to stay at Newly restored apartment in the heart of Chestertown?

As of Aug 28, 2026, prices found for a 1-night stay for 2 adults at Newly restored apartment in the heart of Chestertown on Sep 13, 2026 start from $385, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is there parking available at Newly restored apartment in the heart of Chestertown?

No, there isn't parking available at the apartment.

Is this apartment next to a casino?

No, this apartment is not connected to a casino.

Will I find an indoor pool at this apartment?

No, there is no indoor pool at this apartment.

What will couples enjoy most about a stay at Newly restored apartment in the heart of Chestertown?

Couples will appreciate amenities at this apartment, including a kitchen and a smart TV in each apartment and a kitchen in some.

Are there hot tubs at Newly restored apartment in the heart of Chestertown?

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

Does this apartment provide breakfast?

No, this apartment doesn't offer breakfast.

Will this apartment allow pets to stay free of charge?

No, pets aren't allowed at this apartment.

Are there connecting rooms at Newly restored apartment in the heart of Chestertown?

No, this apartment doesn't feature connecting guestrooms.

Where is the closest airport to this apartment?

The closest major airport to this apartment 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 27.4 mi away.

Are there rooms with balconies at Newly restored apartment in the heart of Chestertown?

No, there aren't any apartments at Newly restored apartment in the heart of Chestertown that offer a balcony.

Newly restored apartment in the heart of Chestertown Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 29 out of 32 reviews
Rating 8 - Good. 3 out of 32 reviews
Rating 6 - Okay. 0 out of 32 reviews
Rating 4 - Poor. 0 out of 32 reviews
Rating 2 - Terrible. 0 out of 32 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Verified traveler

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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
Verified review

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 review

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 review

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
Verified review

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 review

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
Verified review

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 review

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 review

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 review

10/10 Excellent

Dan B.

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

Very nice

Awesome
Stayed 4 nights in Aug 2024
Verified review

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
Verified review

10/10 Excellent

Michelle K.

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

Regatta getaway

This was a great apartment in an excellent location. We visited Washington college and attended a sailing regatta. The Evergrain Bakery across the street was amazing. Shops and restaurants all within walking distance! Apartment was well stocked, nicely decorated and clean! Also very close to the Hodson boathouse. It was a 3 minute drive!
Stayed 2 nights in May 2024