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Newly restored apartment in the heart of Chestertown

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Fridge, microwave, oven, stovetop
Living area
Exterior
2 bedrooms, desk, free WiFi, bed sheets
Living area

Reviews

9.8 out of 10
Exceptional

Entire apartment

2 bedrooms1 bathroomSleeps 4

Popular amenities

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

Explore the area

View in a map
Chestertown, MD
  • Historical Society of Kent County Maryland
    ‪2 min walk‬
  • River Arts Chestertown
    ‪5 min walk‬
  • Washington College
    ‪12 min walk‬
  • Easton, MD (ESN-Easton - Newnam)
    ‪57 min drive‬

Room options

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Property grounds

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  • Free WiFi
  • Air conditioning
  • Outdoor space
5.0 out of 5, Exceptional, 39 reviews
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About this property

Entire place

You'll have the entire apartment to yourself and will only share it with other guests in your party.

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.
During your stay at this apartment building, you're just a quick walk from Chestertown Historic District. You'll find features like laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the apartment.
  • Air-conditioned apartment with kitchen, washing machine, and living room
  • Free WiFi
  • Amenities include laundry facilities
  • Steps from Chestertown Historic District and Garfield Center for the Arts at the Prince Theater
This apartment offers its guests laundry facilities. The front desk is open around the clock.

This Chestertown apartment is smoke free.

Property amenities

Internet

  • Available in the apartment: Free WiFi

Parking and transport

  • Parking on site

Kitchen

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

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

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: 18

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

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

  • 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

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
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

Newly restored apartment in the heart of Chestertown Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 23 out of 26 reviews
Rating 8 - Good. 3 out of 26 reviews
Rating 6 - Okay. 0 out of 26 reviews
Rating 4 - Poor. 0 out of 26 reviews
Rating 2 - Terrible. 0 out of 26 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Maggie D.

Liked: Cleanliness

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

10/10 Excellent

Douglas G.

Liked: Cleanliness

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

10/10 Excellent

Eliza M.

Liked: Cleanliness

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

10/10 Excellent

Jeffrey W.

Liked: Cleanliness

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

10/10 Excellent

Karen G., Gettysburg, PA

Liked: Cleanliness

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

10/10 Excellent

April D.

Liked: Cleanliness

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

8/10 Good

Russell C.

Liked: Cleanliness

Great location

Nice downtown location.
Stayed 2 nights in Feb 2025

10/10 Excellent

Jacquelin N. W.

Liked: Cleanliness

Perfect

Stayed 4 nights in Oct 2024

10/10 Excellent

Katherine P.

Liked: Cleanliness

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

10/10 Excellent

Dan B.

Liked: Cleanliness

Very nice

Awesome
Stayed 4 nights in Aug 2024

10/10 Excellent

Sarah

Stayed 3 nights in Jun 2024

10/10 Excellent

Michelle K.

Liked: Cleanliness

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

10/10 Excellent

Tamara H.

Liked: Cleanliness

Lovely Home

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

8/10 Good

Carlos C.

Liked: Cleanliness

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

10/10 Excellent

Gary C.

Liked: Cleanliness

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

10/10 Excellent

Linda Carol K.

Liked: Cleanliness

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

10/10 Excellent

Alison W.

Liked: Cleanliness

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

10/10 Excellent

Verified traveller

Liked: Cleanliness

Great stay

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

10/10 Excellent

Mark C.

Liked: Cleanliness

Great Stay

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

10/10 Excellent

Betsy G.

Liked: Cleanliness

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

10/10 Excellent

Deborah K.

Liked: Cleanliness

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

8/10 Good

Kathy and Rick R.

Liked: Cleanliness

Great place

Very clean
Stayed 2 nights in May 2023

10/10 Excellent

Erin D.

Liked: Cleanliness

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

10/10 Excellent

Michael. T.

Liked: Cleanliness

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

10/10 Excellent

terry c.

Liked: Cleanliness

Julie was great. Attentive and quick to respond. Very clean, well equipped apartment.

Terrific. with the exception of the church clock chime..no fault of Julie.
Stayed 3 nights in Mar 2023