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Carriage House Hideaway in Middle of Chestertown

Photo gallery for Carriage House Hideaway in Middle of Chestertown

Living area
Interior
Room
Interior
Room

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
1 bathroomSleeps 2

Popular amenities

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

Explore the area

View in a map
Chestertown, MD
  • Place, River Arts Chestertown
    ‪5 min walk‬
  • Place, Garfield Center for the Arts at the Prince Theater
    ‪6 min walk‬
  • Place, Washington College
    ‪8 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪126 min drive‬

Rooms & beds

0 bedrooms (sleeps 2)

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Kitchen
Outdoor play area
Garden

About this property

Carriage House Hideaway in Middle of Chestertown

Escape to a secluded, romantic second story studio apartment in the middle of Chestertown. Private parking, and over an acre of gardens to call your own. Totally private with views of nature all around, this is the perfect place to relax in front of the fireplace. (Electric, but very cozy and realistic.)
Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and coffee maker.
Comfortable king bed, kitchenette, and washer dryer. Filtration system for pure delicious drinking water.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet friendly
Free WiFi
Air conditioning

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 12:00 PM
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Children

Children allowed: ages 0-17
No cribs are provided
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Events

No events allowed
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Pets

Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total)
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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, a first aid kit, and a deadbolt lock

About the neighborhood

Chestertown

Located in Chestertown, this apartment is in the city center. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center. Traveling with kids? Consider Crumpton Auction and The Mainstay. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking/biking trails and cycling.
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Map
Chestertown, MD

What's nearby

  • River Arts Chestertown - 5 min walk - 0.4 km
  • Garfield Center for the Arts at the Prince Theater - 6 min walk - 0.6 km
  • Historical Society of Kent County Maryland - 8 min walk - 0.7 km
  • Washington College - 8 min walk - 0.7 km
  • Wilmer Park - 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
  • ‪Royal Farms - ‬4 min drive
  • ‪Procolino's - ‬3 min drive

Frequently asked questions

Is Carriage House Hideaway in Middle of Chestertown pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 50 lbs per pet. Some restrictions may apply, so please contact the property for more details.

How much does it cost to stay at Carriage House Hideaway in Middle of Chestertown?

As of Apr 25, 2026, prices found for a 1-night stay for 2 adults at Carriage House Hideaway in Middle of Chestertown on May 26, 2026 start from $195, 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.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Carriage House Hideaway in Middle of Chestertown?

Check-in begins at 3:00 PM.

What time is check-out at Carriage House Hideaway in Middle of Chestertown?

Check-out is at 12:00 PM.

Where is Carriage House Hideaway in Middle of Chestertown located?

Located in the center of Chestertown, this family-friendly apartment building is within a 10-minute walk of Garfield Center for the Arts at the Prince Theater, Chestertown Historic District, and Wilmer Park. Historical Society of Kent County Maryland and Sumner Hall are also within 10 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 100 out of 104 reviews
Rating 8 - Good. 4 out of 104 reviews
Rating 6 - Okay. 0 out of 104 reviews
Rating 4 - Poor. 0 out of 104 reviews
Rating 2 - Terrible. 0 out of 104 reviews

10/10

Cleanliness

10/10

Amenities

9.8/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

charlie e.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great little getaway. Enjoyed our time in Chestertown very much.
Stayed 1 night in Apr 2026
Verified

10/10 Excellent

Mary T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely place, perfectly appointed.
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

Janet Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely stay. The carriage house was clean, cozy and well furnished. Beth and Bob were very welcoming. Perfect!
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Beverly A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The only thing to change would be the ability to access streaming. What was available was limited. Otherwise the place was great
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

jay b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. Very clean. Can get in earlier than most and have plenty of morning left to go more places before leaving. Would definitely book again.
Stayed 1 night in Oct 2025
Verified

10/10 Excellent

Mary Ann B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our experience was very delightful. The apartment was attractive, pleasant and very comfortable.
Stayed 1 night in Oct 2025
Verified

10/10 Excellent

Jennifer D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Super clean. Charming, well-appointed rental in a great location.
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Zara D.

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

Great stay!

Everything was as described — great location, communication and property!
Stayed 3 nights in Sep 2024
Verified

10/10 Excellent

anthony

Liked: Cleanliness, property conditions & facilities, communication
great location and really nice property
Stayed 1 night in Oct 2023
Verified

10/10 Excellent

Cindy K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This lovely carriage house was spotlessly clean and beautifully decorated. It was walking distance from all downtown restaurants and historic buildings. The owners were very responsive. Just perfect!
Stayed 1 night in Oct 2025
Verified

10/10 Excellent

Jennifer M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The carriage house was great! It is walkable to both town and Washington College activities. It is quiet and secluded. The garden is lovely! It is an oasis in the middle of town!
Stayed 1 night in Oct 2025
Verified

10/10 Excellent

Christina

Liked: Cleanliness, amenities, property conditions & facilities, communication
Fantastic location, gorgeous space, and great host!
Stayed 3 nights in May 2023
Verified

10/10 Excellent

Robert S.

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

Great stay

Wonderful place for my wife and I visiting our son at Washington College
Stayed 2 nights in Aug 2023
Verified

10/10 Excellent

Colleen A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was great. The grounds were beautiful, and the living space open and relaxing. A very charming place, quiet, relaxing and enjoyable. Feels likes I found a hiden treature.
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

Robert S.

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

Wonderful stay

Lovely carriage house room for the weekend
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Susan K.

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

Nice Stay

A cute studio that had everything, plus walking distance to historic and shopping areas. I would stay there again!
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

JoLynne R.

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

Beautiful private space

This is a great place to stay! It’s very private and quiet. The room is perfect, with plenty of extra space and very well stocked bathroom and small kitchen area. There is a beautiful yard with chairs to relax. It was a short walk to the downtown area for shopping, dinner or drinks. I highly recommend this place.
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

maria r.

Liked: Cleanliness, check-in, communication, location, listing accuracy
After dozens of stays through VRBO, this is the first one that my husband walked into and said, "This place is gorgeous!". The house had everything we needed, the bed was very comfortable, and the grounds were stunning. The hosts were generous, and we truly enjoyed our stay.Thanks so much for sharing your house with us.
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

eugene c.

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

Downtown Graden

Lovely stay.
Stayed 2 nights in May 2023
Verified

10/10 Excellent

Deborah D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property is exactly as pictured. It is well furnished and appointed. The location is perfect: walking distance to town. The kitchen is supplied with several appliances . WiFi access is great. I plan to stay here again, with my pup. The gardens are beautiful and having access to them is a bonus.
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

Randall

Liked: Cleanliness, amenities, property conditions & facilities, communication
We love this property. Friendly owners, great amenities, walking distance to you downtown. We would stay here again in a heartbeat.
Stayed 3 nights in Jun 2023
Verified

10/10 Excellent

Marianne

Liked: Cleanliness, amenities, property conditions & facilities, communication
We enjoyed our stay at the carriage house. Was a perfect location to walk to town, was super clean and very nicely decorated. The hosts were very nice and made us feel welcomed. I would definitely stay here again and would recommend to others.
Stayed 1 night in Sep 2022
Verified

10/10 Excellent

Karen G.

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

Great Location / Nice and Cozy

Loved this little gem in town! We only stayed one night but it has everything you need. Very spacious / bed was comfy / walk into town or to the college. We’ll stay here again for sure !
Stayed 1 night in Apr 2023
Verified

10/10 Excellent

Jen L.

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

Charming spot

The property had everything we needed. The garden was lovely and in its full springtime beauty. Would definitely stay again.
Stayed 2 nights in Apr 2023
Verified

10/10 Excellent

Kathleen E.

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

Lovely Carriage House

Such a cozy little place with everything we needed. The bed was great, the kitchen well stocked and the electric fireplace was an added bonus. Easy walk into town
Stayed 2 nights in Oct 2024

About the host

Hosted by Robert Kestell

Host profile image

Languages:

Spanish, Portuguese
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