See all properties
Apartment

Carriage House Hideaway in Middle of Chestertown

Family-friendly apartment in 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
1 bathroomSleeps 2

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a map
Chestertown, MD
  • Place, River Arts Chestertown
    ‪5 min walk‬
  • Place, Washington College
    ‪8 min walk‬
  • Place, Wilmer Park
    ‪9 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪106 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.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Outdoor dining
Historic Downtown Garden Oasis with Private Patio
  • Kitchen
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space
10.0 out of 10, Exceptional, (45 reviews)
Historic Downtown Garden Oasis with Private Patio

House Rules

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

Children

Children allowed: ages 0–17
No cribs are provided
default

Events

No events allowed
default

Pets

Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
default

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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Chestertown

Located in Chestertown, this apartment is in the city centre. 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 Crumpton Auction and Hazel Miner Monument. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Apartments in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • River Arts Chestertown - 5 min walk - 0.4 km
  • Historical Society of Kent County Maryland - 8 min walk - 0.7 km
  • Washington College - 8 min walk - 0.7 km
  • Chestertown Historic District - 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
  • ‪Royal Farms - ‬5 min walk
  • ‪Dunkin - ‬2 min drive
  • ‪Royal Farms - ‬4 min drive
  • ‪McDonald'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 23 kg 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 24 Jan, 2026, prices found for a 1-night stay for 2 adults at Carriage House Hideaway in Middle of Chestertown on 25 Jan, 2026 start from S$292.34, 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 at Carriage House Hideaway in Middle of Chestertown?

On-site 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?

Checkout is at 12:00 PM.

Where is Carriage House Hideaway in Middle of Chestertown located?

Located in the centre 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 labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 98 out of 102 reviews
Rating 8 - Good. 4 out of 102 reviews
Rating 6 - Okay. 0 out of 102 reviews
Rating 4 - Poor. 0 out of 102 reviews
Rating 2 - Terrible. 0 out of 102 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

10/10 Excellent

Mary T.

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

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

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

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

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

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

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

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

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

10/10 Excellent

anthony

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

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

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

10/10 Excellent

Christina

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

10/10 Excellent

Robert S., Nashville, TN

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

10/10 Excellent

Robert S., Nashville, TN

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

Wonderful stay

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

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

10/10 Excellent

eugene c.

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

Downtown Graden

Lovely stay.
Stayed 2 nights in May 2023

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

10/10 Excellent

Paul R.

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

Another Wonderful Stay in Chestertown

We love the Carriage house. It is just perfect- from arrival to departure. The incredible hosts have thought of everything for guests and we so appreciate it! Grounds are gorgeous and accommodations- so comfortable yet strikingly beautiful- from the super comfy bed and surroundings to the art filled walls. Could not have been a better stay,! Arlo agrees!
Stayed 2 nights in Apr 2025

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

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

10/10 Excellent

Karen G., Gettysburg, PA

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

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

10/10 Excellent

Linda T.

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

Perfection!

Second stay here this year. It’s becoming our eastern shore home away from home.
Stayed 4 nights in Aug 2023

10/10 Excellent

Janet C.

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

Adorable studio

Very sweet studio with everything you need for your stay. Extremely quiet and walking distance to great restaurants and shops. Hosts were very gracious and available if needed. We definitely will book again. Thank you!
Stayed 3 nights in Jan 2025

About the host

Hosted by Robert Kestell

Host profile image

Languages:

Spanish, Portuguese
Tell us how we can improve our siteShare feedback