Carriage House Hideaway in Middle of Chestertown

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Apartment

Overview
Amenities
Policies
Location
Host

Exceptional

1 bathroomSleeps 2

Popular amenities

Dryer
Washer
Fireplace
Air conditioning
Pet-friendly

Explore the area

Chestertown, MD

River Arts Chestertown
‪6 min walk‬
Historical Society of Kent County Maryland
‪7 min walk‬
Washington College
‪8 min walk‬
Aberdeen, MD (APG-Phillips Army Airfield)
‪91 min drive‬

Rooms & beds

0 bedrooms (sleeps 2)

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Kitchen

Outdoor play area

Garden

About this property

Escape to a secluded, romantic studio getaway 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 queen bed, kitchenette, and washer dryer.

Property manager

Robert Kestell

Languages

Portuguese, Spanish

Add dates for prices

Amenities

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

Air conditioning

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Kitchen
Free WiFi
Air conditioning
Outdoor space

House Rules

Check in after 3:00 PM

Minimum age to rent: 25

Check out before 12:00 PM

Children

Children allowed: ages 0–17

No cribs are provided

Events

No events allowed

Pets

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

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.

Chestertown, MD

What's nearby

Garfield Center for the Arts at the Prince Theater - 6 min walk - 0.5 km
River Arts Chestertown - 6 min walk - 0.6 km
Historical Society of Kent County Maryland - 7 min walk - 0.6 km
Washington College - 8 min walk - 0.7 km
Rolphs Wharf Marina - 11 min drive - 7.9 km

Getting around

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

Restaurants

‪McDonald's - ‬3 min drive
‪Dining Hall - ‬12 min walk
‪Procolino Pizza - ‬3 min drive
‪China House - ‬3 min drive
‪The Freeze - ‬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.

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, Wilmer Park and Historical Society of Kent County Maryland. River Arts Chestertown and Washington College are also within 10 minutes.

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Amenities

9.8/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

10/10 Excellent

Paul R.

21 Apr, 2025

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

Jessica V.

31 Mar, 2025

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

AMAZING!

If I could give these hosts 10 stars, I would! They went above and beyond for me! Their kindness and helpfulness was way beyond what I would have expected from a host. The carriage house is adorable! It is comfy, clean and quiet. It is stocked with a coffee maker, a toaster, an air fryer, a microwave, etc. If you need it, it probably there!I just cannot say enough about these hosts and their adorable carriage house rental.

Stayed 2 nights in Mar 2025

10/10 Excellent

Janet C.

23 Jan, 2025

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

10/10 Excellent

Kathy H.

8 Dec, 2024

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

Excellent and very cozy place to stay!!! 5 Star ++++

the Carriage House Hideaway in Chestertown, MD was absolutely perfect, and one of the best places we have ever stayed. It is a delightful and welcoming upper floor location that was very centrally situated (walking distance) to all the shops/restaurants/historical locations in Chestertown. Very clean, plenty of room, and just like the pictures conveyed. Very cozy and welcoming atmosphere, with everything you need for a stay. The property owners made us feel very welcome and were readily available if we needed anything (which we did not, as all was perfect to start). I would highly recommend the Carriage House and will look forward to visiting them in the future. Thank you!!

Stayed 2 nights in Dec 2024

10/10 Excellent

Stephen C.

11 Nov, 2024

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

Another wonderful stay!

The carriage house is beautifully furnished, and very clean. The location excellent. It's a five minute walk to everything downtown Chestertown has to offer. This was my second stay with Bob and Beth. They are wonderful hosts. Looking forward to my next visit!

Stayed 4 nights in Nov 2024

10/10 Excellent

Christopher B.

7 Nov, 2024

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

Sultana Weekend

Great place. Very spacious for two people and very cozy with electric fireplace and easy chairs. Well equipped kitchenette. About a three minute walk to the center of town and 15 minutes to marina. We are likely to stay there again

Stayed 3 nights in Oct 2024

10/10 Excellent

Kathleen E.

14 Oct, 2024

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

Kelly B.

7 Oct, 2024

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

Lovely Studio Near Town

What a lovely studio near town! The location was unbeatable for my friend's wedding in Chestertown where all the events took place on High Street. The area is quiet and serene. The studio came equipped with everything you could ask for and more. I will stay here again when visiting Chestertown.

Stayed 2 nights in Sep 2024

10/10 Excellent

Zara D.

30 Sept, 2024

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

8/10 Good

Verified traveller

22 Sept, 2024

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

Great lil’ spot to enjoy Chestertown.

Stayed two nights in town for a wedding. Perfect spot to rest our head at night and so close to town to enjoy the market and shops. Clean room, great linen, kind hosts. More comfortable than a hotel for sure. Delightful small find in our searc!

Stayed 2 nights in Sep 2024

10/10 Excellent

amy r.

19 Sept, 2024

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

super fabulous

we had the most delightful weekend in chestertown as guests at the carriage house. the space was super well-appointed, from the comfy and plush bed to the kitchen with all the necessary items to be comfortable and not really have to leave. the property feels like a beautiful secret garden, but is so very close to the center of chestertown. we will be back. :)

Stayed 3 nights in Sep 2024

10/10 Excellent

William W.

21 Aug, 2024

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

Excellent stay

Beautiful home in quiet neighborhood. Homes was in excellent condition. The host answer my call when I had a question. I recommend them to everyone.

Stayed 3 nights in Aug 2024

10/10 Excellent

Julie D.

1 May, 2024

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

Perfect spot

Bob and Beth's apartment was absolutely perfect for us. It was the cleanest VRBO that we have ever stayed in. All of the amenities were above and beyond what we expected. The apartment is in a great location and walkable into town and the WC campus. We will definitely stay again when we come back to town.

Stayed 2 nights in Apr 2024

10/10 Excellent

Paul R.

21 Apr, 2024

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

Comfortable gem

Two great days in Chestertown

Stayed 2 nights in Apr 2024

10/10 Excellent

Cathleen K.

9 Apr, 2024

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

Chestertown Charm

Absolutely love staying here for the charm of a private, spacious studio in a great location. Easily walk to town but yet quiet. Unit was clean and very comfortable!

Stayed 1 night in Apr 2024

10/10 Excellent

Jan J.

1 Jan, 2024

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

Highly recommend!

Our stay at Beth and Bob’s carriage house was delightful. The location is perfect. The parking is convenient. The accommodations are perfect. Very comfortable for two. The hosts were very gracious. They allowed us to check in early and offered that we could stay beyond the checkout time. Also, the process for locating the carriage house and parking, and finalizing at the end was very easy and well explained. We love Chestertown and Beth & Bob’s place, so we’ll be back for sure!

Stayed 2 nights in Dec 2023

10/10 Excellent

Brooke H., Bethesda, MD

10 Dec, 2023

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

Cute, clean, cozy, pet friendly

The property was clean and comfortable. It was a very short walk to town and I appreciated the reserved off street parking spot right behind the carriage house. The owners were very responsive and friendly. I would definitely stay again!

Stayed 2 nights in Dec 2023

10/10 Excellent

Mary Beth K.

15 Nov, 2023

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

Cozy Owl Cottage

Perfect. Lively grounds, close proximity to town and a beautiful comfortable place to unwind.

Stayed 4 nights in Nov 2023

10/10 Excellent

robert B.

30 Oct, 2023

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

Weekend in Chestertown

Nice efficiency apartment above a garage. Easy access and walkable to restaurants and shops.

Stayed 2 nights in Oct 2023

10/10 Excellent

Val S.

27 Oct, 2023

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

Wonderful Stay

I adore this charming carriage house. It's a tranquil slice of paradise tucked away on a quiet dead end street, yet just a short stroll, a block and a half away, from all the vibrant shops and restaurants in Chestertown. You can reach the waterfront in just a leisurely 10-minute walk. We found everything we required readily available, and Beth was incredibly supportive, promptly addressing any questions we had. Our aspiration is for the Owl Tree Carriage House to become our cherished retreat during our stays in Chestertown.

Stayed 1 night in Oct 2023

10/10 Excellent

Patricia

23 Oct, 2023

Liked: Cleanliness, property conditions & facilities, communication

Stayed 1 night in Oct 2023

10/10 Excellent

anthony

15 Oct, 2023

Liked: Cleanliness, property conditions & facilities, communication

great location and really nice property

Stayed 1 night in Oct 2023

10/10 Excellent

Cailin H.

9 Oct, 2023

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

Excellent stay!

We had a wonderful stay here! We were in town from NYC for a friend’s wedding and we are happy we picked this spot. The place was spacious, very open and fit the two of us well. It was perfectly located an easy walk to town. It was rainy all weekend so we didn’t get to explore the grounds, but they looked lovely! The kitchen was very well stocked. The hosts were informative, kind and easy to communicate with. We will recommend this place to our many family and friends in the DC area looking for a weekend out of the city and we hope to come back! Wouldn’t hesitate to book again!

Stayed 2 nights in Sep 2023

10/10 Excellent

doreen f.

1 Oct, 2023

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

Birthday/College visit

We truly appreciated all the tips and assistance that our host provided! Great location- able to walk into town, along the river and to WAC. It is a perfect and private carriage house with all the extra available!!

Stayed 1 night in Sep 2023

10/10 Excellent

Karen G., Gettysburg, PA

21 Sept, 2023

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

Perfect Location

Great stay in downtown Chestertown! I've stayed several times now and will be back again another time. Walk everywhere in town and the kitchen has every gadget you'll need. Great communication / easy access / and comfy!

Stayed 1 night in Sep 2023