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Carriage House Hideaway in Middle of Chestertown

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Iron/ironing board, travel crib, free WiFi, bed sheets
Smart TV, fireplace
Fridge, microwave, oven, stovetop
Property grounds
Interior

Reviews

10 out of 10
Exceptional

Entire apartment

1 bathroomSleeps 2

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Fireplace
  • Air conditioning
  • Pet-friendly

Explore the area

Map
Chestertown, MD
  • River Arts Chestertown
    ‪6 min walk‬
  • Historical Society of Kent County Maryland
    ‪7 min walk‬
  • Washington College
    ‪8 min walk‬
  • Easton, MD (ESN-Easton - Newnam)
    ‪49 min drive‬

Room options

About the area

Chestertown

City center stay.Within a 10-minute walk of the apartment, you'll find Garfield Center for the Arts at the Prince Theater and River Arts Chestertown. Historical Society of Kent County Maryland and Washington College are also within half a mile (1 km).
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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

About this property

Entire place

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

Carriage House Hideaway in Middle of Chestertown

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

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Property grounds

Historic Downtown Garden Oasis with Private Patio

  • Kitchen
  • Free WiFi
  • Air conditioning
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5.0 out of 5, Exceptional, 29 reviews
Historic Downtown Garden Oasis with Private Patio

Property amenities

Internet

  • Available in the apartment: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • Bedsheets provided

Bathroom

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

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Fenced yard
  • Firepit
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city center
  • Near a hospital
  • Near the bay

Things to do

  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Rafting nearby
  • Sailing nearby
  • Swimming nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 25

Check-out

Check-out before 12:00 PM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 (weight limit: 50 lbs per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.
  • Note from host: No cribs are provided

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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

Property is also known as

Carriage House Hideaway in Middle of Chestertown Apartment
Carriage House Hideaway in Middle of Chestertown Chestertown

Carriage House Hideaway in Middle of Chestertown Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 83 out of 87 reviews
Rating 8 - Good. 4 out of 87 reviews
Rating 6 - Okay. 0 out of 87 reviews
Rating 4 - Poor. 0 out of 87 reviews
Rating 2 - Terrible. 0 out of 87 reviews

10/10

Cleanliness

10/10

Amenities

9.8/10

Property conditions & facilities

Reviews

10/10 Excellent

Jessica V.

Liked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

Great stay!

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

8/10 Good

Verified traveller

Liked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

Comfortable gem

Two great days in Chestertown
Stayed 2 nights in Apr 2024

10/10 Excellent

Cathleen K.

Liked: Cleanliness

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.

Liked: Cleanliness

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

Liked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

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.

Liked: Cleanliness

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

Liked: Cleanliness, property conditions & facilities
Stayed 1 night in Oct 2023

10/10 Excellent

anthony, Dewey Beach

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

10/10 Excellent

Cailin H.

Liked: Cleanliness

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.

Liked: Cleanliness

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

Liked: Cleanliness

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

10/10 Excellent

Catherine

Liked: Cleanliness, property conditions & facilities
Stayed 2 nights in Sep 2023