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Carriage House Hideaway in Middle of Chestertown

Family-friendly stay with in-room kitchens in Chestertown

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Photo gallery for Carriage House Hideaway in Middle of Chestertown

Smart TV, fireplace
Exterior
Iron/ironing board, travel crib, free WiFi, bed sheets
Dining
Shower, hair dryer, towels, soap

Reviews

10 out of 10
Exceptional

Entire apartment

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, Washington College
    ‪8 min walk‬
  • Place, Wilmer Park
    ‪9 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪106 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. Chestertown Historic District and Historical Society of Kent County Maryland are also within half a mile (1 km).
View more Apartments in ChestertownOpens in a new window

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

  • ‪Royal Farms - ‬5 min walk
  • ‪Dunkin - ‬2 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Procolino's - ‬3 min drive
  • ‪7-Eleven - ‬6 min walk

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 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.

Similar properties

Property grounds
First Floor Studio Apartment in Historic Chestertown
  • Pool
  • Hot tub
  • Washer
  • Dryer
4.8 out of 5, Exceptional, 108 reviews
The price is CA $138
CA $221 total
includes taxes & fees
Jan 20 - Jan 21
First Floor Studio Apartment in Historic Chestertown

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
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shampoo
  • 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

  • Smoking not allowed

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
Information provided by the property may be translated using automated translation tools

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

Events

No events allowed

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
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. 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

Reviews

10/10 Excellent

Janet Y.

Liked: Cleanliness
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

Mary T.

Liked: Cleanliness
Lovely place, perfectly appointed.
Stayed 1 night in Dec 2025

10/10 Excellent

Jessica K.

Liked: Cleanliness
Stayed 2 nights in Oct 2025

10/10 Excellent

jay b.

Liked: Cleanliness
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

Cindy K.

Liked: Cleanliness
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

Mary Ann B.

Liked: Cleanliness
Our experience was very delightful. The apartment was attractive, pleasant and very comfortable.
Stayed 1 night in Oct 2025

10/10 Excellent

Jennifer M.

Liked: Cleanliness
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

Jennifer D.

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

10/10 Excellent

Colleen A.

Liked: Cleanliness
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

Deborah D.

Liked: Cleanliness
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

maria r., Ocean City MD

Liked: Cleanliness
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

JoLynne R.

Liked: Cleanliness

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

10/10 Excellent

Barbara D.

Liked: Cleanliness

A perfect retreat

This well appointed and well maintained carriage house was more than we could ask for and the location was perfect. The bedding and linens were high end, there were an excess of shampoos and toiletries, even laundry detergent for the downstairs laundry. Beth and Bob were the perfect hosts, friendly, easily accessible and made great suggestions. The property was beautiful, the gardens lush and welcoming. We were an easy 2 block walk to restaurants and shops. Altogether, a very pleasant stay.
Stayed 2 nights in Jun 2025

10/10 Excellent

Vickie K.

Liked: Cleanliness

Wonderful Place to stay

Our stay was Sat 5/10-Mon 5/12 This is a tremendous value, conveniently situated within walking distance of shops and restaurants in the heart of downtown. Beth and Bob were exceptional hosts, demonstrating great hospitality and very accommodating. The accommodations were precisely as depicted in the photographs. The quaint charm of the secluded, beautiful setting was truly captivating. Chestertown holds a special place in our hearts as our hometown, and it was a pleasure to return for a visit. The town’s beauty is undeniable, and we wholeheartedly recommend extending our stay here in the future.
Stayed 2 nights in May 2025

10/10 Excellent

Paul R.

Liked: Cleanliness

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.

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