Chestertown Rentals USA Maryland Chestertown

Carriage House Hideaway in Middle of Chestertown | Apartment in Chestertown

10.0 (92 Reviews) |   Pet Friendly   1 Bedroom  1 Bathroom  2 Guests  Stay&Play
Chestertown Apartment | Carriage House Hideaway in Middle of Chestertown

1 Bedroom Apartment in 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.

Carriage House Hideaway in Middle of Chestertown is located in Chestertown. Carriage House Hideaway in Middle of Chestertown provides accommodation, featuring Security/Safety, Fireplace/Heating, Entertainment, among other amenities. This Apartment features Security/Safety, Fireplace/Heating, Entertainment, to make your stay a comfortable one.

Carriage House Hideaway in Middle of Chestertown has 1 Bedroom , 1 Bathroom, and max occupancy of 2 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Apartment because of the excellent services rendered by the owner or manager of this Apartment, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Apartment has a friendly neighborhood, and the Chestertown has interesting places to visit. If you want to learn more about the Apartment in Chestertown, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • TV
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Check-in Check-in time starts at 3:00 pm minimum check-in age: 25
Check-out Check-out before 12:00 pm
Child Policy Children are welcome. note from host: no cribs are provided
Pet Policy 2 total (up to 50 lbs per pet) pets allowed restrictions apply; for more information contact the property at the number on the booking confirmation service animals are welcome, and are exempt from fees welcoming dogs only
Other Policy 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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
 
Chestertown, 21620, United States

What Our Guests say 500 + Reviews

Apr 1, 2025 05:45:29 AM
Summary: 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.
Jessica V. Jessica V.
Jan 24, 2025 04:20:49 AM
Summary: 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!
Janet C. Janet C.
Dec 9, 2024 07:18:19 AM
Summary: 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!!
Kathy H. Kathy H.
Nov 11, 2024 10:58:25 AM
Summary: 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!
Stephen C. Stephen C.
Nov 7, 2024 09:59:23 AM
Summary: 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
Christopher B. Christopher B.
Oct 15, 2024 12:57:01 AM
Summary: 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
Kathleen E. Kathleen E.
Oct 7, 2024 08:31:21 PM
Summary: 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.
Kelly B. Kelly B.
Oct 1, 2024 12:19:56 AM
Summary: Everything was as described — great location, communication and property!
Zara D. Zara D.
Sep 23, 2024 05:36:49 AM
Summary: 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!
Sep 20, 2024 06:34:24 AM
Summary: 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. :)
amy r. amy r.

FAQ's

Is this Chestertown apartment pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Chestertown apartment have a swimming pool?

No, this Chestertown apartment does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Chestertown apartment?

Best-rates for the Chestertown apartment starts from $166 per night with includes Security/Safety, Fireplace/Heating, Entertainment, Air Conditioner, Parking, Pet Friendly, TV, Balcony/Terrace, Wellness Facilities, Child Friendly, Internet, Sports/Activities, Bedding/Linens, Barbecue/Outdoor Cooking, Kitchen, Laundry StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Chestertown apartment a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this apartment Good or guests have recommended them suitable for families. As reported by the owner or manager, the apartment has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Chestertown apartment wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Chestertown apartment has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Chestertown apartment?

Based on the information reported by the owner or manager, the Chestertown apartment indicates 1 day stay policy at this apartment. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Chestertown apartment?

Based on the information reported by the owner or manager, details for the cancellation policy for the Chestertown apartment are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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