Historic Downtown Garden Oasis with Private Patio | Apartment in Chestertown

10.0 (35 Reviews) |   1 Bedroom  1 Bathroom  2 Guests
Chestertown Apartment | Historic Downtown Garden Oasis with Private Patio

1 Bedroom Apartment in Chestertown

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesthouse is the perfect place for couples or solo travelers to enjoy a long relaxing weekend. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer. We look forward to hosting you!
Our guesthouse is a two-floor 525 sqft unit with a queen bedroom and en suite bathroom upstairs, and a living room with dining/working area and kitchenette downstairs. You'll love the private patio space, which offers separate seating and dining areas with beautiful views of our garden and access to the fully-fenced backyard and grill.
We are proud to give back to our town through the renting of our guesthouse. Five percent of our gross revenue is donated to one or more local non-profits annually. Additionally, the guesthouse features artwork from local artists and galleries, and you'll find home goods and products from nearby shops.
Our place is designed to provide you with everything you need for a comfortable stay, including fast wifi, a private entrance with self check-in via keyless entry, and free street or off-street parking.
You'll find all the essentials like towels, bed sheets, soap, and toilet paper, as well as a hairdryer, cleaning products, shampoo, conditioner, and body soap. There are extra pillows and blankets, and hangers to store your clothes.
The guesthouse has two brand new air conditioning and heating units that you control, so you will be comfortable year-round. Safety is a top priority, so we have a smoke and carbon monoxide alarm, a fire extinguisher, and a first aid kit on hand.
In the kitchenette, you'll find a microwave, dishes, silverware, cups, a mini-fridge with freezer, a hot water kettle, a coffee maker (both a Keurig and a Nespresso), wine glasses, and a toaster.
During your stay you will have exclusive access to the following rooms and spaces:
- Bedroom
- Full bathroom
- Kitchenette
- Living room
- Dining area
- Patio
Additionally, you'll be sharing the backyard with us, but we'll do our best to give you privacy during your stay.
If you have any questions or concerns about the areas you can access, or if you need any additional information about your stay, please don't hesitate to ask.
We're committed to providing our guests with an exceptional experience, and we're always available to answer any questions or provide recommendations to help make your stay unforgettable.
Here's what some of our recent guests have said about their stay:
"Perfect apartment-type accommodation located in a lovely walkable town. These hosts literally thought of a guest's every need... Besides being a comfortable, beautiful space top to bottom with an abundance of windows, the things that really stood out for us are: Self-check in keyless entry, gallery artwork throughout; large stone-top table with chairs for eating, gathering, working, etc; coffee machine with Keurig AND Nespresso pods (WOW!)" - Cindy
"Their place was exactly what I was looking for! It was clean, cute, centrally located, but yet private and offered everything I needed for my stay! I loved the special touches from the local businesses, the espressos, coffee, and tea options. Their place was spotless and the bed was extremely comfortable! They were also very responsive with any questions I had. If I ever come back to the area I will definitely stay at their place." - Megan
"Great place and location. Private and quiet, but walkable to restaurants of Chestertown. Comfortable and super clean! Very cute, indoors and out." - Joan
"Stephen and Marianna were delightful hosts for a perfect getaway weekend in Chestertown! Their detailed suggestions of local restaurants and events made our stay more enjoyable, as were their thoughtful messages to us during our stay to ensure that everything was going well. The apartment is such a gem tucked away in a courtyard at the back of their house in the historical section of town!" - Carla
We're confident that you'll love your stay at our guesthouse, and we can't wait to welcome you.
Book now to secure your spot!

Historic Downtown Garden Oasis with Private Patio is located in Chestertown. Historic Downtown Garden Oasis with Private Patio provides accommodation, featuring Kitchen, Air Conditioner, Parking, among other amenities. This Apartment features Kitchen, Air Conditioner, Parking, to make your stay a comfortable one.

Historic Downtown Garden Oasis with Private Patio 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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Chestertown, 21620, United States

Amenities

Air Conditioner
Parking
Balcony/Terrace
Security/Safety
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Shower
  • Hair dryer
  • Towels provided
  • Soap
  • 1 bathroom
  • Toilet paper
  • Shampoo
Bedroom
  • Bed sheets provided
  • 1 bedroom
  • Dining table
  • Living room
  • Dining room
Kitchen
  • Freezer
  • Microwave
  • Spices
  • Cookware/dishes/utensils
  • Toaster
  • Coffee/tea maker
  • Refrigerator (mini)
  • Paper towels
  • Electric kettle
Laundry
  • Near laundromat
Parking
  • Free offsite parking
  • Onsite parking
  • Onsite parking includes off-street options
Pet Friendly
  • No pets allowed
Accessibility
  • Smoke-free property
Activities
  • Ecotours nearby
  • Fishing nearby
  • Golf nearby
  • Cycling nearby
  • Kayaking nearby
  • Power boating nearby
  • Fitness facilities nearby
  • Winery tours nearby
  • Sailing nearby
Entertainment
  • Books
  • Stereo
General
  • Unit size: 517 sq ft (48 sq m)
  • Local artist showcase
  • English
  • Near a hospital
  • In the city center
  • In a rural location
Internet
  • Free WiFi
Outdoors
  • Patio
  • Fenced yard
  • Garden
  • Outdoor furniture
  • Barbecue grill
Security/Safety
  • First aid kit
  • Fire extinguisher
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Deadbolt lock

Policies

Check-in
Check-in time starts at 3:00 pm minimum check-in age: 25
Check-out
Check-out before 11:00 am
Child Policy
Children are welcome. note from host: while not child friendly, we can accommodate.
Event Policy
No events allowed
Pet Policy
Pets not allowed
Smoking Policy
Smoking is not permitted
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

Reviews

Tammy S.
Apr 14, 2025 10:06:21 PM
Review Score:   10
Summary: We loved staying at Stephen and Marianna’s fantastic home. The space is bright and well-decorated, it’s private and had all of the amenities we needed. The location is wonderful and we were able to walk a couple of blocks to the stores and restaurants and enjoyed the Saturday morning farmers market. When we checked in, the keypad wasn’t working but within about a minute, Stephen appeared and let us in so it was all very easy and nice. Highly recommend staying here - perfect for a couple to do a weekend getaway!
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FAQ's

Is this Chestertown apartment pet-friendly for guests?

No, pets are not 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 $199 per night with includes Wellness Facilities, Fireplace/Heating, Child Friendly, Balcony/Terrace, Bedding/Linens, Entertainment, Barbecue/Outdoor Cooking, Internet, Kitchen, Air Conditioner, Parking, Security/Safety with all other facilities. RBO matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

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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