Apartment in Chestertown, MD
2 guests · 1 bedroom · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this apartment rental
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. Additionally, for awareness, there is a Ring Video Doorbell installed on the front door of the primary house. It is used to monitor our front door but not the door of the guest unit.
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!
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. Additionally, for awareness, there is a Ring Video Doorbell installed on the front door of the primary house. It is used to monitor our front door but not the door of the guest unit.
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!
Amenities at Historic Downtown Garden Oasis with Private Patio
Non-smoking
No pets allowed
Map of Chestertown, MD
Ratings and reviews
10 / 10Outstanding·Feb 2026
Wonderful location and amenities! Hosts were helpful and informative
10 / 10Outstanding·Dec 2025
Everything was perfect and cozy. Stephen and Marianna are wonderful hosts and have anticipated all of our needs yet again. Their rental is inviting and beautifully appointed.
10 / 10Outstanding·Nov 2025
Only wonderful things to say about this sweet apartment. First, the hosts, Stephen and Mariana, are incredibly hospitable and full of great ideas and recommendations for the area. This property is very clean and roomy (for two), has wonderful amenities and the hosts have thought of everything that makes this our go to place to stay when we are in Chestertown. This property is in a historic area, an easy walk to the river, the historic district, shops, a nature center, park, and many restaurants. It is an easy drive to anywhere requiring a car and parking is available and convenient. We highly recommend!
10 / 10Outstanding·Oct 2025
Perfect quaint property! everything you would need provided except we didn’t realize there was no TV but that was us not the property. Highly recommend. great location. walk to everything Chestertown.
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Top rated by guests
10Outstanding
(54 Ratings)
"Wonderful location and amenities! Hosts were helpful and informative "
Henry Z.Don't miss out! Price and availability may change
