Historic Downtown Garden Oasis with Private Patio

Entire guest suite in Chestertown, Maryland

  1. 2 guests
  2. 1 bedroom
  3. 1 bed
  4. 1 bath
Hosted by Stephen
  1. Superhost
  2. 3 years hosting

Listing highlights

Top 1% of homes

This home is one of the highest ranked based on ratings, reviews, and reliability.

Self check-in

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Walkable area

Guests say this area is easy to get around.
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!

The space
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, 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.

Guest access
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.

Other things to note
We're committed to providing our guests with a 5-star 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!

Where you’ll sleep

What this place offers

Garden view
Kitchen
Fast wifi – 319 Mbps
Dedicated workspace
Free driveway parking on premises – 1 space

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Rated 4.97 out of 5 from 87 reviews.

Guest favorite
This home is in the top 1% of eligible listings based on ratings, reviews, and reliability
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Overall rating

  1. 5 stars, 97% of reviews
  2. 4 stars, 3% of reviews
  3. 3 stars, 0% of reviews
  4. 2 stars, 0% of reviews
  5. 1 stars, 0% of reviews

Rated 5.0 out of 5 stars for cleanliness

Rated 5.0 out of 5 stars for accuracy

Rated 5.0 out of 5 stars for check-in

Rated 5.0 out of 5 stars for communication

Rated 5.0 out of 5 stars for location

Rated 4.9 out of 5 stars for value

Where you’ll be

Chestertown, Maryland, United States
This listing's location is verified and the exact location will be provided after booking.

Neighborhood highlights

Welcome to Chestertown, Maryland – a charming and historic town nestled along the banks of the Chester River. With its quaint streets lined with beautiful colonial architecture and stunning waterfront views, Chestertown is the perfect destination for those seeking a peaceful and picturesque getaway.

In Chestertown, there's something for everyone. Founded in 1706, history buffs can explore the town's rich heritage through its many historic sites and museums, while nature lovers can enjoy the scenic beauty of the Chester River and nearby parks and wildlife preserves. Foodies will delight in the town's vibrant culinary scene, which features everything from traditional Maryland crab cakes to farm-to-table cuisine made with locally sourced ingredients.

But perhaps the best thing about Chestertown is its sense of community. Whether you're strolling through the town's farmer's market, attending one of its many festivals and events, or simply chatting with the friendly locals, you'll feel right at home in this welcoming and vibrant town.

Meet your hosts

Born in the 70s
Speaks English
My partner, Marianna, and I are former Brooklynites now living the good life in Chestertown, MD. We love to travel, especially to Italy, and enjoy the way vacation rentals give you a more authentic feel of a city or place. We hope to host you or be hosted by you in the near future.
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Stephen is a Superhost

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Response rate: 100%
They typically respond within an hour
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Things to know

House rules

Check-in after 3:00 PM
Checkout before 11:00 AM
2 guests maximum

Safety & property

Exterior security cameras on property
Carbon monoxide alarm
Smoke alarm

Cancellation policy