Chestertown Apartments

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- PatioAdditionally, 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!" - CarlaWe'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!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.While not child friendly, we can accommodate..About customRules:There is a maximum stay of one month for Instant Bookings. For longer stays, please message the host first. Otherwise, your booking may be cancelled..The max number of guests is two people. If you are two adults traveling with a child under 5, we can accommodate but you must let us know at booking..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Newly renovated apartment in downtown Chestertown. Directly across the street from Evergrain Bakery. In the center of all Chestertown has to offer. This apartment span the entire front of a recently restored building, built in 1877. Open living room/dining area/kitchen Historic character with all modem conveniences, including dishwasher, washer/dryer, TV with AppleTv and high speed wifi internet access. Off street parking for one car on first come first served basis with ample street parking.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

• Embrace historic charm in our exquisitely renovated third-floor walk-up, located in a beautiful historic building in the Chestertown Historic District.• Perfectly positioned to overlook Fountain Park and within walking distance of Washington College and all of downtown Chestertown.• Enjoy unique furnishings that blend early 1900s decor with modern comforts.• Indulge in luxury amenities with priority booking access at Park Row Floats, a renowned exclusive Float Spa located just below the space. Pippin’s Retreat offers:• Two bedrooms, each featuring a queen bed.• Two full bathrooms, with the primary bedroom offering an ensuite.• A large, fully-equipped modern kitchen with a view of Fountain Park.• A comfortable living room with characteristic furnishings, opening onto a sizeable back deck - perfect for relaxing or entertaining.• We use Melaleuca's nontoxic, plant-based cleaning products to ensure a healthy, chemical-free environment for your stay.Guest access• You will have the entire third floor to yourself, including the large back deck that provides an elevated view across the historic rooftops of Chestertown.• Access through the rear exterior staircase or enjoy walking up the original historic stairway inside the main front lobby, with its charmingly narrow design reflective of the early era.Other things to note• We cherish the building's historic elements and ask guests to be mindful of the unique charm of the narrow staircase.• Visit the Park Row Floats website to make a Spa appointment.• We use Melaleuca's nontoxic, plant-based cleaning products to ensure a healthy, chemical-free environment for your stay. These eco-friendly cleaners leave your space fresh and welcoming, perfect for guests with sensitivities or anyone looking to avoid harsh chemicals. Relax knowing your comfort and the planet are prioritized - ideal for Washington College parents cheering on their students!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.