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House On The Hill - Historic Private Second Floor

This Guest Space is the full second floor. Have the second floor to yourself, w/private bathroom, sitting area, and two bedrooms. NOTE: host live on the first floor. The family cat Andy might pay a visit (friendly). You use the front door and go right up the steps to your space. The shared part is you can see our space on the stairs and thus may here us but we are quiet. Walking distance to town! Hang out outside & enjoy chairs and a fire-pit if you wish, or take the 5 min walk downtown.

Hygge Haven: A cozy apartment in a canal-side town

Chesapeake City is a historic town located on the C & D Canal; it's not unusual to be greeted by locals as you explore the town. The apartment is a bedroom with sitting area, fully equipped kitchen & bath. It's in the heart of the town & walkable to all the boutiques, restaurants & nightlife! It comes equipped with a Nespresso machine, coffee pods,sparkling water, wifi & tv if you just want to chill. It's steps from the canal for lovely sunrise/sunsets! There are bike/walking paths nearby.

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

BNB Breeze Presents Harbor View Haven This exquisite waterfront property offers a captivating retreat to relax and recharge with stunning views and an array of desirable features! With a serene waterfront location, this idyllic home provides a picturesque setting for unplugging and experiencing outdoor enjoyment. Your extensive amenity list includes: 💦 Hot Tub 🔥 Outdoor Gas Fireplace ☕️ Jura Espresso Machine 🚤 Private Dock + Kayaks 🚴 Bikes for Exploring 🏓 Ping-Pong Table 🌅 Bay Views

Waterfront historic district 1BR Apartment

Take it easy at this unique and peaceful riverfront getaway. Third floor, one bedroom apartment with its own private rooftop deck and beautiful views of the Chester River. Located at the end of a street on the water, but still in the historic district offering convenience and privacy. A short stroll to everything Chestertown has to offer. Off street parking. Kayaks or canoe available with notice or bring your own. Enjoy coffee and sunrise from deck or Adirondacks. NO CLEANING FEE!

Waterfront Log Cabin with Hot Tub

Situated on the water's edge of Muddy Creek, this newly renovated log cabin offers a unique, luxury getaway for those seeking a stay immersed in all that nature has to offer. While relaxing on the spacious outdoor deck, you will be treated with a panoramic view of Muddy Creek complete with an occasional sighting of the neighborhood eagle. Perfectly set up for a romantic getaway for two, The Log Cabin on Muddy Creek was created to provide a space for couples to rest and reconnect.

Cabin on the Creek ~ Kayaks and Fire Pit

Unwind in our cabin tucked away on a private lane mins from Chestertown. We are situated on 6.5 wooded acres, perched up on 100’ bluff overlooking Churn Creek, a tributary off the Chesapeake Bay. Idyllic water views framed by a canopy of oak trees. Enjoy nature as you relax outside by the fire pit or stroll down to the ‘point’ to take in wildlife, or take a kayak out to explore the creek and water fowl. Deer come up through the woods and are often spotted on the property.

Long Beach Cottage, Hot Tub, Beachfront

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

Quarry Landing • River Views in Historic Town

Enjoy easy access to everything from this perfectly located home. Quarry Landing is a turn-of-the-century Duplex filled with charm and beauty. Located on High Street in the quaint small town of Historic Port Deposit, (Maryland), perfect for couples or families. Great location in a safe neighborhood, short walk to local eateries, waterfront promenade, playground, fishing pier, dog park, and much more.

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

Wigwam Lodge is an experience nestled in a pine & hard wood forest with rural privacy. Incredibly spacious decks. Surround Forest Views inside and out! 5-min from Choptank river, 20-min from Historic Denton, Irish Pub & Grocery, 1hr from the beach. Easy PARKING 10ft from the front door. Solid WIFI! Click “Show More” Below to SEE ALL Deets...