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Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Private Guesthouse | 7-acres | Near wedding venues

Welcome to The Warehouse! This private guesthouse nestled on Kent Island's Warehouse Creek is thoughtfully decorated, offering rustic charm and unmatched privacy—just minutes from the Bay Bridge. Whether you're attending a wedding, planning a romantic escape, or enjoying a family getaway, this cozy retreat is a perfect, fully stocked alternative to a hotel stay. Enjoy the spacious yard, water views, serene surroundings, and easy access to Kent Island venues, Annapolis, DC, and the Eastern Shore.

Cheerful & Spacious Shore Life Beauty!

Welcome to our charming yet peaceful abode & island oasis where sailing, marine life, & bay exploration exceed the standard! This exceptional home is conveniently located to a variety of high quality restaurants, parks, outdoor activities, spas, beaches, wedding venues, & other entertainment including live music, hunting, & antiquing while also being 20-minutes from Annapolis & 1-hour from Baltimore City & DC. Let this be your definitive choice for a magical destination you'll forever remember.

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

Waterfront Getaway w/ Pool + Beaches+ Hot Tub +BBQ

Unwind at this serene and secluded getaway—perfect for couples, small groups, families or anyone looking to relax by the water. This charming one-bedroom guest house offers comfort and style with a plush king-size bed, a fully equipped kitchen with a gas stove, and a spacious living area with a queen-size pullout sofa. Step outside to your private, oversized balcony overlooking the river—an ideal spot for morning coffee, al fresco dining, or winding down with sunset views and a glass of wine.

Comfortable Single Floor Living

Make some memories at this unique and family-friendly place. Comfortable one floor living with space to spread out, hang out, and enjoy! Split design with master on one end opposite other sleeping . Inside bar area and covered deck to kick back and relax. Fenced area for your four-legged friends, and a sport court out back for a casual game of basketball or pickleball. Everything you should need inside to feel at home. Sights and sounds give you that country feel without being too remote.

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

Waterfront Modern Guest Barn

Find peace and reconnect with nature at this award winning guest barn. With its simple geometry and bucolic setting overlooking a quiet river of the Eastern Shore, this gem at the edge of a farm field could easily be mistaken for a working barn. But when you slide open the pair of two-story barn doors, you find a beautiful modern guesthouse full of light from the wall of windows facing the river. The setting is incredibly peaceful, and is a wonderful romantic escape or family getaway.

Captain’s Quarters - Unique home on Corsica River!

The Captains Quarters was built in 1880 by local waterman, Captain John H. Osman. The Captain built 4 identical houses for the Captains of his fleet to enjoy. The Captains Quarters is registered with the Maryland National Historical Trust. This unique and cozy home takes you back in time, all while enjoying all of the modern amenities. Our guests can expect to enjoy coffee on the patio overlooking the Corsica River, games and a bar in the brick floor basement and tons of relaxation!

Quaint Waterfront- access, Private Shorehouse-unit

Location is everything in this comfy and affordable private unit located on the Chester River and Winchester Creek with water views. Also enjoy the hosts private water front amenities such as fishing at our private pier, boating, kayaking, paddle boarding or simply relax at the waterfront for morning coffee and sunrises or enjoy the fire pit in the evening. The community playground and beach are just steps away. Close proximity to restaurants, shopping, trails, and wedding venues.

Bay Breeze - 3BR Waterfront Chester River Retreat

Remodeled in 2023, this light-filled, 2-story private home offers 2,100 sqft of stylish comfort—perfect for a relaxing getaway. Take in breathtaking sunsets from the double-decker porches overlooking the Chester River, unwind by the fire pit, host a crab feast or enjoy a BBQ on the private dock. Ideally located just 5-10 minutes from Kent Island’s top restaurants and wedding venues, with a community playground, pavilion, and boat ramp just steps away. Your waterfont escape awaits!

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.