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Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Private Waterfront Estate | Pool, Dock, Kayaks

Wake up to water views, spend your day by swimming in the saltwater pool, kayaking in the river, or fishing on the dock, and end the evening with sunsets. This private 5-bedroom waterfront retreat is designed for families and groups looking to unwind, reconnect, and enjoy the best of Maryland’s Eastern Shore- equipped with high-speed internet- located 15 min from downtown Cambridge and 10 min from the Hyatt Regency Chesapeake Bay, the home is well positioned for wedding stays, and retreats.

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette, making your visit even more memorable! Just a 5 min drive from Blackwater Refuge! It's an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! The Tiny Cabin is located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

School Street Retreat: Cozy, artsy, central home

School Street is the perfect spot to launch adventures around Cambridge and the Eastern Shore. You get a full house with two bedrooms, two full bathrooms and beautiful native gardens. Just blocks from Great Marsh Point for boating, fishing, play and river access. Less than a mile to downtown historic Cambridge and the lighthouse/market. Quick drives to Easton, Vienna, Blackwater and more. Also provides great access to historic sites in the area. Come rest, relax and explore!

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.

The Cottage at Broad Creek

Your Private Waterfront Escape on Maryland's Eastern Shore Wake up to panoramic water views from your soaking tub. Kayak from the private dock, cook your catch in the chef's kitchen, then gather at your waterside fire pit and grill as the sun sets over the bay. Minutes from historic St. Michaels yet secluded enough to feel like your own sanctuary. Perfect for couples seeking both adventure and relaxation, whether celebrating a milestone or simply unplugging together.

Waterfront & Hot Tub! 4 BR/4 BA - Central Location

Enjoy this large peaceful Waterfront cabin-style home with your whole group! This beautifully updated home is super spacious, has lots of great amenities, and is centrally located for easy access to all that Cambridge has to offer! Huge backyard has an oversized patio with private hot tub, fire pit & beautiful water views! We are located on Hurst Creek off the Choptank River. Hurst Creek is a great calm waterway that can be enjoyed in kayaks or small power boats.

Tiny House on Maypop Homestead

Welcome to Maypop Homestead, our peaceful 14-acre retreat in historic San Domingo. Stay in a cozy tiny house surrounded by a lush forest and a wildlife-filled pond. Enjoy a queen bed, kitchenette, full bath with a composting toilet, meditation loft, Wi-Fi, and a large deck with a fire pit. We grow organic food, medicinal herbs, and flowers—tours and seasonal harvests available! Meet our friendly cats and relax in nature. Come enjoy a quiet, earthy escape.

Waterfront, Private Pier, Sleeps 10, 4 bedrooms

Escape to our waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure for everyone. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Waterfront Barn Loft with Modern Cabin Vibe

Relax in nature for a while in our beautiful and cozy barn loft. The loft is located next to our primary residence on 7 private acres along scenic Rewastico Creek, offering year round beauty. Kayak on, or relax by, the tidal marsh creek which is fed by the Nanticoke River and Chesapeake Bay. Centrally located between popular Eastern Shore destinations such as Atlantic beaches and historic small towns. A serene oasis with abundant wildlife.

Cottage on Cabin Creek

The cottage is the perfect getaway for couples. It is located on the water with two private piers for you to use. You may enjoy fishing, crabbing, kayaking, canoeing or bird watching from the piers. There is a charcoal grill available and a fire pit. The cottage is secluded enough for relaxation, but not far from local attractions and restaurants. Note the cottage is best suited for 1 to 2 people.