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Cozy Guest House Near Park

This lovely guest house is located in the historic district of Cambridge within 3 blocks to the Great Marsh/Gerry Boyle waterfront park. This cozy space includes a full kitchen with dishes, living space with reclining sofa, new Bedstory medium firm bed separated by an antique armoire as well as a large bathroom. You will have a private parking area and separate entryway through a private courtyard. Less than 1 mile to historic Cambridge. Near the start of annual races and waterfront activities.

Little Slice of Cambridge. 2 bedroom, pet friendly

You’ll be staying right in the center of the Historic district, close enough to walk to town and enjoy shopping or some of the great restaurants. Just two blocks from the water, a short stroll to the lighthouse or down to the water front and enjoy the park. This newly listed 2 bedroom , pet- friendly apartment has everything you will need to explore the history, food and waterfowl found in this area. Park your boat here. We can’t wait for you to experience Cambridge and relax in the “West End”.

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Away at the Bay: New Home on the Chesapeake Bay!

Welcome to Away at the Bay! A new build, 4 bedroom house right on the Chesapeake Bay. Very family friendly, and in walking distance to a small community beach. Enjoy kayaking, biking, and crabbing on Kent Island right out of your front door. Perfect for multiple families (especially with younger kids) or attending one of the many wedding venues! 15 minutes off the Bay Bridge and easy access to groceries stores, outlet shopping, and restaurants. Come stay with us and enjoy being away at the bay!

Loon Cottage on Leeds Creek

Loon Cottage is a place where you can get away, put your phones down, take long walks in the woods, read on the patio, canoe on the river, cook big meals, and spend time with your favorite people. It’s cozy, comfortable, and just a little bit nostalgic. Decamp from the City to work remotely for a few days. Bring the family out to change the scenery on your weekend routine. Pack friends into the car for some low key shenanigans. Or some combination of all the above. Follow along @loon_cottage

25-50% Off~Private Beach~Hot Tub~Fire Table~

Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers. Escape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.

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.

Shipwrights Cottage in Town!

Charming historic cottage within walking distance to all St. Michaels has to offer! Relax & enjoy the sights of town from your front porch! Once a working shipwrights cottage, this home is 2 stories with a 1st floor full kitchen, combo living-dining room, den with queensize pullout couch & full bath. The 2nd floor has 2 bedrooms & a full bath. Both bedrooms have vaulted ceilings & ceiling fans. The primary bedroom has a private sitting balcony. Walk to shops, restaurants & waterfront!

Charming House, Quiet Neighborhood (Entire House)

This beautiful house has it all: the charm of a 1960s brick ranch with a fully updated interior. All new flooring, new appliances, and new furniture create a fresh, clean feel. The Chesapeake Bay is in view across the street and the full acre backyard offers a quiet, peaceful view of nature. The outdoor dining table and love seat provide the perfect setting for a peaceful visit. This property is 5 minutes from downtown Easton, 15 minutes from St. Michael's. License #STN 22-23.

Relax on Kent Island in 4 Bedroom Home w/Waterview

Enjoy your vacation in this Beautiful & Stylish 4 Bedroom Home with a view of the Chesapeake Bay! Perfect for Families & Wedding Groups. We are conveniently located to many areas/cities: Annapolis- 20 miles Baltimore- 45 Wash. DC- 50 Easton- 35 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions. This is a Non-Smoking House. Also No Pets or Parties & 11 max guests (8 max adults). Book Today!

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.

Stunning Chesapeake waterfront home

Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. Enjoy Town Creek and Tred Avon water views from every room and angle. Gorgeous sunsets from the wraparound porch, stargazing and fishing from the dock. Walk to Morris Street for a relaxed coffee, stroll through Town Park, or take the Ferry to St. Michaels. The Town of Oxford has issued short term rental license # STR25-06 for this property.