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Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5 Star retreat for those who value tranquility over spectacle. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

Bayview Bungalow - Water view, EV charging station

One level living with a view across the Chesapeake Bay of the most amazing sunsets over the Annapolis skyline. Enjoy the large fully stocked kitchen, spacious bedrooms, claw foot tub & separate shower, deck, bbq grill, fire pit, & yard. Take the bikes on the local trails, nap on the hammock, play corn hole, take the beach chairs/toys to the private neighborhood beach, go to one of the many excellent restaurants, visit historic Stevensville, take a trip to Annapolis or DC, & so much more!

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay

Plan your getaway on the Chesapeake Bay! Blue Heron’s Landing is on beautiful Kent Island, MD. The home is a short walk from scenic waterways and beautiful biking and walking trails, and a quick drive to fantastic dining options and several Maryland’s best wedding venues. This hidden gem is just across the Bay Bridge from Annapolis and 1 hour from DC and Baltimore. It’s the perfect place to disconnect and recharge, or use as a launching point to explore more of Maryland’s Eastern Shore.

Find your quiet at The Creek House on Kent Island

Welcome to the Creek House on Kent Island! This cozy home is situated directly on Tolson Creek, which leads out to the Chesapeake Bay. The location of the home is both peaceful and serene, but also located within 20 minutes of shopping, wedding venues, water view restaurants, and more. Enjoy evening walks in the peaceful neighborhood, and end with a view of the sunset over the Bay at one of the two small neighborhood look outs (one includes a beach!).

Gorgeous Cottage: Easy Walk into St Michaels Town!

Gorgeous, sunny former artist loft with great views. Across from Miles River & harbor. Walk to town! Shopping, brewery, winery, museum, restaurants await! Located in historic Bentley Hay, the lodge is perfect for relaxing walks while runners and bikers explore spectacular sights, including the nearby St Michaels Nature Trail. Or rent a kayak and explore San Domingo Creek! NO PETS OR SMOKING. 4 GUESTS MAX BY LAW. Talbot Co License STR-716-KIM

Cottage on the Bay - Kent Island

Chesapeake Bay Waterfront home on Kent Island! Enjoy year round big sky and water views from the comfort of the screened porch & family room. Fish & crab from the pier or take a dip in the bay. Open concept living and rear bedroom/rec room are perfect for relaxing and having fun with family & friends. Close to popular wedding venues, local marinas & charter fishing boats, restaurants, Tiki bars, beaches, golfing, parks, & bike trails.