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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.

La Casita on Harris Creek, St. Michaels

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

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.

The Pool House in Romancoke On The Bay

Spacious 4 bedroom home on Kent Island minutes from multiple wedding venues. Inground pool with sunny & shaded sitting areas for everyone to enjoy. Pergola brick patio w/table & a deck with a bar for outdoor meals and a fully fenced back yard for your dog. Additional fee per dog. Living room with Fireplace, Sunny family room, nicely equipped Kitchen, all just a block from the Eastern Bay if you have beach strolling, kayaking or paddle boarding in mind. South Island Bike Trail just a block away.

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.

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.

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!

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.

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!

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Serene Hideaway

Welcome to your perfect escape — a newly remodeled, tranquil, tasteful space nestled just minutes from downtown Annapolis and the Naval Academy. Whether you're here for business or pleasure, our serene hideaway offers the best of both worlds: central convenience with quiet living. Wake up to natural light, sip your morning coffee (or tea!), and unwind in peaceful surroundings after a day of exploring the city.

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.