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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
4,98 av 5 i genomsnittligt betyg, 204 omdömen
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.
4,97 av 5 i genomsnittligt betyg, 316 omdömen
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!
5,0 av 5 i genomsnittligt betyg, 70 omdömen
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.
4,99 av 5 i genomsnittligt betyg, 152 omdömen
Iconic Chesapeake. Unparalleled Luxury.
Autumn at The Cottage at Silver Water is peaceful, cozy, and a little magical. Crisp days invite you to kayak, explore the shoreline, or enjoy the changing colors. Evenings bring golden skies, spectacular sunsets, cool breezes, and fires by the water. Inside, the cottage is warm and inviting, with luxurious bedding, curated art, and thoughtful amenities for a relaxed, memorable stay. Come experience autumn at Silver Water—and see why every guest has given their stay five stars.
5,0 av 5 i genomsnittligt betyg, 217 omdömen
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.
4,98 av 5 i genomsnittligt betyg, 162 omdömen
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.
5,0 av 5 i genomsnittligt betyg, 54 omdömen
Private & Peaceful Water Views, Big Deck, Games
Down a gravel drive, surrounded by trees, with no neighbors in sight and water views from the deck. This home was renovated top to bottom and furnished new throughout. Three bedrooms and three full baths. The upper level runs from a fireplace living room through the kitchen to a vaulted, skylit dining room. Downstairs: a pool table. Outside: a big deck with water views, a screened porch, and a fire pit. 15 minutes to the Bay Bridge and the local wedding venues.
5,0 av 5 i genomsnittligt betyg, 7 omdömen
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.
4,99 av 5 i genomsnittligt betyg, 371 omdömen
The Little Anchor Cottage, St. Michaels, MD
Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.
4,97 av 5 i genomsnittligt betyg, 303 omdömen
Waterfront cottage in Wittman Maryland
Relax at this charming 2-bedroom waterfront cottage in Wittman, MD. Enjoy peaceful water views, direct shoreline access, and classic Eastern Shore charm. Perfect for couples or small families, the cottage features cozy bedrooms, a comfortable living area, and a fully equipped kitchen. Ideal for kayaking, paddle boarding, crabbing, fishing, or simply unwinding by the water near local marinas and seafood spots. Talbot County rental license #STN-25-19
4,96 av 5 i genomsnittligt betyg, 24 omdömen
Coastal Waterfront 1 Bedroom Cottage
Enjoy a peaceful waterfront getaway just 2 miles from Historic Downtown Annapolis and the U.S. Naval Academy. Located directly on the South River in a quiet neighborhood, this charming cottage features a full kitchen, 1 bedroom, washer/dryer, and sleeper sofa for up to 4 guests. Relax on the private patio with outdoor seating, grill, and fire pit, or enjoy the beautiful river views. Perfect for exploring Annapolis or simply unwinding by the water.
5,0 av 5 i genomsnittligt betyg, 226 omdömenPopulära bekvämligheter för semesterboenden i McDaniel
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Punch Point boasts a sandy beach w/ pool and pier
5,0 av 5 i genomsnittligt betyg, 26 omdömen
*Waterfront* 5BR w/ Pool + Firepit on Kent Island!
5,0 av 5 i genomsnittligt betyg, 23 omdömen
Private&Cozy/3br+2ba/1mi to town
4,94 av 5 i genomsnittligt betyg, 89 omdömen
Kent Island Waterfront | Swim Spa + Sauna + Beach
5,0 av 5 i genomsnittligt betyg, 28 omdömen
Ahoy St. Michaels! - A Historic Retreat
5,0 av 5 i genomsnittligt betyg, 65 omdömen
Secluded water, private sitting room, full bath!
5,0 av 5 i genomsnittligt betyg, 47 omdömen
The Getaway
5,0 av 5 i genomsnittligt betyg, 36 omdömen
Heron Roost
5,0 av 5 i genomsnittligt betyg, 96 omdömenDestinationer att utforska
- New York City Semesterboenden
- Philadelphia Semesterboenden
- Washington, D.C. Semesterboenden
- Ocean City Semesterboenden
- Pittsburgh Semesterboenden
- Raleigh Semesterboenden
- Virginia Beach Semesterboenden
- Jersey City Semesterboenden
- Newark Semesterboenden
- Baltimore Semesterboenden
- Richmond Semesterboenden
- Atlantic City Semesterboenden
- M&T Bank Stadium
- National Mall
- Vita huset
- Walter E Washington Convention Center
- Nationalparken
- Johns Hopkinsuniversitetet
- FedExField
- Oriole Park at Camden Yards
- Federal Hill Park
- Capital One Arena
- Georgetown Waterfront Park
- Howard University
- Arlington National Cemetery
- Betterton Beach
- Washingtonmonumentet
- Dover Motor Speedway
- National Harbor
- Nationalmuseum för afroamerikansk historia och kultur
- Baltimore Convention Center
- CFG Bank Arena
- Smithsonian National Zoological Park
- Bibelmuseet
- Smithsonian National Air and Space Museum
- Nationella akvariet





