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- Apartment in St. Michaels – Walk to Everything! – 2 Bedroom Vacation Rental in Saint Michaels, Maryland
- Bald Eagle Point Estate | Dock, Firepit & Beach – 6 Bedroom Vacation Rental in Sherwood, Maryland
- Bayfront Escape Tilghman Island | Sunset Views – 3 Bedroom Vacation Rental in Tilghman, Maryland
- Charming 2 Bedroom Cottage on Tilghman Island – 2 Bedroom Vacation Rental in Tilghman, Maryland
- Charming Tilghman Cottage | Pet Friendly – 3 Bedroom Vacation Rental in Tilghman, Maryland
- Charming Tilghman Island Cottage | Pets Welcome – 3 Bedroom Vacation Rental in Tilghman, Maryland
- Combsberry – Private Waterfront Estate – 5 Bedroom Vacation Rental in Oxford, Maryland
- Downtown St. Michaels | Porch + Pet-Friendly – 1 Bedroom Vacation Rental in Saint Michaels, Maryland
- Downtown St. Michaels | Porch + Pet-Friendly – 3 Bedroom Vacation Rental in Saint Michaels, Maryland
- Downtown St. Michaels Studio | Walk Everywhere – Studio Vacation Rental in Saint Michaels, Maryland
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- Eastern Shore Cottage – Near St. Michaels Gateway – 3 Bedroom Vacation Rental in Wittman, Maryland
- Pet-Friendly Cottage | Near St. Michaels – 2 Bedroom Vacation Rental in Neavitt, Maryland
- Saint Michaels Retreat with Kayaks & Bikes – 2 Bedroom Vacation Rental in Saint Michaels, Maryland
- St. Michaels Escape | Pool, Hot Tub & Fire Pit – 3 Bedroom Vacation Rental in Saint Michaels, Maryland
- St. Michaels Stay | Walking Distance to Downtown – 3 Bedroom Vacation Rental in Saint Michaels, Maryland
- St. Michaels Waterfront Retreat | Near Downtown – 4 Bedroom Vacation Rental in Saint Michaels, Maryland
- Tilghman Island Cottage – Pets Welcome! – 3 Bedroom Vacation Rental in Tilghman, Maryland
- Tilghman Island Waterfront | Private Dock – 4 Bedroom Vacation Rental in Tilghman, Maryland
- Tranquility on Tilghman Island – Wide Water Views – 5 Bedroom Vacation Rental in Tilghman, Maryland
- Vintage Pet-Friendly Cottage | Tilghman Island – 2 Bedroom Vacation Rental in Tilghman, Maryland
- Walk to Downtown St. Michaels | Pet Friendly – 3 Bedroom Vacation Rental in Saint Michaels, Maryland
- Waterfront | Pet Friendly & Close to St. Michaels – 4 Bedroom Vacation Rental in Bozman, Maryland
- Waterfront Escape - Bay Views & Near Annapolis – 3 Bedroom Vacation Rental in Stevensville, Maryland
- Waterfront Home | Wedding & Family Getaways – 4 Bedroom Vacation Rental in Easton, Maryland
- Waterfront Paradise | Pool, Views & Serenity – 4 Bedroom Vacation Rental in Royal Oak, Maryland
- Waterfront Retreat | Near St. Michaels & Tilghman – 4 Bedroom Vacation Rental in Sherwood, Maryland
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