Stay If You Dare - Vacation Rentals in Phillips Wharf Environmental Center

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From US $1,361

         

10.0 (37 Reviews)

House

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

• Air Conditioner
• Parking
• Pool

• Maryland
• Sherwood

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From US $175

         

|

10.0 (1 Review)

House

St Michaels Area Cottage - Walk to Water and Marina

• Parking
• Pet Friendly
• Wheelchair Accessible

• Maryland
• Neavitt

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From US $316

         

|

9.0 (56 Reviews)

Bed & Breakfast

Black Walnut Point Inn

• Air Conditioner
• Parking
• Pool

• Maryland
• Tilghman

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From US $426

         

10.0 (35 Reviews)

House

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

• Air Conditioner
• Parking
• TV

• Maryland
• Tilghman

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From US $683

         

9.0 (1 Review)

House

Waterfront Bliss- Ultimate Tilghman Retreat home

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Tilghman

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From US $220

         

|

9.6 (119 Reviews)

Hotel

The Tilghman Island Inn

• Air Conditioner
• Parking
• Pool

• Maryland
• Tilghman

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From US $710

         

10.0 (22 Reviews)

House

Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!

• Air Conditioner
• Parking
• Pool

• Maryland
• Tilghman

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From US $275

         

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8.0 (1 Review)

House

Tilghman Island Retreat By Knapps Narrows!

• Parking
• Accessibility
• Security/Safety

• Maryland
• Tilghman

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From US $132

         

|

9.4 (358 Reviews)

Hotel

Knapps Narrows Marina & Inn

• Air Conditioner
• Parking
• Pool

• Maryland
• Tilghman

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From US $961

         

10.0 (20 Reviews)

House

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

• Air Conditioner
• Parking
• Pool

• Maryland
• Sherwood

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From US $596

         

10.0 (14 Reviews)

House

Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Neavitt

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From US $353

         

10.0 (14 Reviews)

Cottage

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Tilghman

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From US $276

         

10.0 (14 Reviews)

House

Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families

• Air Conditioner
• Parking
• TV

• Maryland
• Tilghman

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From US $428

         

10.0 (13 Reviews)

Cottage

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Tilghman

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From US $1,060

         

10.0 (11 Reviews)

House

Heated pool, sandy beach, pier, and playground set punch point apart!

• Air Conditioner
• Parking
• Pool

• Maryland
• Sherwood

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From US $284

         

10.0 (11 Reviews)

House

Pet-Friendly Tilghman Island Coastal Retreat

• Air Conditioner
• Parking
• TV

• Maryland
• Tilghman

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From US $600

         

10.0 (10 Reviews)

House

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Tilghman

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From US $357

         

10.0 (10 Reviews)

House

Charming 3BR Cottage in Heart of Tilghman Island – Bike everywhere!

• Air Conditioner
• Parking
• TV

• Maryland
• Tilghman

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From US $275

         

10.0 (9 Reviews)

House

Cozy 2-Bedroom Cottage on Tilghman Island – Near Restaurants & Water Activities

• Air Conditioner
• Parking
• TV

• Maryland
• Tilghman

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From US $293

         

10.0 (4 Reviews)

House

Tilghman Island Retreat By Knapps Narrows!

• Air Conditioner
• Parking
• TV

• Maryland
• Tilghman

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From US $358

         

9.8 (56 Reviews)

Cottage

The Middle Point Cabin in Saint Michaels

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Neavitt

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From US $432

         

9.8 (53 Reviews)

House

Stunning views at WATERFRONT St Michaels area historic home, dog friendly

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Neavitt

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From US $1,406

         

9.8 (40 Reviews)

House

ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACSnPET FRIENDLY

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Sherwood

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From US $414

         

9.8 (10 Reviews)

House

Bayfront Retreat Near St. Michaels | Private Dock Sunset Views

• Air Conditioner
• Parking
• TV

• Maryland
• Tilghman

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