Book Holiday Homes in Tilghman
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Featured Holiday Homes in Tilghman

The Blue Crab Beach House - Free beach passes

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Modern Waterfront House with Amazing views!

Sweet Bamboo Beach Cottage

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Your Annapolis Adventure Starts Here!!

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Tilghman Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Tilghman vacation homes are the perfect way for you to wing it.
Holiday houses in Tilghman let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Tilghman in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Tilghman adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Tilghman with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Tilghman vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Tilghman Holiday Homes essential information
Accommodation | 423 Holiday Homes |
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Lowest Price | NZ$289 |
Highest Price | NZ$494 |
Popular accommodation | The Blue Crab Beach House - Free beach passes , ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Modern Waterfront House with Amazing views!, Sweet Bamboo Beach Cottage, Rockhold Creek Cottage, Water Front, Vacation Home, Docks, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Your Annapolis Adventure Starts Here!! , Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks |
More accommodations in Tilghman
Top trending hotels in Tilghman

Wylder Tilghman Island

The Tilghman Island Inn

Knapps Narrows Marina & Inn

Hyatt Regency Chesapeake Bay
More ways to explore Tilghman
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.