Book Holiday Homes in Tilghman

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Featured Holiday Homes in Tilghman

The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach
Stay at this vacation home in North Beach. Enjoy free WiFi, a water park, and a garden. Popular attractions Bayside History Museum and Chesapeake Beach Water ...
The Blue Crab Beach House - Free beach passes
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

Stevensville
The price is NZ$407 per night from 22 Apr to 23 Apr
NZ$407
includes taxes & fees
22 Apr - 23 Apr
Stay at this vacation home in Stevensville. Enjoy free WiFi, a sauna, and a garden. Popular attractions Matapeake State Park and Paul Reed Smith Guitars are ...
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Modern Waterfront House with Amazing views!

Modern Waterfront House with Amazing views!

North Beach
Stay at this vacation home in North Beach. Enjoy a water park, a garden, and patios. Popular attractions Bayside History Museum and Chesapeake Beach Water Park ...
Modern Waterfront House with Amazing views!
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Sweet Bamboo Beach Cottage

Sweet Bamboo Beach Cottage

north beach
Stay at this vacation home in North Beach. Enjoy a beach locale, a water park, and a garden. Popular attractions Bayside History Museum and Chesapeake Beach ...
Sweet Bamboo Beach Cottage
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Deale
Stay at this vacation home in Deale. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Upper Yough River and Franklin Point State Park ...
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

St. Michaels
Stay at this vacation home in St. Michaels. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Muskrat Park and Higgins Yacht Yard and ...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Stunning  Chesapeake view from almost ever room, private  15 home community beach, fossils, 450 pier

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

Port Republic
Book a stay at this beach vacation home in Port Republic. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Matoaka Beach and Long Beach are ...
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2 out of 5
Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, a garden, and patios. Popular attractions Bay Ridge Beach and Annapolis Golf Club are located ...
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Grasonville
Stay at this vacation home in Grasonville. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Chesapeake Bay Environmental ...
Bay Breeze - Charming 3BR Waterfront Home on the Chester River
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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
Lowest Price
NZ$345
Highest Price
NZ$463
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, Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks, Bay Breeze - Charming 3BR Waterfront Home on the Chester River

Top trending hotels in Tilghman

Wylder Tilghman Island

Wylder Tilghman Island

2 out of 5
21551 Chesapeake Access Drive, Tilghman, MD
Fully refundableReserve now, pay when you stay
The price is NZ$345 per night from 27 Apr to 28 Apr
NZ$345
includes taxes & fees
27 Apr - 28 Apr
Stay at this hotel in Tilghman. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tilghman Watermen’s Museum and Talbot County Library Tilghman ...
Wylder Tilghman Island
The Tilghman Island Inn

The Tilghman Island Inn

3.5 out of 5
21384 Coopertown Rd, Tilghman, MD
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star inn in Tilghman. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Tilghman Island Inn
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3 out of 5
6176 Tilghman Island Road, Tilghman, MD
Fully refundableReserve now, pay when you stay
Stay at this 3-star hotel in Tilghman. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Knapp's Narrows Marina & Inn and Back Creek Community ...
Knapps Narrows Marina & Inn
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Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is NZ$463 per night from 6 May to 7 May
NZ$463
includes taxes & fees
6 May - 7 May
Stay at this 4-star beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Hyatt Regency Chesapeake Bay
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.