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
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels
Stay at this vacation home in St. Michaels. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Muskrat Park and Clint S. Bradley Park are ...
Dollhouse in Central Historic St Michaels
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford
Stay at this vacation home in Woolford. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Woods Island and Harriet Tubman Underground Railroad ...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
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Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
Stay at this vacation home in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Choptank River Lighthouse and Long Wharf Park ...
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Adorable waterside cottage with pool Beach community

Adorable waterside cottage with pool Beach community

Edgewater
Stay at this vacation home in Edgewater. Enjoy private pools, laundry facilities, and patios. Popular attractions Sand Point Marsh and Triton Beach are located ...
Adorable waterside cottage with pool Beach community
Beach Home with King Bed and Beach Passes in a Cute Town

Beach Home with King Bed and Beach Passes in a Cute Town

North Beach
Book a stay at this family-friendly vacation home in North Beach. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Bayside History Museum ...
Beach Home with King Bed and Beach Passes in a Cute Town
Rising Sun Bay View Cottage

Rising Sun Bay View Cottage

Chesapeake Beach
Book a stay at this beach vacation home in Chesapeake Beach. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions Bruce Gabrielson's Surf ...
Rising Sun Bay View Cottage
Private Cottage on gated estate

Private Cottage on gated estate

Annapolis
Stay at this vacation home in Annapolis. Enjoy laundry facilities, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Annapolis City ...
Private Cottage on gated estate
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Trappe
Stay at this vacation home in Trappe. Enjoy private pools, a garden, and laundry facilities. Popular attractions The Third Haven Friends Meeting House and Academy ...
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
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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
425 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
The Blue Crab Beach House - Free beach passes , Dollhouse in Central Historic St Michaels, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, Adorable waterside cottage with pool Beach community, Beach Home with King Bed and Beach Passes in a Cute Town, Rising Sun Bay View Cottage, Private Cottage on gated estate, Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

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
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
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
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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Black Walnut Point Inn

Black Walnut Point Inn

3.5 out of 5
4417 Black Walnut Point Road, Tilghman, MD
Stay at this 3.5-star B&B in Tilghman. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tilghman Watermen’s Museum and Talbot County Library ...
Black Walnut Point Inn
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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.

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^Subject to availability and chosen travel dates.