Book Holiday Homes in Tilghman

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Featured Holiday Homes in Tilghman

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD
When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
"La Licorne" Waterfront Beach Cottage

"La Licorne" Waterfront Beach Cottage

North Beach MD
With a stay at this vacation home in North Beach, you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new window"La Licorne" Waterfront Beach Cottage
The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach MD
With a stay at this vacation home in Owings, you'll be within a 5-minute drive of Chesapeake Bay and Bayside History Museum.
Opens in a new windowThe Cozy Crab- Your Charming Haven in Lovely North Beach!
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Kent Island Luxary Home W/ Pool and walking distance from the beach

Kent Island Luxary Home W/ Pool and walking distance from the beach

Stevensville MD
The price is AU$1,713 per night from 18 May to 19 May
AU$1,713
18 May - 19 May
includes taxes & fees
With a stay at this vacation home in Stevensville, you'll be within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowKent Island Luxary Home W/ Pool and walking distance from the beach
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville MD
The price is AU$526 per night from 1 June to 2 June
AU$526
1 June - 2 June
includes taxes & fees
With a stay at this vacation home in Stevensville, you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowRelax on Kent Island in a 4 Bedroom Home w/Waterview!
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge MD
With a stay at this vacation home in Cambridge, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Spocott Windmill.
Opens in a new windowWaterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Shady Side MD
With a stay at this vacation home in Shady Side, you'll be within a 10-minute drive of Chesapeake Bay and Shadyside Park.
Opens in a new windowLovely bay views with kayaks, bikes, fire pit, crabbing & more
The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach MD
When you stay at this vacation home in North Beach, you'll be by the sea, within a 10-minute walk of Chesapeake Bay and Bayside History Museum.
Opens in a new windowThe Blue Crab Beach House - Free beach passes
Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Edgewater MD
The price is AU$504 per night from 25 May to 26 May
AU$504
25 May - 26 May
includes taxes & fees
Located in Edgewater, this vacation home is within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay.
Opens in a new windowCharming 3-bedroom house with AC, WiFi in tranquil Edgewater on the 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.

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
396 Holiday Homes
Lowest Price
AU$385
Highest Price
AU$1,713
Popular accommodation
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, "La Licorne" Waterfront Beach Cottage, The Cozy Crab- Your Charming Haven in Lovely North Beach!, Kent Island Luxary Home W/ Pool and walking distance from the beach, Relax on Kent Island in a 4 Bedroom Home w/Waterview!, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, Lovely bay views with kayaks, bikes, fire pit, crabbing & more, The Blue Crab Beach House - Free beach passes , Charming 3-bedroom house with AC, WiFi in tranquil Edgewater on the bay .

Top trending hotels in Tilghman

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
The price is AU$385 per night from 19 May to 20 May
AU$385
19 May - 20 May
includes taxes & fees
With a stay at The Tilghman Island Inn in Tilghman, you'll be within a 5-minute walk of Chesapeake Bay and Tilghman Island Marina.
Opens in a new windowThe Tilghman Island Inn
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 AU$597 per night from 31 May to 1 June
AU$597
31 May - 1 June
includes taxes & fees
When you stay at Wylder Tilghman Island in Tilghman, you'll be on the waterfront, within a 10-minute walk of Chesapeake Bay and Tilghman Watermen’s Museum.
Opens in a new windowWylder Tilghman Island
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD
When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Save an average of 15% on thousands of hotels when you're signed in
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 AU$416 per night from 26 May to 27 May
AU$416
26 May - 27 May
includes taxes & fees
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 5 minutes from Eastern Shore Hospital ...
Opens in a new windowHyatt 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.

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^Subject to availability and chosen travel dates.