Book Holiday Homes in Tilghman

May 2025

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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
Located in North Beach, this vacation home is by the sea, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
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 AU$488 per night from 18 May to 19 May
AU$488
18 May - 19 May
includes taxes & fees
Located in Stevensville, this vacation home is a 4-minute drive from Matapeake State Park and 7 minutes from Paul Reed Smith Guitars.
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Modern Waterfront House with Amazing views!

Modern Waterfront House with Amazing views!

North Beach
Located in North Beach, this vacation home is on the waterfront, within a 5-minute drive of 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
When you stay at this vacation home in North Beach, you'll be on the beach, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water ...
Sweet Bamboo Beach Cottage
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Deale
With a stay at this vacation home, you'll be centrally located in Deale, within a 10-minute drive of 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
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Muskrat Park.
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
Located in Port Republic, this vacation home is on the waterfront, within a 10-minute drive of R&J's PlayPark and calvART Gallery.
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
With a stay at this vacation home in Annapolis (Oyster Harbor), you'll be within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping ...
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
When you stay at this vacation home in Grasonville, you'll be within a 10-minute drive of Chesapeake Exploration Center and Queenstown Premium Outlets.
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
427 Holiday Homes
Lowest Price
AU$247
Highest Price
AU$497
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 AU$377 per night from 19 May to 20 May
AU$377
19 May - 20 May
includes taxes & fees
When you a stay at Wylder Tilghman Island in Tilghman, you'll be on the waterfront, within a 5-minute walk of Tilghman Watermen’s Museum and Talbot County Library ...
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
The price is AU$386 per night from 12 May to 13 May
AU$386
12 May - 13 May
includes taxes & fees
With a stay at The Tilghman Island Inn in Tilghman, you'll be a 1-minute walk from Tilghman Island Marina and 7 minutes by foot from Knapp's Narrows Marina & ...
The Tilghman Island Inn
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$497 per night from 3 Jun to 4 Jun
AU$497
3 June - 4 June
includes taxes & fees
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 6 minutes from Dorchester County Visitors ...
Hyatt Regency Chesapeake Bay
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Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
Fully refundableReserve now, pay when you stay
The price is AU$247 per night from 27 May to 28 May
AU$247
27 May - 28 May
includes taxes & fees
Located in Grasonville, Hyatt Place Kent Narrows & Marina is in the historical district, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from ...
Hyatt Place Kent Narrows & Marina
Don't see what you're looking for?
See all available properties in Tilghman
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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.