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Featured Holiday Homes in Tilghman

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing
This vacation home is 3.1 mi (5 km) from Upper Yough River and 4.8 mi (7.7 km) from Bayside History Museum.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Cambridge
With a stay at this vacation home in Cambridge, you'll be on the waterfront, and 6.3 mi (10.2 km) from Ragged Island and 7.7 mi (12.4 km) from Spocott ...
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Walk to Everything House

Walk to Everything House

Saint Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.
Walk to Everything House
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Brand New Spacious Luxury Home

Brand New Spacious Luxury Home

Annapolis
With a stay at this vacation home in Annapolis, you'll be within a 5-minute drive of U.S. Naval Academy and Spa Creek.
Brand New Spacious Luxury Home
Circa 1700 Chesapeake Colonial home on the National Register.

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville
Located in Stevensville, this vacation home is on the waterfront, a 1-minute drive from Matapeake State Park and 6 minutes from Paul Reed Smith Guitars.
Circa 1700 Chesapeake Colonial home on the National Register.
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

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

Stevensville
The price is AU$395 per night from 26 Feb to 27 Feb
AU$395
includes taxes & fees
26 Feb - 27 Feb
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!❤️
Waterfront Cheerful 6 BR Home with Private Pier

Waterfront Cheerful 6 BR Home with Private Pier

Edgewater
Located in Edgewater, this vacation home is on the waterfront, within a 10-minute drive of South River Golf Links and London Town.
Waterfront Cheerful 6 BR Home with Private Pier
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2 out of 5
Cambridge
Located in Cambridge, this vacation home is within a 15-minute walk of Harriet Tubman Museum and Educational Center and Richardson Maritime Museum.
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Serene waterfront sunsets in this sprawling historic Annapolis home

Serene waterfront sunsets in this sprawling historic Annapolis home

Annapolis
With a stay at this vacation home in Annapolis (Hillsmere), you'll be within a 15-minute drive of U.S. Naval Academy and Maryland Quiet Waters Park.
Serene waterfront sunsets in this sprawling historic Annapolis home
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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
332 Holiday Homes
Lowest Price
AU$293
Highest Price
AU$634
Popular accommodation
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, Walk to Everything House, Brand New Spacious Luxury Home, Circa 1700 Chesapeake Colonial home on the National Register., ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Waterfront Cheerful 6 BR Home with Private Pier, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, Serene waterfront sunsets in this sprawling historic Annapolis home

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$293 per night from 25 Feb to 26 Feb
AU$293
includes taxes & fees
25 Feb - 26 Feb
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$303 per night from 6 Mar to 7 Mar
AU$303
includes taxes & fees
6 Mar - 7 Mar
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$430 per night from 25 Feb to 26 Feb
AU$430
includes taxes & fees
25 Feb - 26 Feb
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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Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is AU$634 per night from 26 Feb to 27 Feb
AU$634
includes taxes & fees
26 Feb - 27 Feb
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, steps from Perry Cabin Park and 8 minutes by foot from Higgins Yacht Yard and Marina.
Inn at Perry Cabin
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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.