Tilghman Holidays

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Top hotels in Tilghman

The Tilghman Island Inn

The Tilghman Island Inn

3.5 out of 5
21384 Coopertown Rd Tilghman MD
The price is S$320 per night from 20 Jul to 21 Jul
S$320
20 Jul - 21 Jul
includes taxes & fees
9.4/10 Exceptional! (140 reviews)
"Nice spot with access to downtown St Michaels. The only unfortunate part of our stay was the restaurant was closed for renovations. Staff was kind and helpful during our stay and the room was very clean. Property right on the canal; so perfect for boaters too!! Also- dog friendly, we appreciated ..."

Reviewed on 30 Jun, 2026

The Tilghman Island Inn
Wylder Tilghman Island

Wylder Tilghman Island

2 out of 5
21551 Chesapeake Access Drive Tilghman MD
The price is S$578 per night from 6 Jul to 7 Jul
S$578
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (98 reviews)
"Property and the grounds were really beautiful and well maintained. Rooms were somewhat small, but there were so many outdoor places to hang out it was not a problem."

Reviewed on 27 Jun, 2026

Wylder Tilghman Island
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
The price is S$500 per night from 7 Jul to 8 Jul
S$500
7 Jul - 8 Jul
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Dealing with billing issue. Other than that, great place to stay."

Reviewed on 26 Jun, 2026

Hyatt Regency Chesapeake Bay
See all 768 properties in Tilghman
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.

Stay near popular Tilghman attractions

Tilghman Watermen’s Museum

9.8/10 (6 reviews)
This waterfront museum chronicles Tilghman Island's maritime heritage through artefacts and oral histories. Explore a replica crab shanty and join weekend guided tours for insights into watermen's traditions.
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Frequently asked questions

How much does a Tilghman holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Tilghman costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Tilghman?
December, January and February are the best times to look for cheap Tilghman holiday packages. Opting to travel in quieter months means you can usually find lower prices on flights and accommodation.
How many days is enough for Tilghman?
The ideal length for your Tilghman holiday depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to hit all the main sights and explore some hidden treasures along the way.
How to find the best Tilghman package deals?
Start your search for a Tilghman package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Tilghman package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Tilghman adventure off to a flying start.
Is it cheaper to book a Tilghman holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still get the flexibility to create a customised Tilghman holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Tilghman?
If you have your Tilghman holiday dates locked in, book as early as you can to bag some fantastic deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Tilghman?

  1. Pick your dates: The things you want to do in Tilghman and your favourite season can help you decide when to get away.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and experiences. Your hotel will probably be the biggest expense during your trip to Tilghman.
  3. Set the duration of your trip: Start by listing all the sights and activities you'd like to get to in Tilghman. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Tilghman holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.