St. Michaels Holidays

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Top hotels in St. Michaels

St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
€91
20 Sept - 21 Sept
includes taxes & fees
8/10 Very good! (1,001 reviews)
"I am very hard pressed to recommend this hotel to anyone - biggest issue was cleanliness. This summarizes my conversation with manager at check out. Their response: NO payment adjustment - booked thru 3rd party. The only plus for this Inn was its proximity to St. Michaels’ town center, noting that ..."

Reviewed on 17 Sept 2026

St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD
€578
13 Oct - 14 Oct
includes taxes & fees
9.6/10 Exceptional! (402 reviews)
"It’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way."

Reviewed on 8 Sept 2026

Inn at Perry Cabin
The Wildset

The Wildset

209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
€251
5 Oct - 6 Oct
includes taxes & fees
The Wildset
See all 1,276 properties in St. Michaels
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 St. Michaels attractions

A lighthouse on stilts with a green roof, surrounded by water and greenery.
Photo by Louise Johnson

Chesapeake Bay Maritime Museum

9.4/10 (91 reviews)
Explore maritime heritage at this waterfront museum featuring the historic Hooper Strait Lighthouse and indigenous Chesapeake Bay watercraft. Watch shipwrights craft vessels while enjoying Miles River views.
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A white wooden house with a brown door and a small window.

Saint Michaels Village

This historic waterfront town showcases Maryland's maritime heritage through preserved colonial architecture. Explore the Maritime Museum or enjoy fresh seafood while watching sailboats glide across the harbour.
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St. Michaels Winery

8.6/10 (91 reviews)
Sample the Eastern Shore's finest wines in this historic Old Mill District winery. Enjoy guided tastings of 18 handcrafted varieties while learning about Maryland's unique terroir.
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1879 Hooper Straight Lighthouse

This rare screwpile lighthouse, relocated from Chesapeake Bay, offers a glimpse into 19th-century maritime life. Climb the spiral staircase to the lantern room for sweeping bay views and authentic keeper's quarters.
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Perry Cabin Park

This 9.5-acre community space offers well-maintained sports fields and a playground for active recreation. Enjoy a peaceful picnic in the pavilion or join a local baseball game in this serene St. Michaels gathering spot.
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St Michaels Nature Trail

You can take time to visit St Michaels Nature Trail during your travels to St. Michaels.
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St. Michaels Museum

8.6/10 (9 reviews)
Step into three restored 19th-century buildings that reveal the rich history of this Chesapeake Bay town. Explore exhibits on Frederick Douglass's local connections through walking tours of historic St. Michaels.
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Windon Distilling

LYON RUM crafts small-batch American spirits in a historic St. Michaels mill using traditional methods. Sample their handcrafted rums in the welcoming tasting room while learning about their cane-to-glass process.
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What to do in St. Michaels

St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

€137
per adult
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

€232
per adult
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany

St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany

€256
per adult
St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany
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Frequently asked questions

How much does a St. Michaels holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday to St. Michaels costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to St. Michaels?
January, February and March are great times to search for cheap St. Michaels holiday packages. Travelling in quieter periods means you can typically find better prices on accommodation and flights.
How many days is enough for St. Michaels?
With a well-organised travel plan, you can easily visit the main St. Michaels sights in a handful of days. But if you want to venture off the beaten track or go on day tours, consider booking your St. Michaels holiday for longer.
Is it worth booking a holiday package to St. Michaels?
Well known for its watersports, culture and nature, a St. Michaels holiday is a hit with all kinds of travellers. Be sure to check out key sights like Chesapeake Bay Maritime Museum and St. Michaels Museum, and consider renting a set of wheels for day trips to experience even more.
How to find the best St. Michaels package deals?
Use Expedia's filters to find some fabulous St. Michaels package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for St. Michaels package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a St. Michaels holiday as a package?
You can enjoy significant savings on your next St. Michaels escape by booking a tailored holiday package. Check the "Package" heading, then enter your destination and travel dates to see some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to St. Michaels?
Land fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu St. Michaels break.
How to plan a trip to St. Michaels?
  1. Choose when to get away: Check your diary and get packing. Your favourite season and the available activities will also help you decide when to escape to St. Michaels.
  2. Plan your budget wisely: As well as the price of your hotel, you'll need to factor in other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected expenses that may arise during your trip to St. Michaels.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in St. Michaels. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised St. Michaels holiday package.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.