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
S$123
21 Sept - 22 Sept
includes taxes & fees
8/10 Very good! (1,000 reviews)
"Front desk and breakfast staff were friendly and amazing. Breakfast had good a variety of options. Housekeeping staff was rude. Extra blanket was dirty, otherwise the room was clean. Early morning renovations and construction was loud and woke us up."

Reviewed on 14 Sept, 2026

St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD
S$842
6 Oct - 7 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
S$366
5 Oct - 6 Oct
includes taxes & fees
9.8/10 Exceptional! (513 reviews)
"Great boutique hotel with a wonderful restaurant (Ruse). We stayed 3 nights and didn’t use our rental car until we checked out."

Reviewed on 13 Sept, 2026

The Wildset
See all 1,268 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 marina with several sailboats docked in calm waters.

St. Michaels Marina

Explore the waterfront in St. Michaels with a trip to St. Michaels Marina.
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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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Saint Michaels Town Hall

Located in the St. Michaels Historic District, this town hall adds charm to the area's preserved 19th-century architecture. Explore the surrounding brick pavements while discovering the town's rich maritime heritage.
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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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What to do in St. Michaels

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

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

S$343
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

S$378
per adult
St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

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

S$202
per adult
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
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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.

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.