St. Michaels Vacations from $1,145

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Your St. Michaels Vacation

The fascinating city of St. Michaels is calling your name. Immerse yourself in everything it has to offer with a St. Michaels vacation package that's tailored to you. You'll want to take in some sights during your trip to St. Michaels. Drop by major attractions such as St. Michaels Winery, Chesapeake Bay Maritime Museum and St. Michaels Museum. Stop daydreaming and start doing. Browse the many options on Expedia today and finally put your St. Michaels vacation plans in motion!

The Latest St. Michaels vacation packages

Price found within the past 48 hours. Click for updated prices.
Americas Best Value Inn Princess Anne

Americas Best Value Inn Princess Anne

$1,145
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
7/10 Good! (74 reviews)
Very pleasant stay look forward to staying again

Reviewed on Aug 20, 2026

Beach Walk

Beach Walk

Downtown Ocean City
Save 100% on your flight
$1,622
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
7.6/10 Good! (113 reviews)
Parking was easy if they had spots.

Reviewed on Aug 20, 2026

Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

$1,296
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8.8/10 Excellent! (167 reviews)
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

Midtown Ocean City
$1,352
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8.2/10 Very Good! (1,022 reviews)
Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

Downtown Ocean City
$1,553
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
9/10 Wonderful! (1,036 reviews)
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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 harbor.
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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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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 sidewalks while discovering the town's rich maritime heritage.
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What to do in St. Michaels

Epiphany

2 Hour Chesapeake Day Sail on Catamaran Epiphany

$245
per adult
2 Hour Chesapeake Day Sail on Catamaran Epiphany
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

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

$159
per adult
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
2-Hour Relaxing Chesapeake Day Sail on Lady Patty

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

$160
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
See all activities in St. Michaels

St. Michaels Hotel Deals

St Michaels Inn

St Michaels Inn

1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
$89 nightly
$98 total
Aug 31 - Sep 1
Total with taxes and fees
8/10 Very Good! (1,010 reviews)
"-"

Reviewed on Aug 27, 2026

St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD
$445 nightly
$489 total
Sep 7 - Sep 8
Total with taxes and fees
Inn at Perry Cabin
The Wildset

The Wildset

209 N Talbot St St. Michaels MD
Fully refundableReserve now, pay when you stay
$262 nightly
$288 total
Sep 15 - Sep 16
Total with taxes and fees
The Wildset
See all 1,266 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.

Find the Best St. Michaels Vacation Packages

Things to do in and around St. Michaels

St. Michaels, Maryland offers a charming blend of outdoor activities and scenic beauty, perfect for a relaxing vacation. Enjoy the boardwalk and recreational areas while taking in the picturesque surroundings. Popular activities include boat tours, sailing adventures, private tours, and sunset cruises, allowing you to explore the area's rich maritime heritage and stunning waterfront views.

Shopping

In St. Michaels, you can shop at Saint Michaels Village for a charming local experience. For more options, Easton Cycle and Sport is nearby, only 9 miles away. If you're up for a drive, Queenstown Premium Outlets offers a wide variety of shops, located 14 miles from St. Michaels.

Recreation

At Avalon Theatre, enjoy captivating performances in a charming atmosphere that promotes romance and family fun, just 8 miles from St. Michaels. Experience rejuvenation at Talbot Massage, where relaxation is key, located 9 miles away. For outdoor enthusiasts, Queenstown Harbor Golf Club offers a scenic golfing experience, 14 miles from St. Michaels.

Adventure

Chesapeake Beach Water Park offers thrilling water slides and family-friendly fun, located 18 miles from St. Michaels. For water sports enthusiasts, Annapolis Sailing School provides exciting sailing experiences in the open water. If you prefer hiking, the B&A Trail, 28 miles away, showcases breathtaking scenery and outdoor adventure.

Nightlife

St. Michaels offers a charming nightlife with local favorites like the Crab Claw Restaurant for fresh seafood and waterfront views. For a cozy pub vibe, visit the Eastern Shore Brewing Company, where you can enjoy craft beers and live music. The atmosphere is relaxed and inviting, perfect for unwinding after a day of exploration.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around St. Michaels

St. Michaels, Maryland, offers a delightful blend of outdoor adventures and cultural experiences. Visitors can explore scenic marinas, fascinating museums, and tranquil urban parks, perfect for families and culture enthusiasts alike. Don’t miss the stunning views along the Miles River, which enhances the charm of this picturesque town. Whether you're looking to relax on the beach or immerse yourself in local history, St. Michaels has something for everyone.

  • Chesapeake Bay Maritime Museum: Explore the rich maritime heritage of the Chesapeake Bay at this interactive museum located in St. Michaels. With engaging exhibits and historic vessels, you'll gain insights into the region's boating, fishing, and waterman traditions.
  • St. Michaels Museum: Delve into local history at this charming museum, which showcases the town’s past through artifacts, photographs, and stories. Located in the heart of St. Michaels, it offers a glimpse into the community's evolution and maritime connections.
  • Pickering Creek Audubon Center: Situated 7 miles from St. Michaels, this environmental center promotes conservation and eco-friendly practices. Enjoy scenic trails and diverse wildlife, making it an ideal spot for birdwatching and nature walks.

Best time to go to St. Michaels

The best time to visit St. Michaels can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in St. Michaels falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in St. Michaels falls in January, visitor numbers are moderately low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January36.3°F (2.4°C)Light RainMostly SunnyModerately LowSlightly Low
February38.8°F (3.8°C)Light RainMostly SunnyAverageSlightly Low
March45.3°F (7.4°C)Light RainMostly SunnyAverageSlightly Low
April55.6°F (13.1°C)Light RainMostly SunnyModerately HighAverage
May64.6°F (18.1°C)Light RainMostly SunnyAverageAverage
June73.4°F (23.0°C)Light RainMostly SunnyModerately HighSlightly High
July78.4°F (25.8°C)Light RainMostly SunnyModerately HighAverage
August76.8°F (24.9°C)Light RainMostly SunnyAverageAverage
September71.1°F (21.7°C)Light RainMostly SunnyAverageSlightly High
October61.0°F (16.1°C)Light RainMostly SunnyAverageSlightly High
November49.5°F (9.7°C)Light RainMostly SunnyModerately LowAverage
December42.3°F (5.7°C)Light RainMostly SunnyModerately LowAverage

Tips to save on your trip to St. Michaels

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to St. Michaels.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

St. Michaels Essential Information

Language
English
Currency
U.S dollars
Population
1,050
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
St. Michaels Winery, Avalon Theatre and Historical Society of Talbot County

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Frequently asked questions

How much does a St. Michaels vacation package cost?
You can snap up a vacation package to this destination from $1,145 on Expedia. However, how much your vacation 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?
You can typically find lower prices and greater availability in January, September and December. Browse our cheap St. Michaels vacation packages and you could land some excellent off-season deals.
How many days is enough for St. Michaels?
The ideal duration of your St. Michaels vacation depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to go to all the main sights and discover some hidden spots along the way.
Is it worth booking a vacation package to St. Michaels?
St. Michaels has all the ingredients you need for a fantastic trip — nature, culture and watersports are just the start. Whether you want to visit attractions like Chesapeake Bay Maritime Museum and St. Michaels Museum, or take the path less traveled, you'll have plenty to do on your St. Michaels vacation.
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 vacation package as soon as possible.
Is it cheaper to book a St. Michaels vacation as a package?
You can enjoy significant savings on your next St. Michaels escape by booking a tailored vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later St. Michaels vacation packages?
Set off on your ideal getaway to St. Michaels with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or wait until your next paycheck — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up cheap deals before they disappear.

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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.