St. Michaels Vacation Packages 2026 from $674

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.

Fenwick Shores, Tapestry Collection by Hilton

$674

per person

Dec 5 - Dec 12

found 3 hours ago

Roundtrip non-stop flight included

San Juan (SJU) to Salisbury (SBY)

9.4/10 Exceptional! (858 reviews)

Bay Club Resort by Coolvacay

Midtown Ocean City

$1,148

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Salisbury (SBY)

8.4/10 Very Good! (56 reviews)

Been here many times - great place to stay.

Reviewed on Oct 9, 2026

Princess Royale Oceanfront Resort

North Ocean City

$784

per person

Dec 5 - Dec 12

found 3 hours ago

Roundtrip non-stop flight included

San Juan (SJU) to Salisbury (SBY)

8.8/10 Excellent! (2,809 reviews)

Our stay was excellent, definitely will go back!

Reviewed on Oct 13, 2026

Bethany Beach Ocean Suites Residence Inn by Marriott

Downtown Bethany Beach

$1,407

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Salisbury (SBY)

9/10 Wonderful! (870 reviews)

The Shore House

West Ocean City

$3,286

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Salisbury (SBY)

6.6/10 (819 reviews)

This place is the best bargain at the Beach!

Reviewed on Oct 12, 2026

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Stay near popular St. Michaels attractions

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

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 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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St Michaels Nature Trail

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

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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 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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Muskrat Park

After visiting Muskrat Park, make a plan to see the other sights and activities in St. Michaels.

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What to do in St. Michaels

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

$159

per adult

2 Hour Chesapeake Day Sail on Catamaran Epiphany

$245

per adult

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

$270

per adult

See all activities in St. Michaels

St. Michaels Hotel Deals

St Michaels Inn

1228 S Talbot Street St. Michaels MD

Fully refundableReserve now, pay when you stay

$89 nightly

$98 total

Nov 1 - Nov 2

Total with taxes and fees

8/10 Very Good! (1,000 reviews)

"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help ..."

Reviewed on Oct 13, 2026

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

$513 nightly

$564 total

Nov 9 - Nov 10

Total with taxes and fees

The Wildset

209 N Talbot St St. Michaels MD

$252 nightly

$277 total

Nov 3 - Nov 4

Total with taxes and fees

See all 1,274 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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	36.3°F (2.4°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
February	38.8°F (3.8°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	45.3°F (7.4°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	55.6°F (13.1°C)	Light Rain	Mostly Sunny	Moderately High	Average
May	64.6°F (18.1°C)	Light Rain	Mostly Sunny	Average	Average
June	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
July	78.4°F (25.8°C)	Light Rain	Mostly Sunny	Moderately High	Average
August	76.8°F (24.9°C)	Light Rain	Mostly Sunny	Average	Average
September	71.1°F (21.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	61.0°F (16.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	49.5°F (9.7°C)	Light Rain	Mostly Sunny	Moderately Low	Average
December	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Moderately Low	Average

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

What's included in a St. Michaels vacation package?

A St. Michaels vacation package lets you combine round-trip flights, a hotel stay, and a rental car. St. Michaels vacation packages often feature hotels with easy access to the waterfront, and some properties even offer ocean views. Many hotels in the area provide complimentary breakfast, and while not universally included, some offer airport shuttle service to and from Philadelphia International Airport (PHL).Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a St. Michaels vacation package?

When you bundle, you can save up to 30%*. To save money on a St. Michaels package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

What's the best vacation package for St. Michaels?

For families, a St. Michaels vacation package built around a stay at the 5-star Inn at Perry Cabin (rated 9.3 out of 10) is an excellent choice. This property offers family rooms and an outdoor pool, making it comfortable for all ages, with travelers frequently praising the attentive staff and delicious breakfast.Couples seeking a romantic St. Michaels vacation package might consider the George Brooks House B&B. This charming bed and breakfast, praised by travelers for its excellent staff and clean rooms, offers amenities like free breakfast, free WiFi, and an outdoor pool.Travelers looking for the best value vacation packages in St. Michaels can find comfortable stays at properties like St Michaels Inn. This inn, costing around $150 per night, offers amenities such as free breakfast, free WiFi, and an outdoor pool, and is often noted by travelers for its conveniently located and clean pool.*Package availability and prices may change depending on dates and demand.

Is St. Michaels better suited for a beach vacation or a cultural trip?

St. Michaels is primarily a beach and waterfront destination, known for its outdoor activities and scenic views, making it ideal for a relaxing St. Michaels vacation. Some package hotels offer ocean views, enhancing the coastal experience.However, St. Michaels also boasts a rich history and cultural attractions. You can explore the Chesapeake Bay Maritime Museum, about a 10-minute walk from central St. Michaels, or visit the St. Michaels Winery, about a 5-minute walk away. The town played a significant role in the War of 1812, with historic sites like the Cannonball House and the St. Michaels Historic District reflecting its past. Your St. Michaels vacation package can easily combine both waterfront relaxation and historical exploration.

Is St. Michaels a good choice for a family vacation package?

St. Michaels is a good choice for family vacation packages, offering a blend of outdoor activities and engaging attractions. The destination's family-friendly atmosphere is evident.For accommodations, the 5-star Inn at Perry Cabin, rated 9.3 out of 10 by travelers, is a strong option for families, featuring family rooms and an outdoor pool. For activities, families can enjoy Perry Cabin Park, about a 5-minute walk from central St. Michaels, or explore the interactive exhibits at the Chesapeake Bay Maritime Museum, about a 10-minute walk away. Back Creek Park, also about a 5-minute walk from central St. Michaels, provides another lovely spot for outdoor family time.

What's included in a St. Michaels beach vacation package?

St. Michaels beach vacation packages typically combine flights with a hotel stay, providing a convenient way to experience this charming beach destination. A St. Michaels vacation package could feature a stay at the 5-star Inn at Perry Cabin, rated 9.3 out of 10, which offers an outdoor pool and hot tub, and is highly praised by travelers for its beautiful location and great facilities. Another option is the George Brooks House B&B, which also provides an outdoor pool and is noted for its clean rooms and excellent staff. Specific inclusions like beach access, meals, drinks, or water sports activities depend on the individual hotel and the package rate selected.

What are the top things to do in St. Michaels?

A St. Michaels vacation offers a charming mix of waterfront activities, history, and local flavors:Browse and book things to do in St. Michaels on Expedia.

Do you need to rent a car in St. Michaels, or is public transport enough?

For a St. Michaels vacation package, the town itself is very walkable, making it easy to explore on foot or by bike. However, a rental car offers the most flexibility for exploring the wider region and reaching St. Michaels.Maryland Route 33 is the main road connecting the town to other areas like Tilghman Island and Easton. Since St. Michaels is a beach destination outside a major city, a car is highly recommended for day trips to attractions further afield. While a car isn't strictly needed for resort stays with on-site amenities, it enhances your ability to explore the area during your St. Michaels beach vacation packages.To reach St. Michaels, you'll likely fly into a larger regional airport such as Philadelphia International Airport (PHL), Ronald Reagan Washington National Airport (DCA), Washington Dulles International Airport (IAD), or Baltimore Washington International Thurgood Marshall Airport (BWI). The closest airport is Salisbury - Ocean City Wicomico Regional Airport (SBY). For example, Philadelphia International Airport (PHL) is about 92 miles away, so a car or private transport will be necessary for your journey.

Are St. Michaels vacation package hotels conveniently located?

St. Michaels vacation package hotels are generally very conveniently located, with many properties within easy reach of the town's central area.For example, the 5-star Inn at Perry Cabin, rated 9.3 out of 10, is about a 5-minute walk from central St. Michaels. The Wildset, rated 9.2 out of 10, is also about a 5-minute walk from the center. Even properties slightly further out, like St Michaels Inn, are only about 2 miles from central St. Michaels. This means you can often walk to many attractions, shops, and restaurants, making your St. Michaels vacation package easy to navigate.

Can I change or cancel my St. Michaels vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking St. Michaels vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later St. Michaels vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your St. Michaels vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to St. Michaels?

To find last-minute vacation packages to St. Michaels, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on St. Michaels vacation packages?

Free cancellation on a St. Michaels vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a St. Michaels vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your St. Michaels getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my St. Michaels vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.

St. Michaels Vacations from $674

Book a Hotel + Flight or Car together to unlock savings

Room 1

Your St. Michaels Vacation

The Latest St. Michaels vacation packages

Fenwick Shores, Tapestry Collection by Hilton

Bay Club Resort by Coolvacay

Princess Royale Oceanfront Resort

Bethany Beach Ocean Suites Residence Inn by Marriott

The Shore House

Stay near popular St. Michaels attractions

Chesapeake Bay Maritime Museum

Saint Michaels Village

St. Michaels Winery

1879 Hooper Straight Lighthouse

St Michaels Nature Trail

Perry Cabin Park

St. Michaels Museum

Muskrat Park

What to do in St. Michaels

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

2 Hour Chesapeake Day Sail on Catamaran Epiphany

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

St. Michaels Hotel Deals

St Michaels Inn

Inn at Perry Cabin

The Wildset

Find the Best St. Michaels Vacation Packages

Things to do in and around St. Michaels

Find the best attractions in and around St. Michaels

Best time to go to St. Michaels

Tips to save on your trip to St. Michaels

St. Michaels Essential Information

More vacations you might like

Frequently asked questions

Explore a world of travel with Expedia