St. Michaels Vacation Packages 2026 from $301

St. Michaels flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Gold Leaf Hotel of Dewey - Rehoboth Beach

$301

per person

Nov 26 - Dec 1

found 2 hours ago

Roundtrip flight included

Chicago (ORD) to Salisbury (SBY)

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Free self parking, laundry facilities, and free newspapers are also on offer.

Fenwick Shores, Tapestry Collection by Hilton

Save 100% on your flight

$385

per person

Nov 26 - Dec 1

found 2 hours ago

Roundtrip flight included

Chicago (ORD) to Salisbury (SBY)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Bethany Beach Ocean Suites Residence Inn by Marriott

Downtown Bethany Beach

Save 100% on your flight

$536

per person

Nov 26 - Dec 1

found 2 hours ago

Roundtrip flight included

Chicago (ORD) to Salisbury (SBY)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.

Beach House Dewey

Save 100% on your flight

$1,058

per person

Nov 26 - Dec 1

found 2 hours ago

Roundtrip flight included

Chicago (ORD) to Salisbury (SBY)

This hotel features a 24-hour gym and a seasonal outdoor pool. Enjoy the a rooftop terrace and perks like free WiFi. Self parking, a coffee shop, and a grocery/convenience store are also offered.

Hotel Bethany Beach

$532

per person

Nov 26 - Dec 1

found 2 hours ago

Roundtrip flight included

Chicago (ORD) to Salisbury (SBY)

This hotel features an outdoor pool and a gym. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. Self parking, a business center, and a snack bar/deli are also offered.

Top St. Michaels hotels deals

St Michaels Inn

1228 S Talbot Street St. Michaels MD

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$88 total

Nov 26 - Nov 27

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the conference center and conference space on site. Enjoy the seasonal outdoor pool and conveniences like a terrace and laundry facilities.

Pool

Breakfast included

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

$485 nightly

$533 total

Nov 11 - Nov 12

Total with taxes and fees

This luxury hotel features a golf course, a full-service spa, and a marina. Families will appreciate complimentary bicycles, kid-friendly dining, and in-room childcare. Enjoy the 3 outdoor tennis courts and perks like free valet parking and free WiFi.

Pool

Hot Tub

The Wildset

209 N Talbot St St. Michaels MD

Free Cancellation

Reserve now, pay when you stay

$252 nightly

$277 total

Nov 9 - Nov 10

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A coffee shop, a snack bar/deli, and concierge services are also on offer.

Breakfast included

Pet friendly

Parsonage Inn

210 North Talbot Street St. Michaels MD

$250 nightly

$275 total

Nov 2 - Nov 3

Total with taxes and fees

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A terrace, a garden, and a lobby fireplace are also on offer.

Breakfast included

Pet friendly

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD

Get rates

This cottage features a garden, laundry facilities, and barbecue grills.

Pool

Kitchen

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels MD

Get rates

This cottage features a garden, laundry facilities, and barbecue grills.

Pool

Kitchen

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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.

Chesapeake Bay Maritime Museum

9.4/10 (91 reviews)

You can study the exhibits at Chesapeake Bay Maritime Museum, a museum with a storied past, during your trip to St. Michaels. Stroll along the waterfront or experience the area's museums.

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Frequently asked questions

How much are vacation packages to St. Michaels?

$301 is all you need to spend for an exhilarating escape in St. Michaels. Bundle your flights and hotel into a Travelocity package and watch the savings pile up. With prices this good, you'll want to start packing your suitcase now!

How long should my St. Michaels vacation be?

If you need some guidance, most visitors spend an average of 2 nights vacationing in St. Michaels. But to discover the true essence of this place, stay a bit longer. That way you can tick off more attractions and really take in the local vibe.

Where can I get the best vacation package deals for St. Michaels?

With at least 400 airlines and 1,000,000 hotels around the world, it's hard to top Travelocity. Take advantage of our impressive range and score an incredible St. Michaels package deal. Isn't it great when travel is that easy?

Why should I purchase my St. Michaels vacation package via Travelocity?

From our 24/7 customer support to our range of fantastic destinations, we're committed to giving you the most unforgettable escape. All you'll have to do is click and book — our Price Match Guarantee will make sure you score the best deal.

Can I save on my St. Michaels car rental if I bundle it with a hotel or flight?

Combining your hotel, car and flight into a St. Michaels vacation package is the easiest way to land the best prices. Plus, having your own wheels gives you total freedom to get to all those big-name sights you're itching to see. Sitting 45 mi away from St. Michaels, White House is one attraction that should have a place on your itinerary. Load up the car and make a day trip of it.

What is the best time of year to go to St. Michaels?

March, July and October is peak season here, while January, September and December usually experience less crowds. If your bank balance is your first consideration, try to avoid visiting in as it's usually the dearest time. The least expensive month to explore this part of the world is .

Which airport is best for St. Michaels?

Ronald Reagan Washington National Airport (DCA) is a main hub. It's situated approximately 45 mi west of St. Michaels. Other options worth checking out are Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (35 mi away from central St. Michaels) and Salisbury - Ocean City Wicomico Regional Airport (SBY) (50 mi away from central St. Michaels).

What is there to do in St. Michaels?

St. Michaels is full of places to explore, like St. Michaels Winery and Chesapeake Bay Maritime Museum. These two impressive attractions are at the top of most tourists' travel itineraries.

Where should I stay when visiting St. Michaels?

The St Michaels Inn is popular with many travelers. Book as soon as possible before it's too late.