St. Michaels Vacation Packages 2026 from $539

St. Michaels flight + hotel vacation packages

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

The Barefoot Mailman

Midtown Ocean City

$539

per person

Oct 24 - Oct 26

found 20 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Salisbury (SBY)

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool is also provided.

The Shore House

West Ocean City

$1,224

per person

Oct 31 - Nov 2

found 20 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Salisbury (SBY)

This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A seasonal outdoor pool and laundry facilities are also provided.

Miramar Condominiums

Downtown Ocean City

$797

per person

Oct 24 - Oct 26

found 20 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Salisbury (SBY)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.

Ocean 1 Hotel and Suites

Downtown Ocean City

$638

per person

Oct 24 - Oct 26

found 20 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Salisbury (SBY)

Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. Luggage storage is also provided.

Grand Hotel Ocean City Oceanfront

Downtown Ocean City

$570

per person

Oct 24 - Oct 26

found 20 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Salisbury (SBY)

This hotel features 4 restaurants, an outdoor pool, and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free WiFi.

Top St. Michaels hotels deals

St Michaels Inn

1228 S Talbot Street St. Michaels MD

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$105 total

Sep 20 - Sep 21

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

$668 nightly

$735 total

Oct 6 - Oct 7

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

$262 nightly

$288 total

Oct 5 - Oct 6

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

George Brooks House B&B

24500 Rolles Range Road St. Michaels MD

$235 nightly

$259 total

Sep 20 - Sep 21

Total with taxes and fees

This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Enjoy the outdoor pool and conveniences like a terrace and free newspapers.

Pool

Breakfast included

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

Don't see what you're looking for?

See all available properties in St. Michaels

View all properties

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.

See properties

Frequently asked questions

How much are vacation packages to St. Michaels?

$539 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.