St. Michaels Vacation Packages 2025/2026 from $123

St. Michaels flight + hotel vacation packages

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

The Americana Hotel

Downtown Ocean City

$123

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Salisbury (SBY)

This hotel features a restaurant and 2 bars/lounges. Enjoy the indoor pool and perks like free WiFi. Self parking and a safe deposit box are also offered on site.

Comfort Suites Ocean City West

West Ocean City

$160

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Salisbury (SBY)

This hotel features a gym and a seasonal outdoor pool. Bring the family and enjoy the waterslide, playground, and arcade/game room. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking.

Holiday Inn & Suites Ocean City by IHG

Downtown Ocean City

$197

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Salisbury (SBY)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the hot tub, poolside bar, and laundry facilities.

Home2 Suites by Hilton Ocean City - Bayside, MD

North Ocean City

$144

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Salisbury (SBY)

This hotel doesn't skimp on freebies - guests receive free breakfast and free WiFi. Business travelers can take advantage of the 24-hour business center. There's an indoor pool on site, and laundry facilities and barbecue grills are also offered.

Hyatt Place Ocean City / Oceanfront

Downtown Ocean City

$164

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Salisbury (SBY)

This hotel features a bar/lounge, a poolside bar, and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.

Top St. Michaels hotels deals

St Michaels Inn

1228 S Talbot Street, St. Michaels, MD

Free Cancellation

$92 nightly

$102 total

Oct 7 - Oct 8

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

The Wildset

209 N Talbot St, St. Michaels, MD

Free Cancellation

Reserve now, pay when you stay

$239 nightly

$263 total

Oct 6 - Oct 7

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

Inn at Perry Cabin

308 Watkins Ln, St. Michaels, MD

$589 nightly

$648 total

Oct 22 - Oct 23

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

George Brooks House B&B

24500 Rolles Range Road, St. Michaels, MD

$207 nightly

$228 total

Oct 1 - Oct 2

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

Parsonage Inn

210 North Talbot Street, St. Michaels, MD

$229 nightly

$252 total

Oct 1 - Oct 2

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!

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.

Popular places to visit

Chesapeake Bay Maritime Museum

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.

St. Michaels Winery

You can enjoy a tasting or tour at St. Michaels Winery during your travels to St. Michaels. Discover the seafood restaurants and its museums while you're in the area.

St. Michaels Marina

Explore the waterfront in St. Michaels with a trip to St. Michaels Marina. Stroll along the waterfront or visit the shops in this romantic area.

Frequently asked questions

How much are vacation packages to St. Michaels?

$123 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.