St. Michaels Vacation Packages 2025/2026 from $675

St. Michaels flight + hotel vacation packages

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

Boardwalk One

Downtown Ocean City

$675

per person

Dec 7 - Dec 10

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Salisbury (SBY)

This aparthotel features a seasonal outdoor pool and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. Dry cleaning and laundry facilities are also provided.

Club Ocean Villas II

North Ocean City

$813

per person

Dec 7 - Dec 10

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Salisbury (SBY)

A marina and an indoor pool are featured at this smoke-free apartment. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like a picnic area and a virtual front desk.

Beach Walk

Downtown Ocean City

$2,065

per person

Dec 7 - Dec 10

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Salisbury (SBY)

This hotel features free self parking and express check-in. Express check-out is also provided.

Grand Hotel Ocean City Oceanfront

Downtown Ocean City

$677

per person

Dec 7 - Dec 10

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) 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 self parking and free WiFi.

Motel 6 Salisbury, MD

$720

per person

Dec 7 - Dec 10

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Salisbury (SBY)

Free self parking is available and the motel's front desk is staffed around-the-clock. WiFi in public areas is free. A snack bar/deli is also provided.

Top St. Michaels hotels deals

St Michaels Inn

1228 S Talbot Street, St. Michaels, MD

$100 nightly

$111 total

Nov 6 - Nov 7

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

$425 nightly

$467 total

Nov 17 - Nov 18

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

$249 nightly

$274 total

Nov 6 - Nov 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

George Brooks House B&B

24500 Rolles Range Road, St. Michaels, MD

$200 nightly

$220 total

Nov 5 - Nov 6

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!

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

Pool

Kitchen

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

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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

4.5/5(15 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.

St. Michaels Winery

4.5/5(45 reviews)

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?

$675 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.