St. Michaels Vacation Packages 2025/2026 from $350

St. Michaels flight + hotel vacation packages

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

Microtel Inn & Suites by Wyndham Milford

per person

Sep 18 - Sep 21

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Salisbury (SBY)

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Bethany Beach Ocean Suites Residence Inn by Marriott

Save 100% on your flight

per person

Sep 18 - Sep 21

found 9 hours ago

Roundtrip flight included

Boston (BOS) 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 Walk

Downtown Ocean City

Save 100% on your flight

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Salisbury (SBY)

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

Sahara Motel

Downtown Ocean City

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Salisbury (SBY)

A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.

White Marlin Inn

Downtown Ocean City

per person

Sep 25 - Sep 29

found 7 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Salisbury (SBY)

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

Top St. Michaels hotels deals

Inn at Perry Cabin

308 Watkins Ln, St. Michaels, MD

$629 nightly

$692 total

Sep 1 - Sep 2

Total includes 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.

The Wildset

209 N Talbot St, St. Michaels, MD

Free Cancellation

Reserve now, pay when you stay

$217 nightly

$239 total

Aug 19 - Aug 20

Total includes 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.

St Michaels Inn

1228 S Talbot Street, St. Michaels, MD

Free Cancellation

$95 nightly

$105 total

Sep 2 - Sep 3

Total includes 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.

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Get rates

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

Pool

Kitchen

Parsonage Inn

210 North Talbot Street, St. Michaels, MD

$229 nightly

$252 total

Aug 4 - Aug 5

Total includes 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

Historic Inns of Annapolis

58 State Circle, Annapolis, MD

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$163 total

Aug 10 - Aug 11

Total includes taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A terrace, limo/town car service, and a garden are also on offer.

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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?

$350 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.