St. Michaels Vacation Packages

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Your St. Michaels Vacation

The fascinating city of St. Michaels is calling your name. Immerse yourself in everything it has to offer with a St. Michaels vacation package that's tailored to you. You'll want to take in some sights during your trip to St. Michaels. Drop by major attractions such as St. Michaels Winery, Chesapeake Bay Maritime Museum and St. Michaels Museum. Stop daydreaming and start doing. Browse the many options on Expedia today and finally put your St. Michaels vacation plans in motion!

Top St. Michaels Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

2.5 out of 5
Midtown Ocean City
Price was CA $1,832, price is now CA $1,690 per person
CA $1,690
per person
Oct 2 - Oct 6
found 9 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
8/10 Very Good! (1,002 reviews)
Didn’t like that I had to pay another $20 for a resort fee and parking pass. The restaurant- pub was closed. The pool closed at 8pm. The room was tiny and no balcony.

Reviewed on Aug. 24, 2025

Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was CA $3,859, price is now CA $3,362 per person
CA $3,362
per person
Oct 2 - Oct 6
found 9 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
8.2/10 Very Good! (650 reviews)
Parking wasn’t the greatest as it took second day to finally have them put the extra flow parking in our gps cause we couldn’t find it,at hotel it’s only maybe 15 spots to park,when we walked in our room smelt weird like mildew stinky wet mop but there was still so much sand and stuff on floor like wasn’t swept even the bathroom floor so that’s was weird to smell that and we smelt throw up smell on our 4th floor few times,but our neighbors smoking weed anytime our door was open on deck few times we smelt it bad even with door shut and coming back from wherever we where our room did,staff was all very nice and soon asked for towels we got within a reasonable time too

Reviewed on Aug. 18, 2025

OCHG Bel Harbour Unit 1

OCHG Bel Harbour Unit 1

2 out of 5
Downtown Ocean City
Price was CA $3,002, price is now CA $2,664 per person
CA $2,664
per person
Oct 2 - Oct 6
found 9 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
No reviews
Harrison Hall Hotel

Harrison Hall Hotel

2 out of 5
Downtown Ocean City
Price was CA $2,178, price is now CA $1,985 per person
CA $1,985
per person
Oct 2 - Oct 6
found 9 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
7.6/10 Good! (1,018 reviews)
The room carpet needs to be clean it has a smell of feet

Reviewed on Aug. 26, 2025

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was CA $2,164, price is now CA $1,987 per person
CA $1,987
per person
Oct 2 - Oct 6
found 9 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Salisbury (SBY)
8.6/10 Excellent! (2,022 reviews)
Very clean and updated rooms.

Reviewed on Aug. 26, 2025

Ready to book your vacation to St. Michaels?

 

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St. Michaels Hotel Deals

St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
The price is CA $131 per night from Sep 1 to Sep 2
CA $131
CA $145 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very Good! (1,006 reviews)
"Great place to stay"

Reviewed on Aug. 23, 2025

St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is CA $792 per night from Sep 17 to Sep 18
CA $792
CA $958 total
Sep 17 - Sep 18
includes taxes & fees
9.4/10 Exceptional! (361 reviews)
Lived up to its Reputation
"My wife and I recently stayed here to celebrate a milestone birthday. It certainly lived up to the hype and was one do the nicer places we have ever stayed."

Reviewed on Aug. 25, 2025

Inn at Perry Cabin
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St, St. Michaels, MD
The price is CA $331 per night from Sep 9 to Sep 10
CA $331
CA $394 total
Sep 9 - Sep 10
includes taxes & fees
9.6/10 Exceptional! (361 reviews)
"Our room was lovely and exactly as described online. Loved the complementary snacks. Breakfast was delicious. We were particularly impressed with the guest services. Everyone was gracious, helpful, and welcoming. Dining at Ruse is a must!! Make reservations in advance. The food and service are ..."

Reviewed on Aug. 15, 2025

The Wildset
See all 1,292 properties in St. Michaels
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.
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Frequently asked questions

How much does a St. Michaels vacation package cost?
You'll find cheap prices from CA $1,690 on Expedia for your St. Michaels break. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to St. Michaels costs.
What are the cheapest months to go to St. Michaels?
If you're looking to snag a cheap St. Michaels vacation package, consider planning a trip in January, February and March. You'll usually find lower rates on flights and hotels during these months — perfect for budget-conscious travellers.
How many days is enough for St. Michaels?
Usually, a handful of days is enough to go to the main attractions during your St. Michaels vacation. However, if you prefer to have more time to relax or go on day trips, consider extending your itinerary.
Is it worth booking a vacation package to St. Michaels?
Well known for its watersports, culture and nature, a St. Michaels vacation offers something for everyone. Be sure to visit major sights like Chesapeake Bay Maritime Museum and St. Michaels Museum, and consider renting some wheels for day trips to discover even more.
How to find the best St. Michaels package deals?
Bagging a cheap St. Michaels package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable St. Michaels package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a St. Michaels vacation as a package?
You can enjoy significant savings on your next St. Michaels break by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to St. Michaels?
If you've got your St. Michaels vacation dates confirmed, book as soon as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to St. Michaels?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to St. Michaels.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and meals to experiences and flights. Your accommodations will likely be the biggest expense during your trip to St. Michaels.
  3. Decide how long to go for: Now that you're up to speed on St. Michaels, you can figure out the perfect length of your vacation. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored St. Michaels vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.