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.
Rodeway Inn

Rodeway Inn

2 out of 5
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Salisbury (SBY)
7/10 Good! (330 reviews)
First room had water on the bathroom floor, second room attempt was unprepared ...Beds were not made. Third room was fine and clean. Breakfast was minimal and neglected by staff... No plates, no napkins until requested

Reviewed on Aug. 1, 2025

Microtel Inn & Suites by Wyndham Milford

Microtel Inn & Suites by Wyndham Milford

2.5 out of 5
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Salisbury (SBY)
8.8/10 Excellent! (579 reviews)
Every thing was great. The lady at front desk was so nice and friendly.

Reviewed on Aug. 3, 2025

Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Salisbury (SBY)
8.6/10 Excellent! (1,012 reviews)
The best part of this hotel was its closeness to the beach. I think the property itself is a little run down by age. A new carpet would have made a difference, but overall it was a clean comfortable stay. The staff was very nice.

Reviewed on Aug. 3, 2025

Comfort Inn & Suites Milford

Comfort Inn & Suites Milford

2.5 out of 5
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Salisbury (SBY)
8/10 Very Good! (575 reviews)
If details matter, you won’t like this hotel. My sink faucet was leaking. My tub faucet was dripping. Tub base was stained. Otherwise my stay was fine. Nice people at the desk.

Reviewed on Jul. 9, 2025

The Bay Resort

The Bay Resort

2.5 out of 5
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Salisbury (SBY)
8.6/10 Excellent! (761 reviews)
Our favorite thing about the hotel was the view from our balcony. It was so peaceful and it was the perfect place to watch the sunset over the bay. The location was perfect - once you parked, there was no need to use your car again. The Ocean was 2 short blocks away and there was a great assortment of restaurants in walking distance. Some of the faciliy is a bit dated, but it was clean and the staff was super nice and helpful. We will be returning!

Reviewed on Jul. 28, 2025

Ready to book your vacation to St. Michaels?

 

Choose your dates

St. Michaels Hotel Deals

Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is CA $813 per night from Sep 1 to Sep 2
CA $813
CA $983 total
Sep 1 - Sep 2
includes taxes & fees
9.4/10 Exceptional! (355 reviews)
"The setting is spectacular and the staff could not have been kinder and more helpful."

Reviewed on Jul. 13, 2025

Inn at Perry Cabin
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St, St. Michaels, MD
Fully refundableReserve now, pay when you stay
The price is CA $272 per night from Aug 19 to Aug 20
CA $272
CA $329 total
Aug 19 - Aug 20
includes taxes & fees
9.6/10 Exceptional! (346 reviews)
"Site was exactly as advertised. The team was very responsive, and the service at breakfast wonderful. My only complaint would be the excessive (in my opinion) property lighting all through the night."

Reviewed on Jul. 31, 2025

The Wildset
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is CA $133 per night from Sep 2 to Sep 3
CA $133
CA $147 total
Sep 2 - Sep 3
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"We had a great time during our visit. Pool could use more seating and umbrellas. Rooms a bit dated. Overall, great time and would return. Great value for your money"

Reviewed on Jul. 31, 2025

St Michaels Inn
See all 1,285 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 $511 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.