Secretary Vacation Packages

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Your Secretary Vacation

There's no better way to embark on an adventure than with one of our vacation packages to Secretary. The rich history and spectacular views are just two of the many reasons you'll want to stay in this fascinating city. During your trip to Secretary, take all the time you need for sightseeing. A perfect place to start is Bill Burton Fishing Pier State Park. Stop dreaming and start traveling. Check out the broad range of options on Expedia today and put your Secretary vacation plans into action!

Top Secretary Vacation Deals

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

St Michaels Inn

2.5 out of 5
Price was CA $742, price is now CA $675 per person
CA $675
per person
Oct 16 - Oct 19
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Salisbury (SBY)
8.2/10 Very good! (1,013 reviews)
Hotel and our rooms were clean, and the price was right. The hotel clearly had it's hey-day several decades ago. Our rooms were damp - very hard to get towels to dry while there, and most things felt damp when we got home to unpack. The weekday continental breakfast was missing bowls, milk, and butter for an already-limited spread. The staff were very polite but did not do anything to amend the breakfast situation when advised. We got what we paid for, and would not return.

Reviewed on Aug 5, 2026

Downtown Flat Walk to Dining Shops Sleeps 4

Downtown Flat Walk to Dining Shops Sleeps 4

2 out of 5
Downtown St. Michaels
Price was CA $1,316, price is now CA $1,171 per person
CA $1,171
per person
Oct 16 - Oct 18
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Salisbury (SBY)
No reviews

Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
Downtown St. Michaels
Price was CA $3,346, price is now CA $3,082 per person
CA $3,082
per person
Oct 16 - Oct 19
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Salisbury (SBY)
9.6/10 Exceptional! (395 reviews)

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3 out of 5
Price was CA $1,374, price is now CA $1,321 per person
CA $1,321
per person
Oct 16 - Oct 19
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Salisbury (SBY)
9/10 Wonderful! (1,007 reviews)

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 out of 5
Price was CA $1,076, price is now CA $1,053 per person
CA $1,053
per person
Oct 16 - Oct 18
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Salisbury (SBY)
9.2/10 Wonderful! (1,009 reviews)
Staff was wonderful and friendly, and our room was impeccably clean. Breakfast was simple but had the essentials!

Reviewed on Aug 5, 2026

Ready to book your vacation to Secretary?

 

Choose your dates

Secretary Hotel Deals

St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Aug 26 to Aug 27
CA $119
CA $130 total
Aug 26 - Aug 27
includes taxes & fees
8.2/10 Very good! (1,002 reviews)
"Hotel and our rooms were clean, and the price was right. The hotel clearly had it's hey-day several decades ago. Our rooms were damp - very hard to get towels to dry while there, and most things felt damp when we got home to unpack. The weekday continental breakfast was missing bowls, milk, and butter ..."

Reviewed on Aug 5, 2026

St Michaels Inn
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
The price is CA $309 per night from Aug 24 to Aug 25
CA $309
CA $418 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"I love everything, the fishing area was amazing, my kids loved it."

Reviewed on Aug 4, 2026

Hyatt Regency Chesapeake Bay
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Aug 9 to Aug 10
CA $233
CA $257 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (904 reviews)
"The location was great and property was very well kept and accommodating. Staff was very friendly and helpful. Had a great dinner at restaurant on property. Room was comfortable but bathroom very tight with no counter space for use of toiletries. I know it is a historic property with limited space ..."

Reviewed on Jul 29, 2026

The Tidewater Inn
See all 267 properties in Secretary
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Frequently asked questions

How much does a Secretary vacation package cost?
You'll find cheap prices from CA $675 on Expedia for your Secretary getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Secretary costs.
What are the cheapest months to go to Secretary?
You can usually find lower prices and better availability in January, February and November. Take a look at our cheap Secretary vacation packages and you could land some great off-season deals.
How many days is enough for Secretary?
The ideal duration of your Secretary vacation depends on what you'd like to see. Usually, a few days to a week will give you enough time to hit all the top attractions and explore some hidden gems along the way.
How to find the best Secretary package deals?
Finding a cheap Secretary package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Secretary 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 often lower.
Is it cheaper to book a Secretary vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations and flights individually. Better still, you can personalize your Secretary trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Secretary?
If you're considering a spontaneous Secretary vacation, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Secretary?

  1. Choose when to travel: Check your diary and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to vacation in Secretary.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and airfares. Your hotel will probably be the largest expense during your trip to Secretary.
  3. Decide how many days away: Start by making a list of all the activities and attractions you'd like to experience in Secretary. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Secretary vacation package that brings all your bookings together.

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