Secretary Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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!

Secretary Hotel Deals

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $211 total per night from Nov 23 to Nov 24
$211 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,012 reviews)
Pleasant staff, clean accommodations although could benefit from a modern upgrade. Restaurant was knowledgeable and helpful in assisting my wife with accommodating celiac options.

Reviewed on Oct 26, 2025

Hyatt Regency Chesapeake Bay
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
$100 nightly
The price is $111 total per night from Nov 6 to Nov 7
$111 total
Nov 6 - Nov 7
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
Basic room, clean and comfortable. Only complaint, it took 15 minutes to get hot water in the shower -- wasted a lot of water waiting. Good TV selection, too.

Reviewed on Oct 17, 2025

St Michaels Inn
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

2.5 out of 5
8708 Alicia Drive, Easton, MD
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $131 total per night from Nov 9 to Nov 10
$131 total
Nov 9 - Nov 10
Total with taxes and fees
9.2/10 Wonderful! (1,008 reviews)
The young lady at the front desk that was there last night and again first thing this morning was wonderful

Reviewed on Oct 26, 2025

Best Western Plus Easton Inn & Suites
See all 257 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.

Find the Best Secretary Vacation Packages

Secretary Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Salisbury - Ocean City Wicomico Regional Airport (SBY)
Population
530
Top Sights
Bill Burton Fishing Pier State Park, Laytons Chance Vineyard and Winery and Choptank River Lighthouse

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Secretary vacation package cost?
You'll find cheap prices on Expedia for your Secretary break. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Secretary costs.
What are the cheapest months to go to Secretary?
November, December and January are the best times to search for cheap Secretary vacation packages. Choosing to travel in less busy periods means you can typically find lower prices on flights and hotels.
How many days is enough for Secretary?
The ideal duration of your Secretary vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you enough time to visit all the major attractions and discover some hidden spots along the way.
How to find the best Secretary package deals?
Start your search for a Secretary package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Secretary package deal straight away, simply play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Secretary adventure underway.
Is it cheaper to book a Secretary vacation as a package?
You can enjoy significant savings on your Secretary getaway by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to view some great flight and hotel 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 Secretary?
If you have your Secretary vacation dates confirmed, book as early as you can to score some fantastic deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Secretary vacation packages?
Your Secretary getaway should be a relaxing escape from your daily routine, not a source of money worries. So to give you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

Explore a world of travel with Expedia

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