Wingate Vacations from $1,412
Book a Hotel + Flight or Car together to unlock savings
Your Wingate Vacation
Our vacation packages to Wingate provide endless opportunities to indulge in new sights, sounds and sensations. And with all the travel planning taken care of, you'll be free to enjoy your city adventure without a worry in the world. Fill your schedule with tours of Middle Hooper Island, Lower Hooper Island and Elliott Island, some of the things you simply have to see during a trip to Wingate. Whoever you're taking time off with and whatever your budget, your dream Wingate vacation is just a few clicks away with Expedia.
The Latest Wingate vacation packages
Price found within the past 48 hours. Click for updated prices.
Inn at Perry Cabin
Downtown St. Michaels
$1,784
per person
Nov 26 - Nov 29
found 3 hours ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
9.6/10 Exceptional! (399 reviews)
It’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way.
Reviewed on Sep 8, 2026
Wingate Hotel Deals
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
$260 nightly
$295 total
Oct 13 - Oct 14
Total with taxes and fees
Days Inn & Suites by Wyndham Cambridge
2917 Ocean Gateway Cambridge MD
Fully refundableReserve now, pay when you stay
$64 nightly
$71 total
Sep 21 - Sep 22
Total with taxes and fees
Comfort Inn & Suites Cambridge
2936 Ocean Gtwy Cambridge MD
Fully refundable
$118 nightly
$131 total
Oct 11 - Oct 12
Total with taxes and fees
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 Wingate Vacation Packages
Wingate Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Max Temp Winter | 45ºF |
Max Temp Summer | 80ºF |
Top Sights | Cedar Hill Marina, Shark Fin Shoal and Harriet Tubman Underground Railroad National Historical Park |
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Frequently asked questions
How much does a Wingate vacation package cost?
Offering great value package deals from $1,412 on Expedia, you'll be pleasantly surprised at how much a vacation to Wingate costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Wingate?
You can generally find reduced prices and greater availability in November, December and January. Check out our cheap Wingate vacation packages and you could get some excellent off-season deals.
How many days is enough for Wingate?
The ideal duration for your Wingate vacation depends on what you'd like to see. Typically, a few days to a week will give you plenty of time to tick off all the main attractions and discover some hidden spots along the way.
How to find the best Wingate package deals?
Finding a cheap Wingate package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most affordable Wingate package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Wingate vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations separately. Better still, you can personalize your Wingate escape to fit your exact style. Choose 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 Wingate?
If you're planning a spontaneous Wingate trip, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Wingate vacation packages?
Your Wingate break should be a relaxing escape from your daily routine, not a source of money worries. So to give you extra flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
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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.