Wingate Vacations from $397

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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.
St Michaels Inn

St Michaels Inn

2.5 out of 5
Price was $487, price is now $397 per person
$397
per person
Apr 17 - Apr 20
found 17 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
8.2/10 Very Good! (1,003 reviews)
Room was fine. Breakfast was poor with two empty hot breakfast servers. Rest of food substandard. Staff was nice

Reviewed on Jan 18, 2026

Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
Downtown St. Michaels
Save 100% on your flight
Price was $965, price is now $668 per person
$668
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.6/10 Exceptional! (369 reviews)
Friendly and attentive staff, good cleaning services

Reviewed on Oct 26, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $2,121, price is now $1,637 per person
$1,637
per person
Apr 7 - Apr 10
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
7.6/10 Good! (95 reviews)
Everything was exactly what you would expect for a budget friendly room, only complaint was that the steps and porch going to 3rd floor was sketchy and theres a large soft spot on 3rd floor side landing

Reviewed on Oct 17, 2025

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,318, price is now $1,076 per person
$1,076
per person
May 5 - May 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
9.4/10 Exceptional! (15 reviews)
Stayed in unit 505 and it was beautiful! We loved it!

Reviewed on Aug 23, 2025

Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
Price was $822, price is now $683 per person
$683
per person
May 5 - May 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
6/10 (681 reviews)
Very helpful staff and clean property

Reviewed on Dec 2, 2025

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Wingate 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
$211 nightly
The price is $240 total per night from Mar 3 to Mar 4
$240 total
Mar 3 - Mar 4
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
The staff was very nice and helpful. The room was clean but cold. Even though we had the thermostat set to 74, it was still cold. All the amenities were great. It would have been nice if the room beds had been made and if fresh towels had been left in the room. Housekeeping didn't show up until 5:30 ...

Reviewed on Feb 22, 2026

Hyatt Regency Chesapeake Bay
Comfort Inn & Suites Lexington Park near Pax River

Comfort Inn & Suites Lexington Park near Pax River

2.5 out of 5
21885 Three Notch Rd Lexington Park MD
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $125 total per night from Mar 1 to Mar 2
$125 total
Mar 1 - Mar 2
Total with taxes and fees
8.6/10 Excellent! (670 reviews)
Hotel had been nicely updated. Great room and very clean.

Reviewed on Feb 22, 2026

Comfort Inn & Suites Lexington Park near Pax River
Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

2.5 out of 5
2917 Ocean Gateway Cambridge MD
Fully refundableReserve now, pay when you stay
$64 nightly
The price is $71 total per night from Feb 26 to Feb 27
$71 total
Feb 26 - Feb 27
Total with taxes and fees
6.6/10 (1,002 reviews)
Very comfortable and quiet

Reviewed on Feb 14, 2026

Days Inn & Suites by Wyndham Cambridge
See all 220 properties in Wingate
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 $397 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.