Wingate Vacations from $817

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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.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $985, price is now $817 per person
$817
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
9.4/10 Exceptional! (805 reviews)

Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
Price was $1,702, price is now $1,232 per person
$1,232
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
6.6/10 (39 reviews)
the hotel is outdated and needs a complete upgrade, but it was an ok place to sleep and get a shower. it was close to the boardwalk and the office staff was friendly and accommodating. if you are only staying for a day or 2 i would recommend it, the price was reasonable. parking is a little hectic because people cant park right but still an ok place.

Reviewed on Aug 3, 2026

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was $1,021, price is now $831 per person
$831
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
8.8/10 Excellent! (2,551 reviews)
Good locations beautiful views.Indoor pool poor maintenance way too much Clorox!Good food .

Reviewed on Aug 3, 2026

Monte Carlo Boardwalk Oceanfront Ocean City

Monte Carlo Boardwalk Oceanfront Ocean City

3 out of 5
Downtown Ocean City
Price was $1,133, price is now $930 per person
$930
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
8.2/10 Very Good! (1,016 reviews)
I didn’t like the shower head, i didn’t like elevator it was taking forever to come and the AC was right to my head blowing at night!

Reviewed on Aug 4, 2026

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,710, price is now $1,422 per person
$1,422
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Salisbury (SBY)
9.4/10 Exceptional! (24 reviews)
Excellent location. Spacious 2 bedroom condo. FYI.I brought a mattress pad for pull out couch otherwise would not recommend sleeping on it. Double beds were smaller. Hot tub was cold. Kitchen was not stocked with measuring cups or drink pitcher. Only big coffee pot(no keurig).

Reviewed on Jul 31, 2026

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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
$265 nightly
The price is $301 total per night from Aug 31 to Sep 1
$301 total
Aug 31 - Sep 1
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"We had a wonderful stay at the Hyatt Regency Chesapeake Bay Resort. The room was clean, spacious, and very comfortable. The staff was welcoming, attentive, and made us feel at home from check-in to departure. The resort is very family-friendly, with plenty of activities for both kids and adults. ..."

Reviewed on Aug 2, 2026

Hyatt Regency Chesapeake Bay
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
$71 nightly
The price is $79 total per night from Sep 2 to Sep 3
$79 total
Sep 2 - Sep 3
Total with taxes and fees
Days Inn & Suites by Wyndham Cambridge
Cambridge Inn

Cambridge Inn

2 out of 5
2831 Ocean Gateway Cambridge MD
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $83 total per night from Aug 5 to Aug 6
$83 total
Aug 5 - Aug 6
Total with taxes and fees
5.4/10 (595 reviews)
"So let’s start with u get what you pay for I guess. I have stayed a few times thinking different stuff, different room different outcome. Only way I would stay again if they reach out in give me a room couple different reasons. I don’t understand why but even with there WiFi my own personal hotspot ..."

Reviewed on Aug 4, 2026

Cambridge Inn
See all 235 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 $817 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.