Wingate Vacations from $252

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.
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
Price was $264, price is now $252 per person
$252
per person
Mar 12 - Mar 14
just found
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
7.2/10 Good! (415 reviews)
Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish.

Reviewed on Jan 16, 2026

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
Price was $306, price is now $273 per person
$273
per person
Mar 12 - Mar 14
just found
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8/10 Very Good! (75 reviews)
Felt less up to date than pictured

Reviewed on Nov 20, 2025

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
Price was $287, price is now $274 per person
$274
per person
Mar 12 - Mar 14
just found
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8.6/10 Excellent! (847 reviews)
The controls on motorized blinds did not work. No milk for cereal 2 out of 3 days. Very slow to stock breakfast items. There was second TV but remote missing and wifi was si slow we couldn't actually use it. Beds were comfortable and room matched description.

Reviewed on Dec 21, 2025

Don't see what you're looking for?
See all available trips from Columbus to Wingate
View all trips

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 Jan 29 to Jan 30
$240 total
Jan 29 - Jan 30
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Great rooms, amenities, staff

Reviewed on Dec 29, 2025

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 Jan 25 to Jan 26
$79 total
Jan 25 - Jan 26
Total with taxes and fees
6.4/10 (1,001 reviews)
The room was nice

Reviewed on Dec 31, 2025

Days Inn & Suites by Wyndham Cambridge
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 out of 5
2936 Ocean Gtwy Cambridge MD
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $126 total per night from Jan 29 to Jan 30
$126 total
Jan 29 - Jan 30
Total with taxes and fees
8.2/10 Very Good! (800 reviews)
Everything was very nice.

Reviewed on Jan 2, 2026

Comfort Inn & Suites Cambridge
See all 223 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

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 Wingate vacation package cost?
Offering great value package deals from $252 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.

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.