Midway Vacations from $317

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Your Midway Vacation

From its highlights to its hidden gems, this city is best experienced with a Midway vacation package. Find a place to stay in Winston-Salem, which is good for nature, culture and history. Eager to do a little sightseeing? Spend your days exploring leading attractions like Olde Homeplace Golf Club during your trip to Midway. Stop daydreaming and start doing. Explore the wide range of options on Expedia today and finally put your Midway vacation plans in motion!

The Latest Midway vacation packages

Price found within the past 48 hours. Click for updated prices.
Four Points by Sheraton Greensboro Airport

Four Points by Sheraton Greensboro Airport

3 out of 5
Price was $385, price is now $317 per person
$317
per person
Jan 21 - Jan 25
found 21 hours ago
Roundtrip flight included
Miami (MIA) to Greensboro (GSO)
8.4/10 Very Good! (1,022 reviews)
Room was not fancy but clean. Good quiet hotel felt safe there as a female traveling alone. Would stay there again!

Reviewed on Nov 12, 2025

Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was $2,248, price is now $499 per person
$499
per person
Jan 16 - Jan 20
found 5 hours ago
Roundtrip flight included
Miami (MIA) to Greensboro (GSO)
10/10 Exceptional! (107 reviews)
The home was beautiful and felt very welcoming.

Reviewed on Nov 12, 2025

O.Henry Hotel

O.Henry Hotel

4 out of 5
Save 100% on your flight
Price was $899, price is now $629 per person
$629
per person
Jan 16 - Jan 20
found 5 hours ago
Roundtrip flight included
Miami (MIA) to Greensboro (GSO)
9.8/10 Exceptional! (712 reviews)
Clean old world room with comfortable mattress and pillows great Room with luxe products

Reviewed on Nov 6, 2025

Hotel Denim

Hotel Denim

3.5 out of 5
Price was $524, price is now $397 per person
$397
per person
Jan 21 - Jan 25
found 21 hours ago
Roundtrip flight included
Miami (MIA) to Greensboro (GSO)
9/10 Wonderful! (1,013 reviews)
I love the vibe at this hotel. Beautifully appointed with a hip, boutiquee feel. Made to order breakfast exceptional. Free alcohol drink with your stay and Happy Hour every night. Location is unbeatable. King bed and bed linens very high quality. Highly recommend.

Reviewed on Nov 10, 2025

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $896, price is now $705 per person
$705
per person
Jan 16 - Jan 20
found 5 hours ago
Roundtrip flight included
Miami (MIA) to Greensboro (GSO)
9.6/10 Exceptional! (869 reviews)
Great stay at The Proximity! Bed was cozy, room was wonderful and the hotel overall had a great vibe. Will definitely be back!

Reviewed on Nov 7, 2025

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Discover the most popular places to visit in Midway

First Methodist Church

Old Salem

4.5/5(264 reviews)

You can spend time exploring the galleries in Old Salem during your trip to Winston-Salem. Amble around this family-friendly area's lush forest or attend a sporting event.

Old Salem
Awesome racing!

Bowman Gray Stadium

4/5(5 reviews)

Catch an event at Bowman Gray Stadium during your trip to Winston-Salem. Amble around this family-friendly area's lush forest or attend a sporting event.

Bowman Gray Stadium
Tropical in the greenhouse

Reynolda Gardens

5/5(43 reviews)

Reynolda Gardens is just one of the places to see in Winston-Salem, so why not enjoy the other things to explore during your travels? Amble around the area's lush forest or attend a sporting event.

Reynolda Gardens

What to do in Midway

Winston-Salem True Crime Tour

Winston-Salem True Crime Tour

$19
per adult
Winston-Salem True Crime Tour
Lantern Light and Spooky Stories

Carolina History & Haunts Winston-Salem Historical Ghost Tour

$26
per adult
100% of travellers recommend
Carolina History & Haunts Winston-Salem Historical Ghost Tour
See all activities in Midway

Midway Hotel Deals

DoubleTree by Hilton Greensboro Airport

DoubleTree by Hilton Greensboro Airport

4 out of 5
6426 Burnt Poplar Road, Greensboro, NC
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $92 total per night from Nov 23 to Nov 24
$92 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (803 reviews)
All good Cold water in BR doesn't work.

Reviewed on Nov 8, 2025

DoubleTree by Hilton Greensboro Airport
Four Points by Sheraton Greensboro Airport

Four Points by Sheraton Greensboro Airport

3 out of 5
7619 Thorndike Rd, Greensboro, NC
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $89 total per night from Nov 16 to Nov 17
$89 total
Nov 16 - Nov 17
Total with taxes and fees
8.2/10 Very Good! (1,014 reviews)
Room was not fancy but clean. Good quiet hotel felt safe there as a female traveling alone. Would stay there again!

Reviewed on Nov 12, 2025

Four Points by Sheraton Greensboro Airport
Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
420 High St, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
$64 nightly
The price is $72 total per night from Nov 30 to Dec 1
$72 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
Room was clean with needed amenities.

Reviewed on Nov 8, 2025

Hawthorne Inn and Conference Center
See all 970 properties in Midway
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 Midway Vacation Packages

Midway Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Piedmont Triad Intl. Airport (GSO)
Population
4,700
Top Sights
Reynolda House Museum of American Art, Southeastern Center for Contemporary Art and Theatre Alliance

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Frequently asked questions

How much does a Midway vacation package cost?
You can snap up a vacation package to this popular destination from $317 on Expedia. However, how much your vacation to Midway costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Midway?
If you'd like to score a cheap Midway vacation package, consider traveling in September, November and December. You'll generally find better prices on hotels and airfares during these months — ideal for a budget-friendly break.
How many days is enough for Midway?
Typically, a handful of days is enough to explore the top attractions during your Midway vacation. But if you'd like to have some time to relax or go on day trips, consider extending your trip.
How to find the best Midway package deals?
Use Expedia's filters to help you find some fabulous Midway package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or browse for Midway package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Midway vacation as a package?
You can enjoy significant savings on your next Midway retreat by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to view some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Midway?
Secure incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Midway adventure.
Does Expedia offer Book Now, Pay Later Midway vacation packages?
If you're like us, you love traveling the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Midway vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.