Midway Vacations from $525

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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.
  • A multi-story building with a sign reading 'STUDIOS'.
    Jan 13 - Jan 18

    StudioRes by Marriott Greensboro Airport + Flight

    Greensboro
    5 nights
    3.0 star property
    9.2/10 - Wonderful (92 reviews)
    "The hotel is fairly new so the property is well kept. The entire staff I came in contact with was very helpful and attentive. Location is ideal, walking distance to a Top Golf and entertainment facility for kids and adults in the evening and very close to the highway. My only one complaint is that the hotel does not provide a pot or pan for cooking on the electric range. I was there for a little over a week and that would've been very helpful. I did appreciate the microwave and apartment size..."
    Reviewed November 4, 2026
    Roundtrip • New York (EWR) - Greensboro (GSO)
    EWR - GSO • Nonstop GSO - EWR • 1 stop
    $740
    $525
    per traveler
    found 16 hours ago
    StudioRes by Marriott Greensboro Airport
  • A spacious indoor area with multiple dining tables and chairs, a central staircase, and large windows allowing natural light.
    Jan 13 - Jan 18

    Proximity Hotel + Flight

    Greensboro
    5 nights
    4.0 star property
    9.8/10 - Exceptional (1,002 reviews)
    Roundtrip • New York (EWR) - Greensboro (GSO)
    EWR - GSO • Nonstop GSO - EWR • 1 stop
    $1,191
    $878
    per traveler
    found 16 hours ago
    Proximity Hotel
  • A hotel with a prominent entrance, a covered walkway, and a flag on top.
    Jan 13 - Jan 18

    O.Henry Hotel + Flight

    Greensboro
    5 nights
    4.0 star property
    9.8/10 - Exceptional (880 reviews)
    "We absolutely love staying here!!! We feel very pampered!!! Everything here is amazing!! The beds, service, food, room, showers are excellent!!"
    Reviewed November 3, 2026
    Roundtrip • New York (EWR) - Greensboro (GSO)
    EWR - GSO • Nonstop GSO - EWR • 1 stop
    $1,273
    $969
    per traveler
    found 16 hours ago
    O.Henry Hotel
  • Outdoor dining
    Dec 11 - Dec 14

    Pandora's Manor Bed & Breakfast + Flight

    West High Avenue Historic District
    3 nights
    3.5 star property
    10/10 - Exceptional (4 reviews)
    "Thanks for a wonderful stay. The property is beautiful and well kept. I was able to get some peace and quiet while attending GHOE and checking on the remodeling of one of my rental properties. I got the best rest during my stay. The property is safe and secure. The staff was very attentive and friendly. Definitely a home away from home. Will stay again."
    Reviewed November 1, 2026
    Roundtrip • Chicago (ORD) - Greensboro (GSO)
    ORD - GSO • Nonstop GSO - ORD • Nonstop
    $1,344
    $1,076
    per traveler
    found 8 hours ago
    Pandora's Manor Bed & Breakfast
  • A dining table with a bottle of wine, two glasses, a candle, and a decorative glass dome over a plant.
    Jan 13 - Jan 18

    The Historic Magnolia House + Flight

    Greensboro
    5 nights
    3.5 star property
    7.4/10 - Good (3 reviews)
    Roundtrip • New York (EWR) - Greensboro (GSO)
    EWR - GSO • Nonstop GSO - EWR • 1 stop
    $1,193
    $995
    per traveler
    found 16 hours ago
    The Historic Magnolia House

Midway Hotel Deals

A conference room with a long table, black leather chairs, and a projector screen.

The Historic Brookstown Inn, Trademark Collection by Wyndham

The Historic Brookstown Inn, Trademark Collection by Wyndham
3.5 star property
8.3 mi from Midway
9.6 out of 10, Exceptional, (1,001 reviews)
$120 nightly
The price is $135
Nov 22 - Nov 23
Total with taxes and fees
The Historic Brookstown Inn, Trademark Collection by Wyndham
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.
See all properties in Midway

Frequently Asked Questions

How much does a Midway vacation package cost?

You can snap up a vacation package to this popular destination from $525 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.