Winston - Salem Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Visit Winston Salem

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Winston - Salem Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Wyndham Garden Greensboro

Wyndham Garden Greensboro

3 out of 5
Price was CA $1,384, price is now CA $1,163 per person
CA $1,163
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
7.8/10 Good! (1,003 reviews)
This is the cleanest and most organized hotel I’ve ever been to! Very affordable!

Reviewed on Apr 10, 2026

Hampton Inn Greensboro-Airport

Hampton Inn Greensboro-Airport

3 out of 5
Price was CA $1,811, price is now CA $1,411 per person
CA $1,411
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
8.8/10 Excellent! (780 reviews)
Friendly staff. Good breakfast and coffee available all day and night.

Reviewed on Apr 2, 2026

O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was CA $2,327, price is now CA $1,877 per person
CA $1,877
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
9.8/10 Exceptional! (776 reviews)
Our favorite hotel - always wonderful and always consistent - the friendliest, most accommodating staff and lots of places to relax

Reviewed on Apr 5, 2026

Proximity Hotel

Proximity Hotel

4 out of 5
Price was CA $2,372, price is now CA $1,946 per person
CA $1,946
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
9.8/10 Exceptional! (975 reviews)
This establishment is the best in the city. Me and my family enjoy it so much, it’s our third time staying there. I hope to soon do a honeymoon weekend that they offer.

Reviewed on Apr 5, 2026

La Quinta Inn & Suites by Wyndham Greensboro NC

La Quinta Inn & Suites by Wyndham Greensboro NC

3 out of 5
Price was CA $1,487, price is now CA $1,268 per person
CA $1,268
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
8/10 Very Good! (1,003 reviews)
We liked how spacious the room was and the size of the mini fridge was perfect, not like the extremely small outdated ones. Our only complaint was the size of the toilet, it is quit small and low to the ground. Overall we enjoyed our stay.

Reviewed on Apr 12, 2026

Ready to book your vacation to Winston - Salem?

 

Choose your dates

Winston - Salem Hotel Deals

DoubleTree by Hilton Winston Salem - University

DoubleTree by Hilton Winston Salem - University

4 out of 5
5790 University Pkwy Winston-Salem NC
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from May 3 to May 4
CA $152
CA $171 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
The staff that I encountered were all very welcoming and professional. My junior king suite was spacious, clean and the bed was complete.

Reviewed on Apr 6, 2026

DoubleTree by Hilton Winston Salem - University
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
The price is CA $117 per night from Apr 14 to Apr 15
CA $117
CA $132 total
Apr 14 - Apr 15
includes taxes & fees
8.4/10 Very Good! (1,045 reviews)
Per booking the breakfast was free, however per hotel staff it was a charge per person.

Reviewed on Apr 12, 2026

Hawthorne Inn and Conference Center
Hampton Inn & Suites Winston-Salem Downtown

Hampton Inn & Suites Winston-Salem Downtown

2.5 out of 5
235 North Cherry Street Winston-Salem NC
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Apr 19 to Apr 20
CA $200
CA $226 total
Apr 19 - Apr 20
includes taxes & fees
9/10 Wonderful! (709 reviews)
This stay was unexpected because my Mom had to go to the hospital in Winston-Salem when she fell and broke her hip. We were traveling with our two small dogs and I had a difficult time finding a pet friendly hotel. Thank goodness I was able to stay at this location near the hospital. Everyone at ...

Reviewed on Apr 10, 2026

Hampton Inn & Suites Winston-Salem Downtown
See all 609 properties in Winston - Salem
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Winston - Salem

Bowman Gray Stadium

Bowman Gray Stadium

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

Wake Forest University Baptist Medical Center

Though Wake Forest University Baptist Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winston-Salem while you are here.

Wake Forest University Baptist Medical Center

Tanglewood Park

Explore the great outdoors at Tanglewood Park, a lovely green space in Clemmons. Attend a sporting event or simply enjoy the local cheese shops while you're in the area.

Tanglewood Park

Frequently asked questions

Can I cancel my flight booking to Winston - Salem due to COVID-19?
Our handy Customer Service Portal is your one-stop shop for almost every travel question, including about flight cancellations and changes due to COVID-19. For extra peace of mind, we suggest reading through the terms and conditions of your fare before booking a seat.
What's the best way to find cheap flights to Winston - Salem that have flexible change policies?
It's quick and easy with Expedia. First, enter your travel dates and press "Search." Step 2: Check "No change fee" directly under the "Flexible change policies" subheading to the left of your screen. Step 3. Score your cheap and flexible ticket to Winston - Salem.
What are some of the general tips for travelers to Winston - Salem during the COVID-19 outbreak?
The COVID-19 outbreak has changed how we travel, but it hasn't stopped our zest for exploring. Here are some tips on how to deal with the new challenges of traveling:
  • Before you lock in a flight, find out if any travel bans or restrictions apply — in both your destination and origin. Stay informed with the latest updates by reviewing government and airport websites.
  • You must wear a face mask throughout your travel experience, even at screening checkpoints. Be prepared to lower your mask for ID verification when asked.
  • Rather than handing a TSA officer your boarding pass, position it straight on the scanner yourself. Then, hold it up for inspection.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on bags. This will need to be removed from your bag and presented for screening.
  • To minimize handling during the screening process, put items such as your phone, keys and wallet into your carry-on rather than into the bins.
  • Transport your food items in a clear plastic bag and also put them in a screening bin. Keeping your food separate from your carry-on means it's less likely a TSA agent will need to open and touch your bag for inspection.

Which airlines fly to Winston - Salem?
Let American Airlines take you there. This leading carrier offers 560 services a month to Piedmont Triad Intl. Airport (GSO), a Winston - Salem gateway.
How can I find cheap tickets to Winston - Salem?
Book well ahead, consider alternative airports, use frequent flyer miles — there are plenty of ways! Another one is to make the most of Expedia's "flexible dates" feature. Search for a Winston - Salem flight, then check out the cheapest prices for nearby dates. In the last seven days, the best price for a flight to Winston - Salem was .
How much is a flight to Winston - Salem?
In the last seven days, return flights to Winston - Salem sold for as low as and peaked at . For one-way fares departing from (), the lowest amount paid during this time was .
How many airlines fly to Winston - Salem?
There are 5 airlines that service Winston - Salem from 14 airports around the world.
Which airlines fly to Winston - Salem?
Flights to Winston - Salem are typically run by American Airlines. The majority of these flights set off from Charlotte, with American Airlines servicing this route the most often.
How many nonstop flights are there to Winston - Salem?
Flying to a new place is much more fun when there aren't any stopovers involved. If you're jetting off to Winston - Salem, the good news is that there are around 221 direct flights operating every week.
Where are the most popular flights to Winston - Salem departing from?
The most popular flights to Winston - Salem set off from Charlotte, Atlanta and Chicago airports.
How long is the flight to Winston - Salem Airport?
If it's Charlotte you're departing, you'll be airborne for around 58 minutes before you touchdown in Winston - Salem. Tarmac to tarmac from Atlanta takes approximately 1 hour and 19 minutes and from Chicago, the average flight time is 1 hour and 57 minutes.
How to book the cheapest flight to Winston - Salem?
Don't leave booking your flight to Winston - Salem until the last moment. That's one trick frequent travelers use to get the best deals. Booking in advance means more choices and cheaper flights. Also, shop around and compare your options. If your destination has a few airports, you may be able to nab a terrific deal by flying into one a little farther out. And finally, don't forget that it's first in, best dressed. Familiarize yourself with airfare costs and have your credit card ready to grab your ticket as soon as you spot an unbeatable bargain. The sweetest deals never last long.
How to survive the flight to Winston - Salem?
If you're poorly prepared, airports and flying can be daunting. But there's no need to hit the panic button just yet. Follow these tips and tricks and enjoy a hassle-free start to your time in Winston - Salem.What to pack in your hand luggage:
  • A plane ride can be easy if you've got all the right gear. First things first, you'll need basic toiletry items, such as a toothbrush and lip balm, a fresh change of clothes and a magazine or two. Secondly, make room in your carry-on bag for your mobile phone, a charger, your important medications and maybe a proper neck pillow too. Lastly, don't forget to bring your passport, travel docs and some cash.
  • Put all your full-sized bottles of hair gel and hairspray in your checked baggage. Any liquids or gels in your carry-on bag larger than 3.4 ounces (100 milliliters) will be confiscated by authorities. Pointed or sharp objects, like your precious Swiss Army knife, and dangerous goods which are flammable or explosive, such as spray paint, flares and fuels, are also restricted.
  • The aisles of your aircraft are no fashion runway. Don comfortable layers and remember to bring a cardigan as it can get chilly inside the cabin during long-haul flights. Closed-toed, flat shoes are always a good idea too.
  • Most travelers are aware of DVT (deep vein thrombosis), a blood clotting condition caused by long periods of inactivity. There are plenty of ways to reduce your risk. Wear a pair of compression tights or socks, stay hydrated and move your legs and feet. Wander around the cabin or try out some simple stretches in your seat.

How to get through airport security fast when flying to Winston - Salem?
A little pre-planning before your flight will make your getaway to Winston - Salem easy and painless. Read through our handy tips for a swift journey through security:
  • Airport security personnel first need to see that you have a valid ID and boarding pass before anything else. Have them ready for inspection.
  • The X-ray machine is up next. Remove anything on you that is likely to set off the scanner's alarm. This includes things like headphones or earphones, as well as heavy coats or jackets. They'll all need to go on the X-ray conveyor belt.
  • For just a few moments, you'll have to unplug from technology. Your phone, laptop and any other electronics must also be sent through the scanner.
  • Want to bring along your favorite perfume? No problem. As long as the volume is no larger than 3.4 ounces (100 milliliters) and it's stored in a clear zip-lock bag, you're allowed to bring it with you in your carry-on.
  • It's also likely that you'll need to remove your shoes to be X-rayed, so wearing slip-on shoes is always a smart idea.
  • Sharp or pointed objects (like knives and scissors) are not allowed on board. They'll be confiscated at security, so pack them safely away in your checked suitcase.

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.