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 $4,200 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.
O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was CA $1,409, price is now CA $1,201 per person
CA $1,201
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
9.8/10 Exceptional! (801 reviews)
breakfast wasn’t that great

Reviewed on Jun 3, 2026

Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade

4 out of 5
Price was CA $3,123, price is now CA $2,678 per person
CA $2,678
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
8/10 Very Good! (1 review)
The house was very clean, comfortable, and nicely maintained, which we really appreciated during our stay. However, there were two downsides to be aware of. First, after booking, the owner asked us to pay an extra money for cleaning fee, even though it was not clearly listed in the Expedia booking details. I chose not to argue since I didn’t want to ruin our family trip, but future guests should expect additional charges. Second, privacy was an issue the owner lives in the basement, and it felt uncomfortable at times, especially with my child playing and moving around. Overall, it’s a nice property, but keep in mind the extra costs and limited privacy.

Reviewed on Sep 30, 2025

Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub

4 out of 5
Price was CA $2,598, price is now CA $2,249 per person
CA $2,249
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
No reviews
Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub

4 out of 5
Price was CA $2,585, price is now CA $2,238 per person
CA $2,238
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
No reviews
King Bed Pet Friendly BBQ Grill Peaceful

King Bed Pet Friendly BBQ Grill Peaceful

4 out of 5
Price was CA $2,487, price is now CA $2,154 per person
CA $2,154
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
8/10 Very Good! (1 review)

Ready to book your vacation to Winston - Salem?

 

Choose your dates

Winston - Salem Hotel Deals

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 $108 per night from Jun 23 to Jun 24
CA $108
CA $122 total
Jun 23 - Jun 24
includes taxes & fees
8.6/10 Excellent! (1,123 reviews)
"Clean room"

Reviewed on Jun 11, 2026

Hawthorne Inn and Conference Center
Suburban Studios Winston Salem-University Parkway

Suburban Studios Winston Salem-University Parkway

2 out of 5
7910 N Point Blvd Winston-Salem NC
Fully refundableReserve now, pay when you stay
The price is CA $69 per night from Jun 18 to Jun 19
CA $69
CA $78 total
Jun 18 - Jun 19
includes taxes & fees
5.8/10 (999 reviews)
"Thanks for your hospitality"

Reviewed on Jun 8, 2026

Suburban Studios Winston Salem-University Parkway
Sleep Inn Hanes Mall

Sleep Inn Hanes Mall

2.5 out of 5
1985 Hampton Inn Ct Winston-Salem NC
Fully refundable
The price is CA $106 per night from Jul 5 to Jul 6
CA $106
CA $123 total
Jul 5 - Jul 6
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"Upon arrival, the grounds were full of broken glass and trash. Uppn check in the front desk attendant got visibily annoyed that i didnt have a "card" for my service dog and she refused to allow me to stay on an upper floor due to my "pets must go on first floor". First room assigned the door was ..."

Reviewed on Jun 9, 2026

Sleep Inn Hanes Mall
See all 599 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

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

BB&T Soccer Park

Explore the great outdoors at BB&T Soccer Park, a lovely green space in Advance. Visit the shops in this family-friendly area, or simply enjoy its restaurants.

BB&T Soccer 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.