Winston-Salem Vacation Packages
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Your Winston-Salem Vacation
Take away the hard part of organizing your next amazing adventure with a Winston-Salem vacation package. Whether you're lured here by its cuisine, history, art or something else, this city offers countless exciting experiences to delve into. Make your trip to Winston-Salem even more enjoyable by going sightseeing. Wake Forest University, Hanes Mall and Old Salem are some of the most popular attractions worth exploring. Check out Expedia's extensive range of travel options and book your dream vacation to Winston-Salem today.
Top Winston-Salem Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Heated Pool King Bed Jacuzzi Bath Arcade
CA $5,096
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Calgary (YYC) 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
King Beds Hot Tub Arcade Grill & Firepit
CA $3,331
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Greensboro (GSO)
9.4/10 Exceptional! (3 reviews)
This home is nice and in a nice location. We were however confused that it was listed as a whole house with a hot tub, but you have to pay a fee for the hot tub, and in fact there was a whole other rental below us. The charges for an extra guest to visit were a little much also. It wasn't very clean, we found random items stuffed and placed on top of cabinets, light fixtures etc. and a cup under the bed. Lastly, to be asked to sparingly use utilities so they can save on bills is way out of line. I didn't go on vacation to hear about your financial situation. It's a rental. I'm not taking my shoes off, and I'm not turning the air off when I'm gone. We came into the house at 85 degrees.
Reviewed on Sep 8, 2026
DoubleTree by Hilton Greensboro Airport
CA $2,778
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Greensboro (GSO)
8.8/10 Excellent! (1,430 reviews)
Very friendly, helpful employees. The bed and pillows were very comfortable and my room was large and clean. I’ll definitely stay here again.
Reviewed on Sep 8, 2026
Ready to book your vacation to Winston-Salem?
Winston-Salem Hotel Deals
Hawthorne Inn and Conference Center
420 High St Winston-Salem NC
Fully refundableReserve now, pay when you stay
CA $97
CA $110 total
Sep 10 - Sep 11
includes taxes & fees
8.6/10 Excellent! (1,222 reviews)
"Tge room needed more light."
Reviewed on Sep 8, 2026
Suburban Studios Winston Salem-University Parkway
7910 N Point Blvd Winston-Salem NC
CA $65
CA $73 total
Oct 8 - Oct 9
includes taxes & fees
La Quinta Inn & Suites by Wyndham Winston-Salem
2020 Griffith Rd Winston-Salem NC
Fully refundableReserve now, pay when you stay
CA $94
CA $107 total
Sep 13 - Sep 14
includes taxes & fees
7.4/10 Good! (250 reviews)
"I loved the convenience of the location and it is a beautiful hotel"
Reviewed on Sep 8, 2026
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.
Stay near popular Winston-Salem attractions
Old Salem
8.6/10 (723 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.
Photo by Melanie E
Bowman Gray Stadium
8.4/10 (7 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.
Photo by Cynthia Phillips
Reynolda Gardens
9.0/10 (139 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.
Hanes Mall
8.4/10 (1,145 reviews)
You can do some window-shopping at Hanes Mall during your stay in Winston-Salem. Attend a sporting event or simply enjoy the local cheese shops while you're in the area.
Benton Convention Center
8.2/10 (241 reviews)
Learn about the events happening at Benton Convention Center during your trip to Winston-Salem. Amble around this family-friendly area's lush forest or attend a sporting event.
Lawrence Joel Veterans Memorial Coliseum
8.0/10 (281 reviews)
Catch an event at Lawrence Joel Veterans Memorial Coliseum during your trip to Winston-Salem. Amble around this family-friendly area's lush forest or attend a sporting event.
Truist Stadium
8.4/10 (363 reviews)
Catch an event at Truist Stadium during your trip to Winston-Salem. Amble around this romantic area's lush forest or attend a sporting event.
Reynolda House Museum of American Art
You can spend time browsing the exhibits at Reynolda House Museum of American Art during your travels in Winston-Salem. Amble around the area's lush forest or attend a sporting event.
Frequently asked questions
How much does a Winston-Salem vacation package cost?
You'll find cheap prices from CA $2,214 on Expedia for your Winston-Salem getaway. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Winston-Salem costs.
What are the cheapest months to go to Winston-Salem?
December, January and February are the best times to look for cheap Winston-Salem vacation packages. Travelling in less busy months means you can usually find lower prices on flights and hotels.
How many days is enough for Winston-Salem?
For a Winston-Salem vacation, a handful of days will be enough to see the top spots. Be sure to check out Old Salem — it's one of the major attractions in this destination. If you're looking for more activities, consider basing yourself here and going on some day tours from Winston-Salem.
Is it worth booking a vacation package to Winston-Salem?
Popular for its walking trails, cycling and fishing, a Winston-Salem vacation is a hit with all kinds of travellers. Be sure to visit leading sights like Lawrence Joel Veterans Memorial Coliseum and Old Salem, and consider renting a car for day trips to experience even more.
How to find the best Winston-Salem package deals?
Begin your search for a Winston-Salem package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Winston-Salem package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winston-Salem adventure underway.
Is it cheaper to book a Winston-Salem vacation as a package?
You can enjoy significant savings on your next Winston-Salem escape by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to view the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winston-Salem?
If you've got your Winston-Salem travel dates locked in, book as soon as you can to score some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Winston-Salem?
- Choose when to get away: Check your calendar and pack your bags. Your favourite time of year and the activities on offer will also help you decide when to escape to Winston-Salem.
- Set a budget: Consider expenses like transportation, flights and meals when calculating how much to put aside for your trip to Winston-Salem. Then, pick a property that matches your budget, whether that's a wallet-friendly stay or a deluxe getaway.
- Decide how many days away: Start by making a list of all the sights and activities you'd like to experience in Winston-Salem. Then, estimate how long you'll need at each, along with any travel time.
- Combine your accommodations and airfare: After you've settled on your dates and duration, book the right Winston-Salem vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
