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.
La Quinta Inn & Suites by Wyndham Greensboro Arpt High Point

La Quinta Inn & Suites by Wyndham Greensboro Arpt High Point

3 out of 5
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
8.8/10 Excellent! (1,002 reviews)
I didn’t care for their breakfast

Reviewed on Aug. 1, 2025

Julian Price House

Julian Price House

3 out of 5
Fisher Park
per person
Sep 5 - Sep 7
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
10/10 Exceptional! (101 reviews)
This place is absolutely beautiful, everything was perfect

Reviewed on Jul. 26, 2025

Proximity Hotel

Proximity Hotel

4 out of 5
per person
Oct 2 - Oct 6
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
9.6/10 Exceptional! (816 reviews)
Beautiful hotel and dining

Reviewed on Jul. 29, 2025

O.Henry Hotel

O.Henry Hotel

4 out of 5
per person
Oct 2 - Oct 6
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
9.8/10 Exceptional! (683 reviews)
The design of the hotel and the special events like Jazz night and Tea in the afternoon were a delight.

Reviewed on Jul. 21, 2025

Wingate by Wyndham High Point

Wingate by Wyndham High Point

2.5 out of 5
Deep River
per person
Oct 2 - Oct 6
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
7.8/10 Good! (1,004 reviews)
Everything was good

Reviewed on Jul. 29, 2025

Ready to book your vacation to Winston-Salem?

 

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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 $96 per night from Aug 3 to Aug 4
CA $96
CA $108 total
Aug 3 - Aug 4
includes taxes & fees
8/10 Very Good! (1,006 reviews)
"Nice room we only stayed for a night, did smell like cigarette smoke but not bad, honestly an underrated gem. Had a pool too which was nice and super friendly staff!"

Reviewed on Aug. 1, 2025

Hawthorne Inn and Conference Center
Best Western Plus University Inn

Best Western Plus University Inn

3.5 out of 5
3050 University Pkwy, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Aug 5 to Aug 6
CA $111
CA $126 total
Aug 5 - Aug 6
includes taxes & fees
7.2/10 Good! (1,000 reviews)
"Staff was excellent"

Reviewed on Jul. 29, 2025

Best Western Plus University Inn
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 $139 per night from Aug 31 to Sep 1
CA $139
CA $158 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (551 reviews)
"Property very clean. Check-in seamless and fresh cookies were great. Breakfast food was cold. There was no waffle mix but oatmeal and other cold options ok"

Reviewed on Jul. 27, 2025

Hampton Inn & Suites Winston-Salem Downtown
See all 1,326 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

What to do in Winston-Salem

Lantern Light and Spooky Stories

Carolina History & Haunts Winston-Salem Historical Ghost Tour

CA $36
per adult
100% of travellers recommend
Carolina History & Haunts Winston-Salem Historical Ghost Tour
See all activities in Winston-Salem

Frequently asked questions

How much does a Winston-Salem vacation package cost?
You'll find cheap prices from CA $692 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.