
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.

OYO Inn Kernersville
Price was CA $1,039, price is now CA $912 per person
CA $912
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
7/10 Good! (354 reviews)
Pam and Kristin are dedicated to guests feeling comfortable and keep the establishment clean and tidy. Thank you again!!
Reviewed on Aug. 18, 2025

Julian Price House
Fisher Park
Price was CA $4,243, price is now CA $1,352 per person
CA $1,352
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
10/10 Exceptional! (102 reviews)
The staff was very detailed and organized with my arrival being that I flew in from KY at midnight. The interior and exterior design is EXQUISITE! My communication with the staff was always very pleasant and professional via text. I will be booking another stay the next time I’m in NC.
Reviewed on Aug. 15, 2025

Hawthorne Inn and Conference Center
Price was CA $1,563, price is now CA $1,072 per person
CA $1,072
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Greensboro (GSO)
8.2/10 Very Good! (1,001 reviews)
I have never been to a hotel that had no one at the front desk. I waited several minutes before two people came from another part of the hotel. There was no signage to tell you to wait or give an explanation. There was no music or any indication there was anyone about. I was told they have to do periodic ‘rounds’. Ok. But. I was processed and given my key card. I did not feel welcome and I had to ask about the breakfast. The hallway was long and narrow. No one around. Creepy. I have traveled to Europe and never had this experience. I won’t go back.
Reviewed on Aug. 18, 2025


O.Henry Hotel
Price was CA $2,105, price is now CA $1,700 per person
CA $1,700
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
9.8/10 Exceptional! (685 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
Winston - Salem Hotel Deals

Hawthorne Inn and Conference Center
420 High St, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Aug 24 to Aug 25
CA $110
CA $124 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Very nice and affordable. The only issue I had was the power kept going in and out"
Reviewed on Aug. 18, 2025

DoubleTree by Hilton Winston Salem - University
5790 University Pkwy, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Aug 27 to Aug 28
CA $142
CA $160 total
Aug 27 - Aug 28
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"The water feature was not in operation. The staff was kind the bed was comfortable. The room was clean and so were most of the common areas but the pool needed a little upkeep. There were cigerett"
Reviewed on Aug. 6, 2025

Courtyard by Marriott Winston-Salem University
3111 University Pkwy, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Aug 27 to Aug 28
CA $131
CA $149 total
Aug 27 - Aug 28
includes taxes & fees
8.4/10 Very Good! (719 reviews)
"I already wrote them a 5 star review on yelp but this was hands down the best chain hotel experience we have had. It started as soon as we checked in. Every single employee that we encountered at this hotel was genuinely kind and went out of their way to greet us or start a conversation with us. ..."
Reviewed on Aug. 14, 2025
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.
Discover the most popular places to visit in Winston - Salem

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.
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.
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.
What to do in Winston - Salem

Carolina History & Haunts Winston-Salem Historical Ghost Tour
CA $36
per adult
100% of travellers recommend
Frequently asked questions
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
Expedia's Latest Trends
Hotels
Flights
Cars
Activities
Packages
Vacation Rentals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.