Winston - Salem Vacation Packages

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Top Winston - Salem Vacation Deals

Price found within the past 48 hours. Click for updated prices.
OYO Inn Kernersville

OYO Inn Kernersville

2.5 out of 5
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

Julian Price House

3 out of 5
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

Hawthorne Inn and Conference Center

3 out of 5
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

DoubleTree by Hilton Greensboro Airport

DoubleTree by Hilton Greensboro Airport

4 out of 5
Price was CA $2,003, price is now CA $1,593 per person
CA $1,593
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Greensboro (GSO)
9/10 Wonderful! (570 reviews)
I enjoyed my stay at this hotel.

Reviewed on Aug. 19, 2025

O.Henry Hotel

O.Henry Hotel

4 out of 5
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

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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 $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

Hawthorne Inn and Conference Center
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 $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

DoubleTree by Hilton Winston Salem - University
Courtyard by Marriott Winston-Salem University

Courtyard by Marriott Winston-Salem University

3 out of 5
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

Courtyard by Marriott Winston-Salem University
See all 565 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
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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

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?
Maybe less than you might think — from a low CA $912, actually! By bundling flights, hotels and car rentals into your own customized vacation package, your Winston - Salem escape is only clicks away.
How do I get a cheap travel package to Winston - Salem?
Think of all the fun things you could do in Winston - Salem with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your flights, hotels and other bookings into a Winston - Salem vacation package. You have plenty of choice when it comes to booking with Expedia too. In fact, you can choose from more than 550 air carriers and 1,000,000 hotel options around the world. Whether you're enjoying a break with the entire family or going it alone, planning a trip to Winston - Salem is better with a package.
Where should I stay in Winston - Salem?
If it's your first visit to Winston - Salem, head for Winston-Salem. This top neighborhood boasts some fantastic sights, like Wake Forest University.
What are the top hotels in Winston - Salem?
Best Western Plus Hanes Mall Hotel in the Winston-Salem neighborhood is a terrific choice for a Winston - Salem getaway. Reserve a room here and you'll be well-placed to get out and explore all that this colorful city has to offer.
How far in advance should I book my Winston - Salem vacation?
It can be difficult to know when is the perfect time to book your vacation to Winston - Salem. But usually the earlier you book, the lower the prices. Sometimes, you can reserve your flights and hotels up to a year prior to departure. If you're considering a last-minute getaway, no need to panic! There are fantastic bargains advertised on Expedia every day.
What does an Expedia Winston - Salem travel package include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply choose your favorite bundle and gain access to great discounts. Once you've made your booking, add on a couple of sightseeing tours and watch your savings pile up. When it comes to creating your Winston - Salem getaway, the choice is all yours!
What should I know before booking a Winston - Salem travel package?
So many places to venture to, so many things to see. With a package, you can cross more of them off your list. Combine your flights, hotels and rental cars and make big savings.
Can I choose my airline with a Winston - Salem Expedia vacation package?
Definitely. Expedia has more than 550 partner airlines to choose from globally. With such a big range of choice, finding the ideal carrier to whisk you away to Winston - Salem will be a breeze.
If I'm not able to travel, can I cancel my Winston - Salem vacation package?
Whether it's your hotel, flight or rental car, you can cancel and rebook it. Locked in your Winston - Salem vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings made more than 24 hours ago, you may incur a fee from your airline, hotel or car rental company. For further information, head to our Customer Service Portal. We're here to help you each step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.