Winston-Salem Vacations from $526

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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.

The Latest Winston-Salem vacation packages

Price found within the past 48 hours. Click for updated prices.
Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was $1,831, price is now $526 per person
$526
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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

O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $870, price is now $618 per person
$618
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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

Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub

3.5 out of 5
Save 100% on your flight
Price was $3,014, price is now $2,162 per person
$2,162
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Greensboro (GSO)
No reviews
Wyndham Garden Greensboro

Wyndham Garden Greensboro

3 out of 5
Price was $795, price is now $598 per person
$598
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Greensboro (GSO)
7.6/10 Good! (1,007 reviews)
Staff was very efficient and the facility is recently remodeled and very clean!

Reviewed on Aug 19, 2025

The Historic Magnolia House

The Historic Magnolia House

3.5 out of 5
Price was $780, price is now $589 per person
$589
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Greensboro (GSO)
6/10 (2 reviews)
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Discover the most popular places to visit in Winston-Salem

First Methodist Church

Old Salem

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.

Old Salem
Awesome racing!

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
Tropical in the greenhouse

Reynolda Gardens

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.

Reynolda Gardens

What to do in Winston-Salem

Winston-Salem True Crime Tour

Winston-Salem True Crime Tour

$19
per adult
Winston-Salem True Crime Tour
Lantern Light and Spooky Stories

Carolina History & Haunts Winston-Salem Historical Ghost Tour

$26
per adult
100% of travellers recommend
Carolina History & Haunts Winston-Salem Historical Ghost Tour
See all activities in Winston-Salem

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
$79 nightly
The price is $89 total per night from Aug 24 to Aug 25
$89 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (1,016 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
$102 nightly
The price is $116 total per night from Aug 26 to Aug 27
$116 total
Aug 26 - Aug 27
Total includes taxes and 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
$95 nightly
The price is $107 total per night from Aug 27 to Aug 28
$107 total
Aug 27 - Aug 28
Total includes taxes and 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 1,337 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.

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Frequently asked questions

How much does a Winston-Salem vacation package cost?
Offering great value package deals from $526 on Expedia, you'll be surprised at how little a vacation to Winston-Salem costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Winston-Salem?
September, November and December are the best times to search for cheap Winston-Salem vacation packages. Choosing to travel in quieter months means you'll typically find better prices on flights and hotels.
How many days is enough for Winston-Salem?
You can easily visit all the top sights in Winston-Salem within a few days, including the must-see Southeastern Center for Contemporary Art. If you're after an extended Winston-Salem vacation, look at what sort of day tours and activities are available in the area.
Is it worth booking a vacation package to Winston-Salem?
Well known for its culture, history and nature, a Winston-Salem vacation is a hit with all kinds of visitors. Be sure to check out top sights like Lawrence Joel Veterans Memorial Coliseum and Old Salem, and consider renting a set of wheels for day trips to experience even more.
How to find the best Winston-Salem package deals?
Bagging a cheap Winston-Salem package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Winston-Salem package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winston-Salem vacation as a package?
You can enjoy significant savings on your next Winston-Salem getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Winston-Salem?
Secure fantastic discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Winston-Salem trip.
How to plan a trip to Winston-Salem?

  1. Choose when to travel: Check your calendar and get packing. Your favorite time of year and the type of activities available will also help you decide when to escape to Winston-Salem.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to flights and activities. Your hotel will probably be the biggest expense during your trip to Winston-Salem.
  3. Use Expedia's trip planning tool to discover Winston-Salem: Research every part of your trip to Winston-Salem with this handy planner. Invite your family and friends to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you're up to speed on Winston-Salem, you can figure out the ideal length of your break. Put together a draft itinerary and allocate enough time for all the things you want to do.
  5. Combine your airfare and accommodations: After you've settled on your trip dates and duration, book the right Winston-Salem vacation package for you.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some fun things to do in Winston-Salem in Winston-Salem. Book tickets or make reservations in advance to save time and avoid the stress of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Winston-Salem vacation packages?
Your Winston-Salem getaway should be an escape from your daily routine, not a reason for money worries. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.