Winston-Salem Vacations from $538

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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.
O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $648, price is now $538 per person
$538
per person
Aug 21 - Aug 23
found 14 hours ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
9.8/10 Exceptional! (819 reviews)
Wish you would have: 1. Freezers with you mini fridge 2. Breakfast starting at 6 am Otherwise fantastic

Reviewed on Jun 27, 2026

Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was $917, price is now $692 per person
$692
per person
Aug 14 - Aug 18
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Greensboro (GSO)
10/10 Exceptional! (139 reviews)
Very well maintained, extremely clean property. Exceptionally responsive host who checked in frequently regarding stay. Location was great- beautiful park across the street and close to downtown. Water pressure in shower was a little low. Highly recommend!

Reviewed on Jun 26, 2026

Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade

4.5 out of 5
Save 100% on your flight
Price was $1,834, price is now $1,501 per person
$1,501
per person
Aug 21 - Aug 23
found 14 hours ago
Roundtrip flight included
New York (NYC) 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

Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub

4 out of 5
Price was $1,490, price is now $1,236 per person
$1,236
per person
Aug 21 - Aug 23
found 14 hours ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
No reviews
King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit

4.5 out of 5
Price was $1,228, price is now $1,026 per person
$1,026
per person
Aug 21 - Aug 23
found 14 hours ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
9.4/10 Exceptional! (3 reviews)
Loved this little house and all the attention to detail! Would definitely return.

Reviewed on Jun 17, 2026

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Stay near popular Winston-Salem attractions

An aerial view of a city with red-roofed buildings, green parks, and a distant city skyline.

Old Salem

8.6/5 (723 reviews)
Step back in time at this preserved Moravian settlement where costumed interpreters bring 18th-century life to vivid reality. Savor traditional treats from the historic Winkler Bakery while strolling cobblestone streets.
See properties

What to do in Winston-Salem

Winston-Salem True Crime Tour

Winston-Salem True Crime Tour

$19
per adult
Winston-Salem True Crime Tour
Carolina History & Haunts Winston-Salem Historical Ghost Tour

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
$83 nightly
The price is $94 total per night from Jul 7 to Jul 8
$94 total
Jul 7 - Jul 8
Total with taxes and fees
8.6/10 Excellent! (1,146 reviews)
"Staff was very friendly and helpful"

Reviewed on Jun 25, 2026

Hawthorne Inn and Conference Center
Suburban Studios Winston Salem-University Parkway

Suburban Studios Winston Salem-University Parkway

2 out of 5
7910 N Point Blvd Winston-Salem NC
Fully refundableReserve now, pay when you stay
$47 nightly
The price is $53 total per night from Jul 27 to Jul 28
$53 total
Jul 27 - Jul 28
Total with taxes and fees
5.8/10 (1,003 reviews)
"This place was under renovation found screws in parking room dirty shower dirty stove dirty lining stained no bugs was the only good part plus it was cheap the only thing I could afford emergency trip elevator constantly not functioning switched rooms it was just as bad. Staff extremely nice however ..."

Reviewed on Jun 27, 2026

Suburban Studios Winston Salem-University Parkway
Best Western Plus Hanes Mall Hotel

Best Western Plus Hanes Mall Hotel

2.5 out of 5
3330 Silas Creek Pkwy Winston-Salem NC
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $85 total per night from Jul 1 to Jul 2
$85 total
Jul 1 - Jul 2
Total with taxes and fees
7.6/10 Good! (1,004 reviews)
"Loved it"

Reviewed on Jun 25, 2026

Best Western Plus Hanes Mall Hotel
See all 1,444 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.

Find the Best Winston-Salem Vacation Packages

Winston-Salem Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Piedmont Triad Intl. Airport (GSO)
Population
241,200
Max Temp Winter
50ºF
Max Temp Summer
90ºF
Top Sights
Reynolda House Museum of American Art, Airbound Trampoline Park and SciWorks

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Frequently asked questions

How much does a Winston-Salem vacation package cost?
Offering great value package deals from $538 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.