Winston-Salem Vacations from $481

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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

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.
Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
Price was $541, price is now $481 per person
$481
per person
Apr 17 - Apr 19
found 6 hours ago
Roundtrip non-stop flight included
New York (JFK) to Greensboro (GSO)
8.4/10 Very Good! (1,007 reviews)
Very clean rooms, staff readily accessible.. Well lit parking areas. Friendly staff, many dining choices to choose from within walking distance. Beautiful view of the skyline. I enjoyed my multi day stay, very professional staff members and quiet environment. Thanks so much to the staff members I encountered during my stay, courtesy was above and beyond thank you all!

Reviewed on Jan 5, 2026

The Historic Magnolia House

The Historic Magnolia House

3.5 out of 5
Price was $875, price is now $682 per person
$682
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
6/10 (2 reviews)
O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $781, price is now $686 per person
$686
per person
Mar 20 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Greensboro (GSO)
9.8/10 Exceptional! (724 reviews)
Green Valley Grill is fantastic, the hotel has charm, love it!

Reviewed on Jan 18, 2026

Greenwood Bed & Breakfast

Greenwood Bed & Breakfast

3 out of 5
Fisher Park
Price was $772, price is now $681 per person
$681
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9.4/10 Exceptional! (52 reviews)
Quiet neighborhood. Nice 120 year old home. Very pleasant and responsive host. Parking directly across the street. Breakfast was delicious and plentiful. Even brought home a couple of freshly picked Japanese Persimmon fruit. Would stay again.

Reviewed on Oct 12, 2025

Dailey Renewal Retreat Bed & Breakfast

Dailey Renewal Retreat Bed & Breakfast

3 out of 5
Lindley Park
Price was $626, price is now $558 per person
$558
per person
Mar 20 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Greensboro (GSO)
9/10 Wonderful! (207 reviews)
This place will always be near and dear to my heart. The breakfast was absolutely delicious, the atmosphere was so cozy and loving I did not want to leave. It was a pleasure to meet Miss Jean Dailey and I hope to come back some time soon. Plus, the house is surrounded by some VERY delicious options for food. If you’re looking for a home-away-from-home getaway, that actually isn’t in the middle of nowhere, I highly recommend!

Reviewed on Aug 5, 2025

Don't see what you're looking for?
See all available trips from Columbus to Winston-Salem
View all trips

Discover the most popular places to visit in Winston-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

Wake Forest University

Take a campus tour or just explore the area of Wake Forest University, during your travels in Winston-Salem. Amble around the area's lush forest or attend a sporting event.

Wake Forest University

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
$80 nightly
The price is $90 total per night from Jan 25 to Jan 26
$90 total
Jan 25 - Jan 26
Total with taxes and fees
8.4/10 Very Good! (1,009 reviews)
Helpful staff,

Reviewed on Jan 5, 2026

Hawthorne Inn and Conference Center
The Historic Brookstown Inn, Trademark Collection by Wyndham

The Historic Brookstown Inn, Trademark Collection by Wyndham

3.5 out of 5
200 Brookstown Ave Winston-Salem NC
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $131 total per night from Feb 8 to Feb 9
$131 total
Feb 8 - Feb 9
Total with taxes and fees
9.4/10 Exceptional! (1,003 reviews)
Large clean rooms and bathrooms. Friendly, helpful staff. Enjoyed wine and cheese bar especially bartender Misty’s polite demeanor.

Reviewed on Jan 19, 2026

The Historic Brookstown Inn, Trademark Collection by Wyndham
La Quinta Inn & Suites by Wyndham Winston-Salem

La Quinta Inn & Suites by Wyndham Winston-Salem

3 out of 5
2020 Griffith Rd Winston-Salem NC
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $82 total per night from Jan 27 to Jan 28
$82 total
Jan 27 - Jan 28
Total with taxes and fees
7.8/10 Good! (29 reviews)
Easy parking, easy check in, could use some updates ! Sad people smoke and it seeps through the vents !

Reviewed on Jan 13, 2026

La Quinta Inn & Suites by Wyndham Winston-Salem
See all 424 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winston-Salem vacation package cost?
Offering great value package deals from $481 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.

Explore a world of travel with Expedia

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