Winston - Salem Vacations from $660

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The Latest Winston - Salem vacation packages

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

Julian Price House

Fisher Park
$660
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
10/10 Exceptional! (164 reviews)
Gorgeous and comfortable, I really enjoy staying here.

Reviewed on Oct 20, 2026

Proximity Hotel

Proximity Hotel

$1,326
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9.8/10 Exceptional! (1,001 reviews)
Our room was clean and nice. Friendly staff as well!

Reviewed on Oct 11, 2026

O.Henry Hotel

O.Henry Hotel

$1,478
per person
Dec 22 - Dec 28
found 7 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Greensboro (GSO)
9.8/10 Exceptional! (879 reviews)
La Quinta Inn & Suites by Wyndham Greensboro Arpt High Point

La Quinta Inn & Suites by Wyndham Greensboro Arpt High Point

$727
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
8.6/10 Excellent! (1,006 reviews)
I like the location and the proximity of the hotel to the airport and UNC Greensboro. I will most likely return for another stay at this hotel in the future.

Reviewed on Oct 18, 2026

StudioRes by Marriott Greensboro Airport

StudioRes by Marriott Greensboro Airport

$884
per person
Dec 22 - Dec 28
found 7 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Greensboro (GSO)
9.2/10 Wonderful! (65 reviews)
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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

8.6/10 (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.
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A large stadium with tiered seating and a grassy field.
Photo by Melanie E

Bowman Gray Stadium

8.4/10 (7 reviews)
Known as "The Madhouse," this quarter-mile NASCAR track delivers heart-pounding short track racing and football games. Arrive early for prime general admission seating and bring a small cooler for the full experience.
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A cluster of orchids with patterned petals and a pink center.
Photo by Cynthia Phillips

Reynolda Gardens

9.0/10 (139 reviews)
Explore the formal gardens and historic 1913 greenhouse at this serene botanical haven once part of the Reynolda Estate. The free admission gardens showcase vibrant seasonal blooms along tranquil walking paths.
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Benton Convention Center

8.2/10 (241 reviews)
The Benton Convention Center showcases Winston-Salem's arts and industrial heritage through local artwork and thoughtful design. Its flexible space connects to downtown via skywalks from the Cherry Street parking deck.
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Hanes Mall

8.4/10 (1,145 reviews)
Winston-Salem's premier shopping destination houses over 200 retailers across two spacious levels. Explore flagship stores like Belk and Dillard's, then recharge at the diverse food court during your retail adventure.
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Lawrence Joel Veterans Memorial Coliseum

8.0/10 (281 reviews)
The Lawrence Joel Veterans Memorial Coliseum honors a local Medal of Honor recipient while hosting Wake Forest basketball games. Experience the electric atmosphere or catch diverse events held here.
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Truist Stadium

8.4/10 (363 reviews)
This modern stadium delivers intimate Minor League Baseball action as the Winston-Salem Dash's home field. Enjoy craft beers at the Foothills Brewing Flight Deck while watching future MLB stars under evening lights.
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Truist Sports Park

10.0/10 (1 review)
This premier multi-sport complex features 15 well-maintained fields, including 11 natural grass and 4 turf surfaces. Watch evening games under the lights or enjoy the stadium's elevated viewing areas during tournaments.
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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

420 High St Winston-Salem NC
Fully refundableReserve now, pay when you stay
$68 nightly
$76 total
Oct 25 - Oct 26
Total with taxes and fees
Hawthorne Inn and Conference Center
Suburban Studios Winston Salem-University Parkway

Suburban Studios Winston Salem-University Parkway

7910 N Point Blvd Winston-Salem NC
$55 nightly
$62 total
Nov 22 - Nov 23
Total with taxes and fees
6.2/10 (1,001 reviews)
"Only for one night stay. It is your very basic. The beds need some update."

Reviewed on Oct 22, 2026

Suburban Studios Winston Salem-University Parkway
La Quinta Inn & Suites by Wyndham Winston-Salem

La Quinta Inn & Suites by Wyndham Winston-Salem

2020 Griffith Rd Winston-Salem NC
Fully refundableReserve now, pay when you stay
$83 nightly
$94 total
Nov 18 - Nov 19
Total with taxes and fees
7.4/10 Good! (293 reviews)
"Nice place to stay, breakfast is not that bad. Continental breakfast so you know what to expect."

Reviewed on Oct 22, 2026

La Quinta Inn & Suites by Wyndham Winston-Salem
See all 604 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)

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Frequently asked questions

How much does a Winston - Salem vacation package cost?
Vacation packages in Winston - Salem are centered on Winston-Salem. A weekend trip there typically costs around $800 per adult, with prices ranging from around $500 to $1,500 per adult.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How can I save money on a Winston - Salem vacation package?
When you bundle, you can save up to 30%*. To save money on a Winston - Salem package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's included in a Winston - Salem vacation package?
A Winston - Salem vacation package in Winston-Salem lets you combine flights, hotel stays, and rental cars. Many hotels offer free breakfast, and some provide airport shuttle service to and from Raleigh - Durham Intl. Airport (RDU).Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How do I find cheap Winston - Salem vacation package deals?
Lower-priced Winston - Salem vacation packages are available in Winston-Salem, where prices start around $470 per adult for weekend trips. Package prices in February average around $750 per adult for a 2-day trip.Bundling your flight and hotel can offer additional savings compared with booking separately. Weekend Winston-Salem packages typically save around $15 per adult, while week-long packages save around $50 per adult.Browse cheap vacation packages in Winston - Salem on Expedia to compare current deals for Winston-Salem and your travel dates.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
What is the best time to visit Winston - Salem?
The best time for a Winston - Salem vacation package in Winston-Salem city is during September and October, when the weather is pleasant with average highs around 82°F in September and 71°F in October. April is also a busy month for visitors. Conditions may differ elsewhere in the wider Winston - Salem region.If you prefer a quieter trip with fewer crowds, consider visiting in December, when average highs are around 51°F.
What types of vacation packages are available in Winston - Salem?
Winston - Salem vacation packages, concentrated in the city of Winston-Salem, come in several styles to match different travel preferences:
  • Budget: For value-conscious travelers, properties like Sleep Inn Hanes Mall, rated 7.6 out of 10 by travelers, offer amenities such as free breakfast and free WiFi.
  • Pet-friendly: Travelers with pets can consider options like Spark by Hilton Winston-Salem University, rated 8.3 out of 10 by travelers, which provides pet-friendly accommodations and free breakfast.
  • Breakfast included: Many packages feature hotels that include breakfast, such as Summit Street Inns, a 3.5-star property rated 9.4 out of 10 by travelers, known for its fabulous breakfast.
  • Parking: Hotels with convenient parking are available, including Fairfield Inn & Suites by Marriott Winston-Salem Hanes Mall, rated 8.8 out of 10 by travelers, which also offers free breakfast and an outdoor pool.
  • Family: For those traveling with family, Hilton Garden Inn Winston-Salem/Hanes Mall, rated 8.3 out of 10 by travelers, provides family rooms, a restaurant, and free breakfast, making it a comfortable base.
Which destinations should I consider for a Winston - Salem vacation?
When planning a Winston - Salem vacation, several cities in the region offer distinct experiences and lodging options:
  • Winston-Salem: This is the primary urban lodging base, ideal for travelers seeking city attractions, family-friendly activities, outdoor pursuits, and business travel. It offers the most hotel choices in the region.
  • Kernersville: For a family-friendly trip with a focus on outdoor activities and scenic views, Kernersville provides a good range of lodging.
  • Mocksville: Couples looking for a romantic getaway with access to outdoor activities and scenic views will find Mocksville a suitable base.
  • King: This area is also well-suited for romantic getaways, offering outdoor activities and adventure, making it a good choice for those seeking a more active escape.
Is Winston - Salem better suited for a beach vacation or a cultural trip?
Winston - Salem is primarily an urban and outdoor destination, with a strong focus on city attractions and natural landscapes. The region, particularly Winston-Salem city, provides a rich cultural experience alongside its outdoor appeal.For those interested in history and heritage, Winston-Salem city is home to Old Salem, a historic district with preserved 18th and 19th-century buildings. Travelers seeking outdoor activities can explore places like Hanging Rock State Park, known for its scenic trails and rock formations. A Winston - Salem vacation package can be customized around these diverse activities.
Which airport should I use for a Winston - Salem vacation?
For a Winston - Salem vacation, Raleigh - Durham International Airport (RDU) and Charlotte-Douglas International Airport (CLT) are major hubs that serve the wider region. Piedmont Triad International Airport (GSO) in Greensboro is also a convenient option, offering closer proximity to the Winston - Salem area.
What are the top things to do in Winston - Salem?
A Winston - Salem vacation is best explored from a base in Winston-Salem city, which offers a mix of urban attractions and easy access to outdoor activities:Browse and book things to do in Winston - Salem on Expedia.
What is the best time to book a Winston - Salem vacation package?
Book your Winston - Salem vacation package around 3 weeks in advance, with packages located in Winston-Salem. It gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 1 and 6 weeks out.May, August, and October are the most popular months for Winston - Salem packages in Winston-Salem, so booking earlier is advisable if you're traveling during those months.
How many days do you need for a Winston - Salem vacation?
Most Winston - Salem vacation packages last around 2 days, with stays in Winston-Salem, a city known for its urban attractions, family-friendly sites, and outdoor activities. Most travelers choose weekend trips, giving you time to explore historic sites like Old Salem, while some opt for week-long stays to experience more of the area.
Can I change or cancel my Winston - Salem vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Winston - Salem vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Winston - Salem vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Winston - Salem vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Winston - Salem?
To find last-minute vacation packages to Winston - Salem, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Winston - Salem vacation packages?
Free cancellation on a Winston - Salem vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Winston - Salem vacation as a package or separately?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Winston - Salem getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Winston - Salem vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.