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Photo by Visit Winston Salem
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Winston - Salem Romantic Vacations

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Top Romantic vacation packages in Winston - Salem

Price found within the past 48 hours. Click for updated prices.
  • Lobby sitting area
    Aug 27 - Aug 30

    Hawthorne Inn and Conference Center + Flight

    Winston-Salem
    3 nights
    3.0 star property
    8.6/10 - Excellent (1,176 reviews)
    "I had an excellent stay here at the Hawthorne. I highly recommend"
    Reviewed July 27, 2026
    Roundtrip • New York (JFK) - Greensboro (GSO)
    JFK - GSO • 1 stop GSO - JFK • 1 stop
    $562
    $531
    per traveler
    found 9 hours ago
    Hawthorne Inn and Conference Center
  • Restaurant
    Aug 27 - Aug 30

    The Shaffner Inn + Flight

    Winston-Salem
    3 nights
    2.0 star property
    9.2/10 - Wonderful (229 reviews)
    "We were on town for the Bowman Gray race. The inn keeper was great. The room was beautiful and the bed was great. The continual breakfast had eggs, sausage, bacon fruit,etc. Fresh orange juice. Definitely would return"
    Reviewed July 26, 2026
    Roundtrip • New York (JFK) - Greensboro (GSO)
    JFK - GSO • 1 stop GSO - JFK • 1 stop
    $756
    $658
    per traveler
    found 9 hours ago
    The Shaffner Inn
  • Lobby
    Aug 27 - Aug 30

    Village Inn Clemmons/Winston Salem, Trademark by Wyndham + Flight

    Clemmons
    3 nights
    3.0 star property
    8.4/10 - Very Good (1,002 reviews)
    Roundtrip • New York (JFK) - Greensboro (GSO)
    JFK - GSO • 1 stop GSO - JFK • 1 stop
    $599
    $564
    per traveler
    found 9 hours ago
    Village Inn Clemmons/Winston Salem, Trademark by Wyndham
  • Exclusive Cottage | Living area
    Aug 27 - Aug 30

    Excelsior at the Manor House + Flight

    Clemmons
    3 nights
    3.5 star property
    8.4/10 - Very Good (86 reviews)
    "Lovely place, great for traveling with kids. We were passing through so didn’t have time to check out the various amenities sadly, but if we’re able we’ll definitely come back and spend more time"
    Reviewed June 19, 2026
    Roundtrip • New York (JFK) - Greensboro (GSO)
    JFK - GSO • 1 stop GSO - JFK • 1 stop
    $628
    $610
    per traveler
    found 9 hours ago
    Excelsior at the Manor House
  • Porch
    Aug 27 - Aug 30

    Summit Street Inns + Flight

    Winston-Salem
    3 nights
    3.5 star property
    9.8/10 - Exceptional (276 reviews)
    "This is probably one of the best places I have stayed at in many years. Lots of dining options in walking distance, safe off street parking, unique rooms with attention to details in decor and a very yummy breakfast. I will be back."
    Reviewed July 24, 2026
    Roundtrip • New York (JFK) - Greensboro (GSO)
    JFK - GSO • 1 stop GSO - JFK • 1 stop
    $796
    $781
    per traveler
    found 9 hours ago
    Summit Street Inns

Discover the most popular places to visit in Winston - Salem

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.

What to do in Winston - Salem

Winston-Salem True Crime Tour

Winston-Salem True Crime Tour

$19
per adult
0% of travelers recommend
Winston-Salem True Crime Tour
See all activities in Winston - Salem

Top Romantic Winston - Salem Hotels

Courtyard

The Historic Brookstown Inn, Trademark Collection by Wyndham

The Historic Brookstown Inn, Trademark Collection by Wyndham
3.5 star property
0.6 mi from Winston - Salem
9.6 out of 10, Exceptional, (1,003 reviews)
$140 nightly
The price is $158
Aug 9 - Aug 10
Total with taxes and fees
The Historic Brookstown Inn, Trademark Collection by Wyndham
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.
See all properties in Winston - Salem

How to find a romantic Winston - Salem vacation

How can I find the best Winston - Salem vacation packages for couples?

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Winston - Salem romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Winston - Salem?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Winston - Salem?

Put a price on love with stunning deals for duos starting at just $531. Prices and availability are subject to change. Additional terms may apply.

Can I book Winston - Salem spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Winston - Salem?

To book a loved-up break in Winston - Salem, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

Can I book a romantic trip to Winston - Salem with free cancellation and/or flexible dates?

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Winston - Salem romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?