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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.
  • Exclusive Cottage | Living area
    Sep 25 - Sep 27

    Excelsior at the Manor House + Flight

    Clemmons
    2 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 • Chicago (CHI) - Greensboro (GSO)
    RFD - GSO • 1 stop GSO - ORD • Nonstop
    $439
    $425
    per traveler
    found 19 hours ago
    Excelsior at the Manor House
  • Lobby sitting area
    Oct 9 - Oct 11

    Hawthorne Inn and Conference Center + Flight

    Winston-Salem
    2 nights
    3.0 star property
    8.6/10 - Excellent (1,169 reviews)
    "The breakfast charge was 10$ for hot breakfast of scrambled eggs and sausage. You had to have a ticket to get into the breakfast room which you had to buy at the front desk, slow front desk, annoying."
    Reviewed August 1, 2026
    Roundtrip • Chicago (CHI) - Greensboro (GSO)
    ORD - GSO • Nonstop GSO - ORD • Nonstop
    $494
    $456
    per traveler
    found 1 day ago
    Hawthorne Inn and Conference Center
  • Restaurant
    Sep 25 - Sep 27

    The Shaffner Inn + Flight

    Winston-Salem
    2 nights
    2.0 star property
    9.2/10 - Wonderful (230 reviews)
    "The Reynaldo Room was very loud. Heavy street noise & loud music from cars. If you’re a light sleeper this room isn’t great."
    Reviewed July 31, 2026
    Roundtrip • Chicago (CHI) - Greensboro (GSO)
    RFD - GSO • 1 stop GSO - ORD • Nonstop
    $617
    $588
    per traveler
    found 19 hours ago
    The Shaffner Inn
  • Porch
    Oct 9 - Oct 11

    Summit Street Inns + Flight

    Winston-Salem
    2 nights
    3.5 star property
    9.8/10 - Exceptional (277 reviews)
    Roundtrip • Chicago (CHI) - Greensboro (GSO)
    ORD - GSO • Nonstop GSO - ORD • Nonstop
    $640
    $613
    per traveler
    found 1 day ago
    Summit Street Inns
  • Lobby
    Sep 25 - Sep 27

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

    Clemmons
    2 nights
    3.0 star property
    8.4/10 - Very Good (1,001 reviews)
    Roundtrip • Chicago (CHI) - Greensboro (GSO)
    RFD - GSO • 1 stop GSO - ORD • Nonstop
    $467
    $451
    per traveler
    found 19 hours ago
    Village Inn Clemmons/Winston Salem, Trademark by Wyndham

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

Exterior

Courtyard by Marriott Winston-Salem Hanes Mall

Courtyard by Marriott Winston-Salem Hanes Mall
3.0 star property
4.3 mi from Winston - Salem
8.4 out of 10, Very Good, (779 reviews)
$79 nightly
The price is $89
Aug 6 - Aug 7
Total with taxes and fees
Courtyard by Marriott Winston-Salem Hanes Mall
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 $425. 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?