Winston - Salem Romantic Vacations 2026

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Top Romantic vacation packages in Winston - Salem

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

Kimpton Cardinal Hotel by IHG

$683

per person

Oct 9 - Oct 11

found 7 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Greensboro (GSO)

9/10 Wonderful! (1,000 reviews)

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4 Night Romantic vacations in Winston - Salem

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

Red Roof Inn Winston-Salem

$411

per person

Oct 8 - Oct 12

found 13 hours ago

Roundtrip flight included

Chicago (CHI) to Greensboro (GSO)

5.8/10 (554 reviews)

Scary property, people begging for money in the parking lot, drug deals going on. People looking in our car windows. Left and went to another hotel in the area. Did not feel safe at all.

Reviewed on Aug 23, 2026

Winston-Salem Marriott

$684

per person

Oct 8 - Oct 12

found 13 hours ago

Roundtrip flight included

Chicago (CHI) to Greensboro (GSO)

8.6/10 Excellent! (753 reviews)

The Historic Brookstown Inn, Trademark Collection by Wyndham

$714

per person

Oct 8 - Oct 12

found 13 hours ago

Roundtrip flight included

Chicago (CHI) to Greensboro (GSO)

9.6/10 Exceptional! (1,006 reviews)

I didn’t use a lot of the amenities. But the staff were great. It’s in a good location for Old Salem.

Reviewed on Aug 28, 2026

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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 and visiting outside busy months of .

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 $411. Stay during the quiet season, in , for breaks to make your bank balance smile. 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.

What’s the best time of year for a romantic vacation in Winston - Salem?

Book your romantic getaway during the quieter months of when you can have the place to yourself, pretty much. To show your partner off to the world, provide a more abundant audience.

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?

Top Romantic Winston - Salem Hotels

DoubleTree by Hilton Winston Salem - University

5790 University Pkwy Winston-Salem NC

8 min drive from Wake Forest University

Book a stay at this romantic hotel, featuring premium mattresses and onsite dining. Couples will appreciate the Egyptian cotton sheets, terrace, and outdoor ...

The Historic Brookstown Inn, Trademark Collection by Wyndham

200 Brookstown Ave Winston-Salem NC

7 min drive from Wake Forest University

If you're in the mood for love, consider a stay at this romantic hotel, featuring a garden and romance packages. You'll also love the luxury bedding and ...

9.6/10 Exceptional! (1,004 reviews)

"I didn’t use a lot of the amenities. But the staff were great. It’s in a good location for Old Salem."

Reviewed on Aug 28, 2026

La Quinta Inn & Suites by Wyndham Winston-Salem

2020 Griffith Rd Winston-Salem NC

12 min drive from Wake Forest University

If you're looking for a special getaway, consider a stay at this romantic hotel where there's premium mattresses and much more for you and your partner to ...

See all 603 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.