South Side Romantic Vacations 2026

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4 Night Romantic vacations in South Side

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

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

South Side Flats

$727

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Sacramento (SMF) to Pittsburgh (PIT)

8/10 Very Good! (1,014 reviews)

My daughter and I were in town for the Olivia Rodrigo concert and arrived a bit early and we were told our room would be ready by 3. The front desk staff was going through a shift change but they were very attentive and pleasant. Our room was clean, modern and very nice. Shower was large and clean. Breakfast was included and a pleasant surprise. Thank you.

Reviewed on Oct 1, 2026

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How can I find the best South Side 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 South Side 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 South Side?

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 South Side?

Put a price on love with stunning deals for duos starting at just $727. Prices and availability are subject to change. Additional terms may apply.

Can I book South Side spa packages for couples?

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How can I book romantic weekend getaway packages in South Side?

To book a loved-up break in South Side, 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 South Side 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 South Side 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 South Side Hotels

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

20 S 10th St Pittsburgh PA

9 min walk from Rex Theater

A lobby fireplace, luxury bedding, and more await visiting couples at this romantic hotel.

8/10 Very Good! (1,023 reviews)

"My daughter and I were in town for the Olivia Rodrigo concert and arrived a bit early and we were told our room would be ready by 3. The front desk staff was going through a shift change but they were very attentive and pleasant. Our room was clean, modern and very nice. Shower was large and clean. ..."

Reviewed on Oct 1, 2026

See all 2,018 properties in South Side

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.