Pittsburgh Romantic Vacations 2026

Top Romantic vacation packages in Pittsburgh

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

DoubleTree by Hilton Pittsburgh - Green Tree

$306

per person

Dec 11 - Dec 14

found 3 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Pittsburgh (PIT)

8.8/10 Excellent! (1,236 reviews)

The Inn on Negley

Shadyside

$640

per person

Dec 12 - Dec 15

just found

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

10/10 Exceptional! (225 reviews)

This Inn is beautiful, perfectly located within a couple minutes of downtown, very well maintained, breakfast was wonderful, the room was super comfortable with quality linens and a very comfortable batch. Wonderful staff as well, Peter gave us some history of Pittsburgh and some ideas to make our trip back home even better! We plan on coming back to Pittsburgh and staying here again.

Reviewed on Sep 30, 2026

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

$586

per person

Dec 11 - Dec 14

found 3 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Pittsburgh (PIT)

8.6/10 Excellent! (1,001 reviews)

DoubleTree by Hilton Pittsburgh - Cranberry

$641

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Midland (MAF) to Pittsburgh (PIT)

8.8/10 Excellent! (1,000 reviews)

Fairmont Pittsburgh

Downtown Pittsburgh

$631

per person

Nov 6 - Nov 8

found 6 hours ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

8.8/10 Excellent! (1,001 reviews)

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3 Night Romantic vacations in Pittsburgh

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

DoubleTree by Hilton Pittsburgh - Green Tree

$306

per person

Dec 11 - Dec 14

found 3 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Pittsburgh (PIT)

8.8/10 Excellent! (1,236 reviews)

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

Save 100% on your flight

$472

per person

Nov 6 - Nov 9

found 8 hours ago

Roundtrip flight included

Myrtle Beach (MYR) to Pittsburgh (PIT)

8.6/10 Excellent! (1,001 reviews)

The Inn on Negley

Shadyside

$640

per person

Dec 12 - Dec 15

just found

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

10/10 Exceptional! (225 reviews)

Reviewed on Sep 30, 2026

Don't see what you're looking for?

See all available trips from Columbus to Pittsburgh

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4 Night Romantic vacations in Pittsburgh

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

Fairmont Pittsburgh

Downtown Pittsburgh

$730

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Greenville (GSP) to Pittsburgh (PIT)

8.8/10 Excellent! (1,001 reviews)

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

$781

per person

Dec 19 - Dec 23

found 1 day ago

Roundtrip flight included

Miami (MIA) to Pittsburgh (PIT)

8.6/10 Excellent! (1,001 reviews)

The Inn on Negley

Shadyside

$1,006

per person

Dec 17 - Dec 21

found 6 hours ago

Roundtrip flight included

Phoenix (PHX) to Pittsburgh (PIT)

10/10 Exceptional! (225 reviews)

Reviewed on Sep 30, 2026

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How can I find the best Pittsburgh 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 Pittsburgh 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 Pittsburgh?

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 Pittsburgh?

Put a price on love with stunning deals for duos starting at just $306. 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 Pittsburgh 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 Pittsburgh?

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 Pittsburgh?

To book a loved-up break in Pittsburgh, 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 Pittsburgh 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 Pittsburgh 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 Pittsburgh Hotels

Omni William Penn Hotel

530 William Penn Place Pittsburgh PA

25 min walk from Acrisure Stadium

You and your sweetheart are sure to love the in-room massages and 3 restaurants at this upscale hotel. You'll also appreciate the luxury bedding, 2 bars, and ...

9.2/10 Wonderful! (1,992 reviews)

"We had a great hotel stay. The hotel is beautiful and the staff are welcoming. We loved the location . The Fitness room was amazing"

Reviewed on Oct 5, 2026

Mansions on Fifth Hotel

5105 Fifth Avenue Pittsburgh PA

12 min drive from Acrisure Stadium

Ready for a romantic getaway? Consider this Edwardian hotel, featuring hydromassage showers, a lobby fireplace, and romance packages. Couples will appreciate ...

The Atterbury Hotel, Autograph Collection

107 6th St Pittsburgh PA

17 min walk from Acrisure Stadium

Unwind and make time for a romantic getaway at this historic hotel, featuring premium mattresses and onsite dining. Couples will love the luxury bedding and ...

9/10 Wonderful! (1,005 reviews)

"Been staying here for years.... Never had a bad stay."

Reviewed on Oct 6, 2026

See all 2,046 properties in Pittsburgh

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.