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Top Romantic vacation packages in Southwest Pennsylvania

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

DoubleTree by Hilton Pittsburgh - Green Tree

￥52,766

per person

Sep 5 - Sep 6

found 6 hours ago

Roundtrip flight included

Chicago (ORD) to Pittsburgh (PIT)

8.6/10 Excellent! (1,095 reviews)

Drury Plaza Hotel Pittsburgh Downtown

Downtown Pittsburgh

￥321,378

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Pittsburgh (PIT)

9.4/10 Exceptional! (2,389 reviews)

Room service was great! Clean comfortable and kind ppl

Reviewed on Aug 2, 2026

Kimpton Hotel Monaco Pittsburgh by IHG

Downtown Pittsburgh

￥70,939

per person

Sep 4 - Sep 5

found 6 hours ago

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

9.4/10 Exceptional! (1,313 reviews)

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

Downtown Pittsburgh

￥59,728

per person

Sep 4 - Sep 5

found 6 hours ago

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

8.2/10 Very Good! (1,098 reviews)

The Atterbury Hotel, Autograph Collection

Downtown Pittsburgh

￥72,502

per person

Sep 4 - Sep 5

found 6 hours ago

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

9/10 Wonderful! (1,010 reviews)

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See all available trips from Chicago to Southwest Pennsylvania

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3 Night Romantic vacations in Southwest Pennsylvania

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

Drury Plaza Hotel Pittsburgh Downtown

Downtown Pittsburgh

￥321,378

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Pittsburgh (PIT)

9.4/10 Exceptional! (2,389 reviews)

Room service was great! Clean comfortable and kind ppl

Reviewed on Aug 2, 2026

Don't see what you're looking for?

See all available trips from Tokyo to Southwest Pennsylvania

View all trips

Top Romantic Southwest Pennsylvania Hotels

Omni William Penn Hotel

530 William Penn Place Pittsburgh PA

15 min walk from PNC Park

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! (2,055 reviews)

"Magical place to stay."

Reviewed on Aug 2, 2026

Mansions on Fifth Hotel

5105 Fifth Avenue Pittsburgh PA

11 min drive from PNC Park

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

8.8/10 Excellent! (1,000 reviews)

Couples like: bar, romance packages available

Travelers say...

"Ask to stay in the main mansion and not the brick coach house. Both buildings are dated."

Reviewed on Jul 30, 2026

The Atterbury Hotel, Autograph Collection

107 6th St Pittsburgh PA

6 min walk from PNC Park

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 ...

See all 3,238 properties in Southwest Pennsylvania

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.