Upper Hill Vacation Packages 2026 from $731

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The Latest Upper Hill Vacation Packages

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

Oct 28 - Nov 1
EVEN Hotel Pittsburgh Downtown by IHG + Flight
Downtown Pittsburgh
4 nights
4.0 star property
8.8/10 - Excellent (1,099 reviews)
"Ice machine was not working on our fifth floor room; fortunately, merely a few extra minutes on elevator to floor six for ice."
Reviewed July 30, 2026
Roundtrip • Atlanta (ATL) - Pittsburgh (PIT)
ATL - PIT • Nonstop PIT - ATL • 1 stop
~~$967~~
$731
per traveler
found 17 hours ago
EVEN Hotel Pittsburgh Downtown by IHG
Oct 8 - Oct 11
Stay Pittsburgh + Flight
Downtown Pittsburgh
3 nights
2.0 star property
8.0/10 - Very Good (314 reviews)
"Very responsive, great location, awesome hosts! 10/10 would recommend."
Reviewed July 31, 2026
Roundtrip • Boston (BOS) - Pittsburgh (PIT)
BOS - PIT • Nonstop PIT - BOS • 1 stop
Save 100% on your flight
~~$1,173~~
$784
per traveler
found 1 day ago
Stay Pittsburgh
Oct 28 - Nov 1
Joinery Hotel Pittsburgh, Curio Collection by Hilton + Flight
Downtown Pittsburgh
4 nights
4.0 star property
8.6/10 - Excellent (1,600 reviews)
"The room was clean and a good size for a single traveler. Check-in was a bit hectic with computer issues so I did not get confirmation on my valet. The associate who took care of me did not speak loud enough for me to hear her but I think she lacked a bit of customer service skills. She did not seem confident under the circumstances. I had booked 2 rooms through a third party so I was not thrilled when I found out I was the only person on the 10th floor. With that being said, I did call the..."
Reviewed August 3, 2026
Roundtrip • Atlanta (ATL) - Pittsburgh (PIT)
ATL - PIT • Nonstop PIT - ATL • 1 stop
~~$1,009~~
$759
per traveler
found 17 hours ago
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Oct 16 - Oct 18
The Westin Pittsburgh, a Marriott Hotel + Flight
Downtown Pittsburgh
2 nights
4.0 star property
8.6/10 - Excellent (1,001 reviews)
"The staff at the Westin was extremely helpful and proactive. The initial room they gave us had some issues, including a smoke-like smell (not cigarette smoke). As soon as we notified reception, someone handled it extremely professionally, and within minutes we were moved to a much better room."
Reviewed August 3, 2026
Roundtrip • Boston (BOS) - Pittsburgh (PIT)
BOS - PIT • Nonstop PIT - BOS • Nonstop
~~$1,261~~
$964
per traveler
found 1 day ago
The Westin Pittsburgh, a Marriott Hotel
Sep 15 - Sep 20
The Landing Hotel at Rivers Casino + Flight
North Side
5 nights
2.0 star property
9.4/10 - Exceptional (2,101 reviews)
"Clean spacious room, attached to casino for easy access. No complaints."
Reviewed August 3, 2026
Roundtrip • Atlanta (ATL) - Pittsburgh (PIT)
ATL - PIT • 1 stop PIT - ATL • 1 stop
Save 100% on your flight
~~$1,201~~
$931
per traveler
found 1 day ago
The Landing Hotel at Rivers Casino