A calm lake with a central island, surrounded by a dense forest and a stone bridge.

Luxury Hotels & Resorts in Highland Park from AU$158

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Our top choices for Highland Park luxury hotels

A large stone building with a central entrance, multiple windows, and a symmetrical facade.

1. Mansions on Fifth Hotel

Mansions on Fifth Hotel
4.0 star property
Shadyside
8.8 out of 10, Excellent, (1,011 reviews)
  • cleanliness
    Restored Edwardian mansion offers opulent elegance with premium beds, hydromassage showers, and designer toiletries in Shadyside.
The price is AU$217
includes taxes & fees
4 Oct - 5 Oct
Mansions on Fifth Hotel
A spacious lobby with a high ceiling, a large cityscape mural, and a seating area with a railing.

2. Drury Plaza Hotel Pittsburgh Downtown

Drury Plaza Hotel Pittsburgh Downtown
4.0 star property
Downtown Pittsburgh
9.4 out of 10, Exceptional, (2,372 reviews)
  • cleanliness
    Pittsburgh sanctuary offers historical sophistication with rooftop views, indoor pool, and spa pool.
The price is AU$207
includes taxes & fees
18 Oct - 19 Oct
Drury Plaza Hotel Pittsburgh Downtown
A white building with a porch, a sign for The Inn on Negley, and a brick staircase leading up to the entrance.

3. The Inn on Negley

The Inn on Negley
4.0 star property
Shadyside
10.0 out of 10, Exceptional, (225 reviews)
The price is AU$427
includes taxes & fees
5 Oct - 6 Oct
The Inn on Negley
A modern bar area with a marble countertop, bar stools, and a bookshelf filled with books and decorative items.

4. The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection
4.5 star property
Oakland
9.2 out of 10, Wonderful, (834 reviews)
  • cleanliness
    Rooftop terrace luxury meets university charm at this Oakland hotel with upscale dining and modern comforts.
The price is AU$394
includes taxes & fees
25 Oct - 26 Oct
The Oaklander Hotel, Autograph Collection
A rooftop terrace with outdoor seating, a city skyline view, and a clear sky.

5. Comfort Inn & Suites Pittsburgh-Northshore

Comfort Inn & Suites Pittsburgh-Northshore
4.0 star property
North Side
7.6 out of 10, Good, (620 reviews)
The price is AU$159
includes taxes & fees
14 Oct - 15 Oct
Comfort Inn & Suites Pittsburgh-Northshore
A hotel with a modern facade, illuminated signage, and a covered entrance.

6. DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
4.0 star property
Downtown Pittsburgh
8.4 out of 10, Very good, (1,112 reviews)
The price is AU$238
includes taxes & fees
21 Oct - 22 Oct
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
A grand lobby with a grand piano, plush seating, chandeliers, and ornate decor.

7. Omni William Penn Hotel

Omni William Penn Hotel
4.0 star property
Downtown Pittsburgh
9.2 out of 10, Wonderful, (1,980 reviews)
  • cleanliness
    Historic elegance meets modern luxury in this Pittsburgh gem, with opulent rooms and 3 restaurants.
The price is AU$355
includes taxes & fees
25 Oct - 26 Oct
Omni William Penn Hotel
A spacious lobby with a high ceiling, a central seating area, and a staircase leading to upper floors.

8. EVEN Hotel Pittsburgh Downtown by IHG

EVEN Hotel Pittsburgh Downtown by IHG
4.0 star property
Downtown Pittsburgh
8.8 out of 10, Excellent, (1,055 reviews)
The price is AU$212
includes taxes & fees
19 Oct - 20 Oct
EVEN Hotel Pittsburgh Downtown by IHG
A rooftop lounge with seating and a view of the cityscape at dusk.

9. Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton
4.0 star property
Downtown Pittsburgh
8.6 out of 10, Excellent, (1,661 reviews)
  • cleanliness
    Boutique luxury in city centre Pittsburgh offers pillowtop beds, designer toiletries, and record players.
The price is AU$214
includes taxes & fees
18 Oct - 19 Oct
Joinery Hotel Pittsburgh, Curio Collection by Hilton
The entrance of the Hotel Monaco with a grand facade, a receptionist at the entrance, and a statue of a dog on the right.

10. Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG
4.5 star property
Downtown Pittsburgh
9.4 out of 10, Exceptional, (1,320 reviews)
  • cleanliness
    Indulge in city centre luxury with pillowtop beds and evening receptions at this stylish Pittsburgh retreat.
The price is AU$372
includes taxes & fees
18 Oct - 19 Oct
Kimpton Hotel Monaco Pittsburgh by IHG
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.
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Top Highland Park Hotel Reviews

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

8/10 Good
"The room we stayed in was older and not very bright. It was clean but which we would have had a renovated room. Housekeeping was amazing and very nice."
BARBARA 4-night trip
Posted 1 hour ago
Wyndham Grand Pittsburgh Downtown

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Highland Park?
Expedia can help you arrange a flight to Pittsburgh International Airport (PIT) airport or Latrobe, PA (LBE-Arnold Palmer Regional) airport, and then you can select from various places to stay that will deliver the luxury you'd like to find. Amenities are important when you plan a holiday, so we make it easy to get what you need to make your stay relaxing and comfortable. If you want an upscale hotel that has fine dining, a spa or several swimming pools, Expedia can help you find the best luxury hotel experience that Highland Park has to offer. Highland Park has some interesting things to see and do including Three Rivers Heritage Trail, so you might want to take in the local sights during your visit.
What's there to see and do in Highland Park?
Enjoy Highland Park with a stop at Three Rivers Heritage Trail, PPG Paints Arena and PNC Park. If you have extra time while you're in the area, you might want to see Acrisure Stadium and Bakery Square.

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