Homestead Vacation Packages

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Your Homestead Vacation

Say goodbye to the hassle of planning and hello to a Homestead vacation package. With the finer details organized before you leave, you can focus on discovering the best of this city, starting with Squirrel Hill South, which is great for cycling, golfing and dining. A trip to Homestead is a great opportunity to take in the sights. Be sure to visit big-name attractions such as Acrisure Stadium, University of Pittsburgh and PNC Park. Expedia can help you escape your daily routine. Tailor your vacation to Homestead to match your travel style, whatever that may look like.

Top Homestead Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Suites Pittsburgh South by IHG

Crowne Plaza Suites Pittsburgh South by IHG

3.5 out of 5
Price was CA $963, price is now CA $896 per person
CA $896
per person
Aug 27 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.8/10 Excellent! (1,005 reviews)
The most unethical front desk in the world and I have traveled the world.

Reviewed on Jul 6, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was CA $1,731, price is now CA $1,492 per person
CA $1,492
per person
Aug 17 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,000 reviews)
It was just ok. Maybe Pittsburgh needs to get a Ritz or Four Seasons.

Reviewed on Jun 24, 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was CA $1,047, price is now CA $960 per person
CA $960
per person
Aug 27 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,543 reviews)
Stayed 3 nights; this hotel does not meet Hilton Curio standards. The issues may be tied to insufficient staffing. Room was not cleaned after the 1st night. We had to go to front desk to get towels and toilet paper, and learned maids are “under a tight schedule.” So because I told maid we wouldn’t be leaving room for 30 minutes, this merited no cleaning? The restaurant was on 2 levels, with the kitchen on the lower level and only the tables on the upper level set. The poor server, who was also the bartender, had to keep getting food downstairs and walking it upstairs to diners. I can’t blame her for the slow service! We found a very cool part of the lobby with a library of interesting books and records to check out, but the front desk never mentioned this. The front desk is not very service-oriented. Don’t stay at this hotel, even if you are going to see a Pirates game.

Reviewed on Jul 6, 2026

The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
Oakland
Price was CA $1,367, price is now CA $1,268 per person
CA $1,268
per person
Aug 17 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
9.2/10 Wonderful! (789 reviews)
I found the property to be excellent in all phases, from cleanliness to staff. A wonderful experience and I will definately stay again when in Pittsburgh.

Reviewed on Jul 1, 2026

Courtyard by Marriott Pittsburgh Downtown

Courtyard by Marriott Pittsburgh Downtown

3 out of 5
Downtown Pittsburgh
Price was CA $1,146, price is now CA $1,072 per person
CA $1,072
per person
Aug 17 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
9/10 Wonderful! (1,003 reviews)
Great location

Reviewed on Jul 6, 2026

Ready to book your vacation to Homestead?

 

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Homestead Hotel Deals

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Jul 9 to Jul 10
CA $190
CA $217 total
Jul 9 - Jul 10
includes taxes & fees
8.2/10 Very good! (3,608 reviews)
"The room was nice, clean. Excellent city view. The bathroom could use an update. Staff was kind and helpful and the valet parking service was great."

Reviewed on Jul 6, 2026

Wyndham Grand Pittsburgh Downtown
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $195 per night from Jul 12 to Jul 13
CA $195
CA $222 total
Jul 12 - Jul 13
includes taxes & fees
9.4/10 Exceptional! (1,931 reviews)
"Room was exceptionally clean and comfortable."

Reviewed on Jul 6, 2026

The Landing Hotel at Rivers Casino
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
1100 Liberty Ave Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Jul 7 to Jul 8
CA $179
CA $204 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (149 reviews)
"Right near the bus terminal so it can get sketchy walking around. Loved the washer and dryer in the room. Heads up to bring unscented detergent if fragrances bother you."

Reviewed on Jul 2, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian
See all 2,020 properties in Homestead
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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Stay near popular Homestead attractions

A cityscape with a river, multiple bridges, and a variety of buildings including skyscrapers.

The Waterfront

9.0/10 (1,071 reviews)
During your visit to Homestead, you can do some window-shopping at The Waterfront. Stroll along the riverfront or attend a sporting event in this family-friendly area.
See properties

What to do in Homestead

Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

CA $79
per adult
Pittsburgh Pirates Baseball Game at PNC Park
Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $41
per adult
90% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
Make new friends as you learn the exciting history of whiskey in Pittsburgh

Whiskey Rebellion & Prohibition Tour

CA $70
per adult
100% of travellers recommend
Whiskey Rebellion & Prohibition Tour
See all activities in Homestead

Frequently asked questions

How much does a Homestead vacation package cost?
Offering excellent value package deals from CA $896 on Expedia, you'll be thrilled with how little a vacation to Homestead costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Homestead?
You can typically find lower rates and better availability in January, February and March. Explore our cheap Homestead vacation packages and you could get some excellent off-season deals.
How many days is enough for Homestead?
To get the most out of your Homestead vacation, we recommend booking for 2 days. Split your time between discovering Sri Venkateswara Temple, Andy Warhol Museum and other must-see attractions, as well as experiencing neighbourhoods like Downtown Pittsburgh and Oakland. If you've got some time to spare, add a day trip to your Homestead vacation itinerary.
Is it worth booking a vacation package to Homestead?
Well known for its shopping and home to leading attractions like Carnegie Museum and Library, a Homestead vacation is sure to leave an impression. Another highlight to check out? Don't miss Bulgarian Macedonian National Educational and Cultural Centre.
How to find the best Homestead package deals?
Begin your search for a Homestead package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Homestead package deal right away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Homestead escape off to a flying start.
Is it cheaper to book a Homestead vacation as a package?
You can enjoy significant savings on your next Homestead escape by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Homestead?
If you've got your Homestead travel dates confirmed, book as early as you can to bag some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Homestead?

  1. Choose when to go: Check your schedule and get packing. Your favourite time of year and the activities on offer will also help you decide when to visit Homestead.
  2. Calculate your budget: Ensure you have enough money to pay for everything from food and transportation to activities and flights. Your hotel will probably be the largest expense during your trip to Homestead.
  3. Decide your trip length: Think about how long you want to spend exploring Homestead. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Homestead vacation package.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.