Homestead Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

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.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 13 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
7.6/10 Good! (142 reviews)
Clean and quiet property in downtown Pittsburgh. Had some difficulty leaving the Allied garage because my QR code or the scanner wasn’t working, but otherwise a great stay. Will definitely stay again if I’m in the area.

Reviewed on Jul. 6, 2025

Renaissance Pittsburgh Hotel

Renaissance Pittsburgh Hotel

4 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 13 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
9/10 Wonderful! (1,002 reviews)
Absolutely loved the hotel. The room was very spacious and had a fantastic view. The staff was great. The bar inside the hotel was relaxed and the bartender was awesome. There is so many dining options within walking distance from the hotel. During my stay they was doing the Picklesburgh Festival, and this did not impact my stay at all. It was a great stay, planning to do it again soon.

Reviewed on Jul. 11, 2025

TRYP by Wyndham Pittsburgh/Lawrenceville

TRYP by Wyndham Pittsburgh/Lawrenceville

3 out of 5
Lawrenceville
per person
Sep 19 - Sep 22
found 13 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
8.6/10 Excellent! (819 reviews)
The room was not very clean

Reviewed on Jul. 7, 2025

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
per person
Sep 19 - Sep 22
found 13 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
8.2/10 Very Good! (1,003 reviews)
Staff was great!! A+

Reviewed on Jul. 1, 2025

The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
North Side
per person
Sep 19 - Sep 22
found 13 hours ago
Roundtrip flight included
Calgary (YYC) to Pittsburgh (PIT)
9.4/10 Exceptional! (803 reviews)
Did not like parking and having to walk far

Reviewed on Jul. 10, 2025

Ready to book your vacation to Homestead?

 

Choose your dates

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 $170 per night from Jul 16 to Jul 17
CA $170
CA $194 total
Jul 16 - Jul 17
includes taxes & fees
8/10 Very Good! (2,881 reviews)
"The hotel was nice and clean and a short walking distance to the park and baseball stadium."

Reviewed on Jul. 8, 2025

Wyndham Grand Pittsburgh Downtown
Omni William Penn Hotel
Omni William Penn Hotel
4 out of 5
530 William Penn Place, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from Jul 27 to Jul 28
CA $196
CA $224 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,530 reviews)
"It was a very cool experience staying at this historic hotel. It's in a great area. The lobby is stunning. The room we stayed in was spacious but nothing fancy. Our bed was very uncomfortable - it caved into the middle. The friendly staff gave offered us a breakfast credit for the bad sleep. Overall ..."

Reviewed on Jul. 9, 2025

Omni William Penn Hotel
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Joinery Hotel Pittsburgh, Curio Collection by Hilton
4 out of 5
453 Boulevard of the Allies, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Jul 16 to Jul 17
CA $173
CA $198 total
Jul 16 - Jul 17
includes taxes & fees
8.2/10 Very Good! (1,323 reviews)
"Friendly and clean"

Reviewed on Jul. 10, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,798 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Homestead

PNC Park which includes a city

PNC Park

4.5/5(67 reviews)

Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.

PNC Park
University of Pittsburgh

University of Pittsburgh

4.5/5(36 reviews)

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

University of Pittsburgh
Carnegie Mellon University

Carnegie Mellon University

4.5/5(21 reviews)

Walk around the campus of Carnegie Mellon University, a top college in Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Carnegie Mellon University

What to do in Homestead

Visit beautiful shopping and dining complex in your private tour

Private City Kickstart Tour: Tokyo

CA $185
per adult
100% of travellers recommend
Private City Kickstart Tour: Tokyo
JUST THE TOUR - An open top Double Decker Bus Sightseeing Tour of Pittsburgh.

JUST THE TOUR - Double Decker bus sightseeing tour of Pittsburgh.

CA $62
per adult
94% of travellers recommend
JUST THE TOUR - Double Decker bus sightseeing tour of Pittsburgh.
Happy hour cruiser

2 Hour Private Sightseeing Charter Boat Cruise

CA $529
per traveller
2 Hour Private Sightseeing Charter Boat Cruise
See all activities in Homestead

Frequently asked questions

How much does a Homestead vacation package cost?
Offering excellent value package deals from CA $807 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.

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