Windsor Heights Vacation Packages

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Your Windsor Heights Vacation

With all your travel plans organized before you go, our Windsor Heights vacation packages let you simply focus on having fun! One neighborhood to consider staying in this captivating city is Elm Grove, which is good for walking and history. If seeing the sights is a must during your trip to Windsor Heights, be sure to find your way to famous attractions like Oglebay Park and Oglebay Institute Glass Museum. A couple of clicks is all it takes to put together your ideal Windsor Heights vacation on Expedia.

Top Windsor Heights 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 $1,275, price is now CA $1,095 per person
CA $1,095
per person
Sep 11 - Sep 15
found 19 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
We enjoyed our two-night stay. The room was spacious and clean and comfy. The staff was very friendly and helpful. Breakfast was great.

Reviewed on Jul 11, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was CA $1,903, price is now CA $1,424 per person
CA $1,424
per person
Sep 11 - Sep 15
found 19 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
8/10 Very good! (302 reviews)
Affordable

Reviewed on Jul 4, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $1,779, price is now CA $1,476 per person
CA $1,476
per person
Sep 11 - Sep 15
found 19 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
8.6/10 Excellent! (146 reviews)
Property is a beautiful, historic building in a convenient location off the freeway. Our rooms were spacious, clean, and comfortable with the exception of no central air. A loud, mobile air unit was in two of the rooms. The blinds in one room could not close because of a missing wand. Also the roku was not working. Keep in mind hotel room is near train tracks. Staff was kind enough to meet us at the parking area door to let us into the building so that we could conveniently check in (some parking is near an amtrak station).

Reviewed on Jul 10, 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
Price was CA $1,858, price is now CA $1,549 per person
CA $1,549
per person
Sep 11 - Sep 15
found 19 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
8.4/10 Very good! (1,078 reviews)
Unclean toilet bowl, showel gel not refilled, no slippers, washroom smaller than a printing room in office space, just not comfortable for the price we paid. And in the parking they said there's only valet parking but didnt mention the price of $45. Just a scam and cheap mentality from such a huge institution.

Reviewed on Jul 12, 2026

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Price was CA $1,717, price is now CA $1,479 per person
CA $1,479
per person
Sep 11 - Sep 15
found 19 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
8.2/10 Very good! (1,283 reviews)
The property was clean and the staff was friendly... the bed was very comfortable... the ice machine always worked

Reviewed on Jul 10, 2026

Ready to book your vacation to Windsor Heights?

 

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Windsor Heights Hotel Deals

Wingate by Wyndham St. Clairsville/Wheeling

Wingate by Wyndham St. Clairsville/Wheeling

3 out of 5
51130 National Road E St. Clairsville OH
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Jul 19 to Jul 20
CA $112
CA $127 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Had everything we needed for our stay. Clean room and bed, decent breakfast. The staff was professional and courteous. We would stay there again"

Reviewed on Jul 7, 2026

Wingate by Wyndham St. Clairsville/Wheeling
Microtel Inn & Suites by Wyndham Wheeling at Highlands

Microtel Inn & Suites by Wyndham Wheeling at Highlands

2 out of 5
85 Fort Henry Rd Triadelphia WV
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Jul 20 to Jul 21
CA $106
CA $119 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (1,108 reviews)
"Everything was great as always"

Reviewed on Jul 8, 2026

Microtel Inn & Suites by Wyndham Wheeling at Highlands
Comfort Inn & Suites Triadelphia - Wheeling

Comfort Inn & Suites Triadelphia - Wheeling

2.5 out of 5
675 Fort Henry Rd Triadelphia WV
Fully refundable
The price is CA $99 per night from Aug 6 to Aug 7
CA $99
CA $111 total
Aug 6 - Aug 7
includes taxes & fees
8.4/10 Very good! (1,010 reviews)
"."

Reviewed on Jul 11, 2026

Comfort Inn & Suites Triadelphia - Wheeling
See all 139 properties in Windsor Heights
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

Frequently asked questions

How much does a Windsor Heights vacation package cost?
You can snap up a vacation package to this destination from CA $1,095 on Expedia. But how much your vacation to Windsor Heights costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Windsor Heights?
January, February and November are great times to search for cheap Windsor Heights vacation packages. Opting to travel in quieter periods means you can usually find better prices on flights and accommodations.
How many days is enough for Windsor Heights?
The ideal length for your Windsor Heights vacation depends on what you'd like to see. Generally, a few days to a week will give you time to go to all the top sights and explore some hidden gems along the way.
How to find the best Windsor Heights package deals?
Use Expedia's filters to help you find some unbeatable Windsor Heights package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Windsor Heights package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Windsor Heights vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and stays individually. Better still, you can personalize your Windsor Heights getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Windsor Heights?
If you're planning an impromptu Windsor Heights getaway, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Windsor Heights?

  1. Pick your dates: The things you want to do in Windsor Heights and your preferred season can help you decide when to get away.
  2. Set your budget: Factor in expenses such as flights, transportation and food when calculating how much to save for your trip to Windsor Heights. Then, select a property that matches your budget, whether that's an economical stay or a high-end retreat.
  3. Decide how long to go for: Now that you know more about Windsor Heights, you can figure out the perfect length of your vacation. Put together a draft itinerary and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Windsor Heights 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.