Windsor Heights Vacations from $241

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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.

The Latest Windsor Heights vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was $323, price is now $241 per person
$241
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
Very friendly staff. Extremely clean and large room.

Reviewed on Dec 13, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was $357, price is now $247 per person
$247
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.4/10 Very Good! (1,385 reviews)
clean and comfortable!

Reviewed on Dec 8, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Save 100% on your flight
Price was $576, price is now $404 per person
$404
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Nice hotel in downtown Pittsburgh. Room and common area were clean and well maintained.

Reviewed on Dec 8, 2025

Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Price was $466, price is now $348 per person
$348
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,253 reviews)
Room was immaculately cleaned. Staff was friendly and helpful.

Reviewed on Dec 9, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was $423, price is now $318 per person
$318
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Everyone I encountered was amazing through our experience related to our stay. There was an event occurring in the main entry way during our stay and the valet assisted us in locating parking, called the front desk and checked in from the door, they were very informative and helpful, even the building staff were very friendly and helpful helped us with the door on arrival. It would be nice to be able to use valet service, especially since it is paid parking anyways, and also enter through the nicer main lobby rather than a service entrance and padded frieght elevator... I did chose the Penn because of its prestige, location, amenities, and to view/enjoy craftsmanship of the architecture and chandilers specifically (as a former apprentice of the artist). Overall great stay.

Reviewed on Dec 9, 2025

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Windsor Heights Hotel Deals

Hampton Inn Wheeling

Hampton Inn Wheeling

3 out of 5
795 National Rd Wheeling WV
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $117 total per night from Dec 23 to Dec 24
$117 total
Dec 23 - Dec 24
Total with taxes and fees
9.4/10 Exceptional! (1,006 reviews)
Everything was extremely great

Reviewed on Dec 7, 2025

Hampton Inn Wheeling
Oglebay Resort

Oglebay Resort

3 out of 5
465 Lodge Dr. Wheeling WV
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $160 total per night from Dec 15 to Dec 16
$160 total
Dec 15 - Dec 16
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Clean room, friendly staff

Reviewed on Dec 13, 2025

Oglebay Resort
Wingate by Wyndham St. Clairsville/Wheeling

Wingate by Wyndham St. Clairsville/Wheeling

2.5 out of 5
51130 National Road E St. Clairsville OH
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $77 total per night from Dec 21 to Dec 22
$77 total
Dec 21 - Dec 22
Total with taxes and fees
9/10 Wonderful! (920 reviews)
Room wqs clean, brekafast was good, parking lot was plowed. Best hotel weve ever stayed in.

Reviewed on Dec 11, 2025

Wingate by Wyndham St. Clairsville/Wheeling
See all 110 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.

Find the Best Windsor Heights Vacation Packages

Windsor Heights Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Pittsburgh Intl. Airport (PIT)
Top Sights
Capitol Theater, Heritage Port Amphitheater and Scottish Rite Cathedral

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Frequently asked questions

How much does a Windsor Heights vacation package cost?
You'll find cheap prices from $241 on Expedia for your Windsor Heights getaway. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Windsor Heights costs.
What are the cheapest months to go to Windsor Heights?
If you'd like to book a cheap Windsor Heights vacation package, consider traveling in December, January and February. You'll usually find lower prices on hotels and airfares during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Windsor Heights?
The ideal length of your Windsor Heights vacation depends on what you'd like to see and do. Generally, a few days to a week will give you enough time to tick off all the main sights and discover some hidden treasures along the way.
How to find the best Windsor Heights package deals?
Begin your search for a Windsor Heights package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," 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 ideal Windsor Heights package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor Heights adventure underway.
Is it cheaper to book a Windsor Heights vacation as a package?
You can enjoy significant savings on your next Windsor Heights getaway by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to browse some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Windsor Heights?
If you're planning a spontaneous Windsor Heights adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Windsor Heights vacation packages?
Your Windsor Heights trip is meant to be an escape from your busy life, not a source of money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.