Upland Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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

  • Rest easy

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

Find the Best Upland Vacation Packages

Upland Hotel Deals

Trojan Hideaway on First Street

Trojan Hideaway on First Street

Upland IN
The price is SARĀ 332 per night from Jul 20 to Jul 21
SARĀ 332
SARĀ 849 total
20 Jul - 21 Jul
includes taxes & fees
10/10 Exceptional! (11 reviews)
"Perfect for my mother in law and her sister!"

Reviewed on 30 July 2025

Trojan Hideaway on First Street
mi casa es TU casa (WEST)

mi casa es TU casa (WEST)

Upland IN
The price is SARĀ 324 per night from Aug 2 to Aug 3
SARĀ 324
SARĀ 560 total
2 Aug - 3 Aug
includes taxes & fees
10/10 Exceptional! (17 reviews)
"Clean and well furnished"

Reviewed on 30 June 2026

mi casa es TU casa (WEST)
mi casa es TU casa (Center)

mi casa es TU casa (Center)

Upland IN
The price is SARĀ 548 per night from Jul 19 to Jul 20
SARĀ 548
SARĀ 864 total
19 Jul - 20 Jul
includes taxes & fees
10/10 Exceptional! (11 reviews)
"Stocked with everything we needed, clean, comfortable, great neighborhood super close to campus, loved the yard!"

Reviewed on 11 June 2026

mi casa es TU casa (Center)
See all 136 properties in Upland
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.

Stay near popular Upland attractions

Taylor University

9.2/10 (37 reviews)
Founded in 1846, Taylor University blends rigorous academics with Christian faith in a close-knit community. Visitors can experience chapel services and explore the historic architecture amid green spaces.
See properties

Frequently asked questions

How much does an Upland vacation package cost?
You can snap up a vacation package to this top destination on Expedia. However, how much your vacation to Upland costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Upland?
If you're looking to snag a cheap Upland vacation package, consider visiting in January, February and March. You'll typically find better rates on hotels and airfares during these months ā€” perfect for budget-conscious travelers.
How to find the best Upland package deals?
Start your search for an Upland package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Upland package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Upland escape underway.
Is it cheaper to book an Upland vacation as a package?
You can enjoy significant savings on your Upland getaway by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Upland?
If you've got your Upland travel dates confirmed, book as soon as you can to bag some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Upland?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Upland.
  2. Budget wisely: Besides the cost of your stay, you should consider other expenses. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that could arise during your trip to Upland.
  3. Decide how long to go for: Now that you know more about Upland, you can work out the ideal length of your vacation. Put together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose an Upland vacation package that brings all your bookings together.