Upland Vacations from $574

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    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

Your Upland Vacation

With a vacation package to Upland, say goodbye to endless planning and hello to hassle-free adventure. Every detail of your journey has been taken care of before you depart, so you can get on with discovering this fantastic city. Every good trip to Upland just has to include some sightseeing. Where to first? Taylor University and Walnut Creek Golf Courses are leading attractions. Don't put off exploring this city any longer. Your perfect Upland vacation is just a few clicks away with Expedia.

The Latest Upland vacation packages

Price found within the past 48 hours. Click for updated prices.
The village

The village

4 out of 5
Near Westside
Price was $738, price is now $574 per person
$574
per person
May 15 - May 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Indianapolis (IND)
8/10 Very Good! (46 reviews)
Would definitely stay again!

Reviewed on Mar 6, 2026

Ironworks Hotel Indy

Ironworks Hotel Indy

4 out of 5
Price was $1,033, price is now $789 per person
$789
per person
Jun 23 - Jun 26
found 5 hours ago
Roundtrip flight included
Austin (AUS) to Indianapolis (IND)
9.8/10 Exceptional! (1,855 reviews)
Beautiful place, staff great, Provisions Bar was very accommodating and great! This is a great place to stay!

Reviewed on Apr 12, 2026

Windsor Park Pad apt 2 min to Mass Ave With AC

Windsor Park Pad apt 2 min to Mass Ave With AC

2 out of 5
Near Eastside
Save 100% on your flight
Price was $3,356, price is now $2,607 per person
$2,607
per person
May 21 - May 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Indianapolis (IND)
No reviews
The Bradley Hotel

The Bradley Hotel

4 out of 5
Downtown
Price was $953, price is now $749 per person
$749
per person
May 21 - May 25
found 24 hours ago
Roundtrip flight included
Minneapolis (MSP) to Fort Wayne (FWA)
9.4/10 Exceptional! (1,007 reviews)
Clean comfortable rooms with nice decor.

Reviewed on Apr 9, 2026

Executive Inn

Executive Inn

2 out of 5
Price was $847, price is now $667 per person
$667
per person
May 21 - May 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Indianapolis (IND)
6.6/10 (92 reviews)
They were ok. Smelled like xurry the hole time.

Reviewed on Apr 1, 2026

Don't see what you're looking for?
See all available trips from Columbus to Upland
View all trips

Discover the most popular places to visit in Upland

Taylor University

Enjoy the collegiate vibe at Taylor University during your visit to Upland.

Taylor University

Upland Hotel Deals

mi casa es TU casa (WEST)

mi casa es TU casa (WEST)

Upland IN
$136 nightly
The price is $149 total per night from Apr 15 to Apr 16
$149 total
Apr 15 - Apr 16
Total with taxes and fees
10/10 Exceptional! (15 reviews)
Super convenient location. Clean, comfortable and easy check in process. Nicely appointed. Will definitely stay here again!

Reviewed on Mar 19, 2026

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

mi casa es TU casa (Center)

Upland IN
$206 nightly
The price is $226 total per night from Apr 26 to Apr 27
$226 total
Apr 26 - Apr 27
Total with taxes and fees
9.8/10 Exceptional! (9 reviews)
We walked in the door, and what a relief after a long drive! The apartment is beautifully done and super clean. Comfortable seating, great beds and bedding, towels, and kitchen equipment (some of the best knives and pots and pans we've ever had). The one challenge was the bathroom lighting. Difficult ...

Reviewed on Mar 24, 2026

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

Trojan Hideaway on First Street

Upland IN
$201 nightly
The price is $213 total per night from Apr 14 to Apr 15
$213 total
Apr 14 - Apr 15
Total with taxes and fees
10/10 Exceptional! (11 reviews)
Perfect for my mother in law and her sister!

Reviewed on Jul 30, 2025

Trojan Hideaway on First Street
See all 131 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.

Find the Best Upland Vacation Packages

Upland Essential Information

Language
English
Currency
U.S dollars
Population
3,800
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
The Quilters Hall of Fame, Indiana Wesleyan University and Taylor University

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Upland vacation package cost?
Offering excellent value package deals from $574 on Expedia, you'll be surprised at how little a vacation to Upland costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Upland?
January, March and December are great times to look for cheap Upland vacation packages. Opting to travel in quieter months means you can generally find lower prices on accommodations and flights.
How many days is enough for Upland?
With a well-organized travel plan, you can easily tick off the main Upland sights in a handful of days. But if you want to discover hidden spots or go on day tours, think about booking your Upland vacation for longer.
How to find the best Upland package deals?
Landing a cheap Upland package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and browse what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Upland package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book an Upland vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component individually. And you'll still have the freedom to create a tailored Upland vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Upland?
If you have your Upland vacation dates locked in, book early to grab some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for traveling on a whim.
Does Expedia offer Book Now, Pay Later Upland vacation packages?
Your Upland getaway should be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you that extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

Explore a world of travel with Expedia

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