Upland Vacations from $219

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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.
Sonesta Essential Indianapolis Airport

Sonesta Essential Indianapolis Airport

3.5 out of 5
Price was $268, price is now $219 per person
$219
per person
Oct 2 - Oct 4
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
8.6/10 Excellent! (1,006 reviews)
Easy access. Clean. Staff friendly. Walking distance to eat. Felt safe during stay.

Reviewed on Jul 13, 2026

Cascades Inn

Cascades Inn

2 out of 5
Save 100% on your flight
Price was $1,324, price is now $1,028 per person
$1,028
per person
Sep 18 - Sep 20
found 11 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Indianapolis (IND)
8.6/10 Excellent! (1,003 reviews)
Great budget hotel. Property is aging, but being kept up - very eclectic! Staff is very kind. We've stayed many times with zero issues. Property is adjacent to a beautiful park, but requires being able to descend and climb a fairly big hill. The path is clean and groomed, but requires some degree of athleticism. Continental Breakfast is adequate and a great perk.

Reviewed on Jul 14, 2026

Hilton Garden Inn Bloomington

Hilton Garden Inn Bloomington

3 out of 5
Downtown Bloomington
Save 100% on your flight
Price was $2,969, price is now $2,337 per person
$2,337
per person
Sep 18 - Sep 20
found 11 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Indianapolis (IND)
8.6/10 Excellent! (1,002 reviews)
Good stay… clean hotel and nice staff

Reviewed on Jul 15, 2026

Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

Hotel Indy, Indianapolis, a Tribute Portfolio Hotel

4 out of 5
Downtown Indianapolis
Price was $412, price is now $328 per person
$328
per person
Oct 2 - Oct 4
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Indianapolis (IND)
9.2/10 Wonderful! (393 reviews)
Spacious room. Clean room, beds and bathroom. Comfortable bed. Valet was great. No microwave was a downer.

Reviewed on Jul 15, 2026

Royal Inn Rockville IN by Hotel O

Royal Inn Rockville IN by Hotel O

3 out of 5
Price was $717, price is now $584 per person
$584
per person
Aug 19 - Aug 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Indianapolis (IND)
7.2/10 Good! (344 reviews)
Quiet, pleasant easy check-in and out. Room was spacious. Low cost. Set back from the highway in nice rural setting

Reviewed on Jun 24, 2026

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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

Upland Hotel Deals

Trojan Hideaway on First Street

Trojan Hideaway on First Street

Upland IN
$212 nightly
The price is $226 total per night from Jul 19 to Jul 20
$226 total
Jul 19 - Jul 20
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
mi casa es TU casa (Center)

mi casa es TU casa (Center)

Upland IN
$210 nightly
The price is $230 total per night from Jul 19 to Jul 20
$230 total
Jul 19 - Jul 20
Total with taxes and fees
10/10 Exceptional! (11 reviews)
"Stocked with everything we needed, clean, comfortable, great neighborhood super close to campus, loved the yard!"

Reviewed on Jun 11, 2026

mi casa es TU casa (Center)
mi casa es TU casa (EAST)

mi casa es TU casa (EAST)

Upland IN
$153 nightly
The price is $169 total per night from Jul 19 to Jul 20
$169 total
Jul 19 - Jul 20
Total with taxes and fees
10/10 Exceptional! (5 reviews)
"We LOVED this property! It is extremely clean, well decorated, and stocked. The bed was especially comfortable, and both my daughter and I slept well. If you are visiting Taylor University it is close to campus. There are three units on the property, and the walls are not soundproof, but they have ..."

Reviewed on Jun 23, 2026

mi casa es TU casa (EAST)
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.

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

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Frequently asked questions

How much does an Upland vacation package cost?
Offering excellent value package deals from $219 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.

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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.