Upland Vacations from ￥309,558

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The Latest Upland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Park Inn Motel

Park Inn Motel

2.5 out of 5
Price was ￥313,942, price is now ￥309,558 per person
￥309,558
per person
Dec 25 - Dec 29
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Indianapolis (IND)
7.2/10 Good! (30 reviews)
The property is starting to show its age. The property needs a fresh overhaul.

Reviewed on Oct 7, 2026

Pleasant Grove Farm LLC

Pleasant Grove Farm LLC

3 out of 5
Price was ￥328,920, price is now ￥327,420 per person
￥327,420
per person
Dec 25 - Dec 29
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Indianapolis (IND)
9.4/10 Exceptional! (105 reviews)
We love staying here. We travel to Indiana 1 to 2 times a year and always stay here. It is a really quiet place and always clean. The staff and owners are extremely nice and helpful. We highly recommend stay there. Checking in is always super easy and if you need anything, you can ask and they have always be extremely accommodating. Five stars for sure!!

Reviewed on Jul 2, 2026

Pleasant Grove Inn LLC

Pleasant Grove Inn LLC

3 out of 5
Price was ￥324,234, price is now ￥323,316 per person
￥323,316
per person
Dec 25 - Dec 29
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Indianapolis (IND)
10/10 Exceptional! (101 reviews)
The atmosphere is very quaint, property is off the beaten path and quiet! We love this place and have been here a few times! They also have very cool cottages you should check out as well!

Reviewed on Oct 26, 2026

Find the Best Upland Vacation Packages

Upland Hotel Deals

mi casa es TU casa (WEST)

mi casa es TU casa (WEST)

Upland IN
The price is ￥13,613 per night from Nov 2 to Nov 3
￥13,613
￥20,856 total
Nov 2 - Nov 3
includes taxes & fees
10/10 Exceptional! (19 reviews)
"Great location and just so cute. We stay here whenever we can."

Reviewed on Aug 31, 2026

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

mi casa es TU casa (Center)

Upland IN
The price is ￥22,972 per night from Nov 2 to Nov 3
￥22,972
￥33,267 total
Nov 2 - Nov 3
includes taxes & fees
10/10 Exceptional! (12 reviews)
"The house was clean. The pictures describe it perfectly. There are two bedrooms each with a king size bed. One bed was a little firmer. The other bed a little softer. Both were comfortable for the people who chose them. Plenty of towels and wash clothes in the bathroom. The water pressure was great ..."

Reviewed on Sep 6, 2026

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

Trojan Hideaway on First Street

Upland IN
The price is ￥13,936 per night from Nov 1 to Nov 2
￥13,936
￥34,011 total
Nov 1 - Nov 2
includes taxes & fees
10/10 Exceptional! (14 reviews)
STAY ON FIRST STREET 10/11 TO 10/14
"My kids and I had a very pleasant stay at the house. It worked out perfectly while we visited my daughter at Taylor. Very convenient for both my daughter and us. The bed in the master was VERY comfortable, I slept really well because of that. Thanks to Austin for accommodating my requests. We shall ..."

Reviewed on Oct 16, 2026

Trojan Hideaway on First Street
See all 144 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?
Offering excellent value package deals from ￥309,558 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, February and March are great times to search for cheap Upland vacation packages. Opting to travel in quieter months means you can usually find reduced prices on flights and hotels.
How many days is enough for Upland?
The ideal length for your Upland vacation depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to hit all the main attractions and explore some hidden treasures along the way.
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.
How to plan a trip to Upland?

  1. Choose when to travel: Check your calendar and get packing. Your preferred season and the activities available will also help you decide when to escape to Upland.
  2. Calculate your budget: Ensure you have enough money to pay for everything from meals and transportation to flights and experiences. Your accommodations will probably be the largest expense during your trip to Upland.
  3. Work out your trip length: Consider how long you'd like to spend discovering Upland. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, book the right Upland vacation package for you.

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