Upton Vacations from $421

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The Latest Upton vacation packages

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Hancock House

Hancock House

3 out of 5
Downtown Louisville
Price was $527, price is now $421 per person
$421
per person
Jan 16 - Jan 19
found 12 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Louisville (SDF)
16.4/10 Exceptional! (245 reviews)
The apartment was so elegant with an antique vibe. It had high ceilings and lots of tall windows with drapes and blackout blinds. Modern stainless steel kitchen appliances. I really liked that it had an icemaker and lamps in every room. Besides the stairs you couldn’t hear the neighbors.The host made things even more convenient by providing late or early check in, late check out or the option to add an extra night right from the confirmation email of your booking. If you like wholesome comfort and simple amenities you would love this charming apartment stay.

Reviewed on Oct 31, 2025

Caesars Southern Indiana - A Caesars Rewards Destination

Caesars Southern Indiana - A Caesars Rewards Destination

3.5 out of 5
Price was $622, price is now $482 per person
$482
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Louisville (SDF)
16.4/10 Exceptional! (1,002 reviews)
Check in was easy. Room was clean. Check out was easy.

Reviewed on Nov 21, 2025

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was $880, price is now $694 per person
$694
per person
Dec 24 - Dec 28
found 1 hour ago
Roundtrip flight included
Denver (DEN) to Louisville (SDF)
17.6/10 Exceptional! (1,005 reviews)
Staff very friendly and room was clean. You had to swipe your key for the floor you were going to

Reviewed on Nov 17, 2025

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was $1,001, price is now $813 per person
$813
per person
Dec 24 - Dec 28
found 1 hour ago
Roundtrip flight included
Denver (DEN) to Louisville (SDF)
19.2/10 Exceptional! (422 reviews)
Beautiful hotel! And the southern hospitality was the best!! Plus the Repeal steakhouse was top notch - excellent!

Reviewed on Nov 4, 2025

The Grady

The Grady

4 out of 5
Downtown Louisville
Price was $990, price is now $821 per person
$821
per person
Dec 24 - Dec 28
found 1 hour ago
Roundtrip flight included
Denver (DEN) to Louisville (SDF)
18.8/10 Exceptional! (1,001 reviews)
The room and hotel were excellent! I would not recommend The Swann restaurant however. Long wait and poor attitude of staff

Reviewed on Nov 21, 2025

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Find the Best Upton Vacation Packages

Upton Essential Information

Language
English
Currency
U.S dollars
Population
670

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Frequently asked questions

How much does an Upton vacation package cost?
You'll find cheap prices from $421 on Expedia for your Upton getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Upton costs.
What are the cheapest months to go to Upton?
November, December and January are the best times to search for cheap Upton vacation packages. Opting to travel in less busy periods means you'll typically find better prices on hotels and flights.
How many days is enough for Upton?
The ideal length for your Upton vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you time to tick off all the top sights and explore some hidden spots along the way.
How to find the best Upton package deals?
Finding a cheap Upton package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Upton package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Upton vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and stays individually. Better still, you can personalize your Upton trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Upton?
If you have your Upton vacation dates confirmed, book early to bag some outstanding deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Upton vacation packages?
Secure your dream getaway to Upton with our Book Now, Pay Later vacations. No need to save like crazy or wait until your next payday — we've partnered with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stay on budget and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.