Stephensport Vacations from $495

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The Latest Stephensport vacation packages

Price found within the past 48 hours. Click for updated prices.
Hancock House

Hancock House

3 out of 5
Downtown Louisville
Price was $650, price is now $495 per person
$495
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Louisville (SDF)
8.2/10 Very Good! (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

Holiday Inn Express Louisville Airport Expo Center by IHG

Holiday Inn Express Louisville Airport Expo Center by IHG

2.5 out of 5
Hayfield Dundee
Price was $844, price is now $632 per person
$632
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Louisville (SDF)
8.6/10 Excellent! (1,001 reviews)
Very nice would stay here again

Reviewed on Nov 30, 2025

Hilton Garden Inn Louisville Downtown

Hilton Garden Inn Louisville Downtown

3.5 out of 5
Downtown Louisville
Price was $738, price is now $565 per person
$565
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Louisville (SDF)
8.4/10 Very Good! (1,000 reviews)
Staff was courteous. Great location. Will stay here again.

Reviewed on Dec 2, 2025

Hilton Garden Inn Louisville Mall of St. Matthews

Hilton Garden Inn Louisville Mall of St. Matthews

3 out of 5
St. Matthews
Price was $664, price is now $512 per person
$512
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Louisville (SDF)
9.4/10 Exceptional! (835 reviews)
Clean and comfortable room, staff was very courteous.

Reviewed on Dec 1, 2025

Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
Downtown Louisville
Price was $754, price is now $590 per person
$590
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Louisville (SDF)
9.2/10 Wonderful! (1,672 reviews)
Beautiful facilities, great staff, lots of spaces to explore, excellent food and beverage options. Very excited to return to this property!

Reviewed on Dec 7, 2025

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Stephensport Hotel Deals

Ramada by Wyndham Tell City

Ramada by Wyndham Tell City

2.5 out of 5
235 Orchard Hill Dr Tell City IN
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $95 total per night from Dec 28 to Dec 29
$95 total
Dec 28 - Dec 29
Total with taxes and fees
7.4/10 Good! (550 reviews)
Everything was great!! Staff was very helpful

Reviewed on Nov 30, 2025

Ramada by Wyndham Tell City
Holiday Inn Express Hotel & Suites Tell City by IHG

Holiday Inn Express Hotel & Suites Tell City by IHG

2.5 out of 5
310 Orchard Hill Dr Tell City IN
Fully refundable
$130 nightly
The price is $146 total per night from Jan 4 to Jan 5
$146 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8/10 Very Good! (510 reviews)
Came into town for my 45 class reunion! Clean, friendly, comfortable! No problem Will stay again when in town!!

Reviewed on Sep 8, 2025

Holiday Inn Express Hotel & Suites Tell City by IHG
Derby Time Riverside Cabin

Derby Time Riverside Cabin

Derby IN
10/10 Exceptional! (134 reviews)
We were looking to have a quiet, restful Thanksgiving, and this property was perfect for that. The view is beautiful, and the cabin is cozy and had everything we needed to settle in. We had a lovely time.

Reviewed on Nov 30, 2025

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Derby Time Riverside Cabin
See all 50 properties in Stephensport
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 Stephensport Vacation Packages

Stephensport Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Stephensport vacation package cost?
Offering excellent value package deals from $495 on Expedia, you'll be thrilled with how little a vacation to Stephensport costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Stephensport?
November, December and January are great times to look for cheap Stephensport vacation packages. Traveling in less busy periods means you can generally find reduced prices on flights and hotels.
How many days is enough for Stephensport?
Generally, a handful of days is enough to visit the top attractions during your Stephensport vacation. But if you want to have some time to kick back or take day trips, consider extending your trip.
How to find the best Stephensport package deals?
Finding a cheap Stephensport package deal is easy with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Stephensport package deals. Want a simple trick to score 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 a Stephensport vacation as a package?
You can enjoy significant savings on your Stephensport break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best hotel and flight 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 Stephensport?
If you have your Stephensport vacation dates finalized, book as soon as you can to score some unbeatable deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Stephensport vacation packages?
Your Stephensport break should be a relaxing escape from your daily routine, not a reason for money worries. So to give you more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.