Underwood Vacations from $323

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The Latest Underwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Louisville Airport Expo Ctr by IHG

Crowne Plaza Louisville Airport Expo Ctr by IHG

3.5 out of 5
Fairgrounds
Price was $382, price is now $323 per person
$323
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
8.8/10 Excellent! (771 reviews)
The hotel was ok. Probably wouldn't stay here again though. We were suppose to have a shuttle service to pick up from the airport and shuttle service never came so we ended up paying for a Lyft. The hostess at the hotel told us the restaurant and bar were closed when we arrive at 10 pm, however we later found out the bar closed at midnight and the restaurant was in fact open until 11. We just wish the hotel communicated better. As far as booking with Expedia the rates that we reserved our room at or more expensive than the rates available on Expedia the night of check-in.

Reviewed on Aug 31, 2025

Derby City Gaming & Hotel - A Churchill Downs Property

Derby City Gaming & Hotel - A Churchill Downs Property

4 out of 5
Price was $436, price is now $360 per person
$360
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
9.4/10 Exceptional! (1,388 reviews)
The best hotel, casino, and restaurant options around. Everything and everyone was Amazing!!! Highly recommend!!!

Reviewed on Aug 30, 2025

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $436, price is now $362 per person
$362
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Louisville (SDF)
9/10 Wonderful! (1,001 reviews)
Clean and comfortable

Reviewed on Aug 27, 2025

Regina's Country Livin'

Regina's Country Livin'

3 out of 5
Price was $568, price is now $473 per person
$473
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Louisville (SDF)
10/10 Exceptional! (6 reviews)
Driving up to the property was grand. Inside of the house is breathtaking. It was peaceful and comfortable. Our hostess was very welcoming and an absolute fabulous cook. I will revisit again and again, as it felt like going home to family.

Reviewed on Apr 29, 2025

Hawthorn Suites by Wyndham Louisville East

Hawthorn Suites by Wyndham Louisville East

3 out of 5
St. Matthews
Price was $661, price is now $558 per person
$558
per person
Oct 22 - Oct 27
found 2 days ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Louisville (SDF)
8.8/10 Excellent! (1,006 reviews)
I’ve used this hotel for about a year now when visiting loved ones in Louisville. Very friendly and accommodating.

Reviewed on Aug 26, 2025

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Underwood Hotel Deals

Hilton Garden Inn Jeffersonville Louisville North

Hilton Garden Inn Jeffersonville Louisville North

3 out of 5
4900 Water Tower Road, Jeffersonville, IN
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $109 total per night from Sep 5 to Sep 6
$109 total
Sep 5 - Sep 6
Total with taxes and fees
Hilton Garden Inn Jeffersonville Louisville North
Holiday Inn Express & Suites Scottsburg by IHG

Holiday Inn Express & Suites Scottsburg by IHG

2.5 out of 5
200 S Beechwood Ave, Scottsburg, IN
Fully refundable
$114 nightly
The price is $128 total per night from Sep 7 to Sep 8
$128 total
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Express & Suites Scottsburg by IHG
Ramada by Wyndham Sellersburg/Louisville North

Ramada by Wyndham Sellersburg/Louisville North

2.5 out of 5
360 Triangle Dr, I-65 Exit 9, Sellersburg, IN
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $90 total per night from Sep 7 to Sep 8
$90 total
Sep 7 - Sep 8
Total with taxes and fees
Ramada by Wyndham Sellersburg/Louisville North
See all 133 properties in Underwood
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.

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Frequently asked questions

How much does an Underwood vacation package cost?
You can grab a vacation package to this destination from $323 on Expedia. However, how much your vacation to Underwood costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Underwood?
If you're looking to score a cheap Underwood vacation package, consider traveling in February, October and December. You'll generally find lower prices on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Underwood?
The ideal length of your Underwood vacation depends on what you'd like to see. Generally, a handful of days to a week will give you time to check out all the major sights and discover some hidden spots along the way.
How to find the best Underwood package deals?
Finding a cheap Underwood package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most economical Underwood 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 often lower.
Is it cheaper to book an Underwood vacation as a package?
You can enjoy significant savings on your Underwood retreat by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Underwood?
If you've got your Underwood travel dates locked in, book early to bag some outstanding deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Underwood?

  1. Choose when to travel: Check your calendar and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to vacation in Underwood.
  2. Plan your budget wisely: As well as the cost of your accommodations, you'll need to consider other expenses too. These include food, transportation and flights. Also, put aside some extra funds for unexpected costs that may come up during your trip to Underwood.
  3. Use Expedia's trip planning tool to explore Underwood: Research every aspect of your trip to Underwood with this handy planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide your trip length: Consider how long you'd like to spend discovering Underwood. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a tailored Underwood vacation package.
  6. Book any activities or excursions: Now to the fun part — locking in everything you want to do and see. Explore some of the top things to do in Underwood and book your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Underwood vacation packages?
Jet off on your perfect escape to Underwood with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or wait for your next paycheck — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stay on budget and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.