Montgomery Vacations from $643
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The Latest Montgomery vacation packages
Price found within the past 48 hours. Click for updated prices.
Howard Johnson by Wyndham Evansville East
$643
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Evansville (EVV)
8/10 Very Good! (1,002 reviews)
The rooms were dirty with stains on the chairs and bed. We had to switch to a different room then the pillows had hair on it. Not my hair. There was a crack in the bathtub. You only allowed two towels which are tiny and rough. Over half the outlets in the room didn’t work including the charging outlets to charge your phone. The rooms smelled. We tried three of them.
Reviewed on Aug 12, 2026
New Harmony Inn Resort and Conference Center
$794
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Evansville (EVV)
9/10 Wonderful! (549 reviews)
Very calm place. The town is a very quiet, peaceful place as well. If you are looking for a getaway where you just want to relax maybe take a bike ride or a nice walk. Do a little shopping in an adorable downtown. Enjoy a good meal this is the place for it.
Reviewed on Aug 9, 2026
Holiday Inn Express Princeton by IHG
$863
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Evansville (EVV)
8/10 Very Good! (362 reviews)
Probably the worst Holiday Inn Express … I checked into a room that hadn’t been cleaned and it was ex difficult understanding what the lady checking me in was saying. The pool was nice though.
Reviewed on Aug 9, 2026
Montgomery Hotel Deals
Jasper Inn
951 Wernsing Road Jasper IN
Fully refundableReserve now, pay when you stay
$85 nightly
$95 total
Sep 11 - Sep 12
Total with taxes and fees
8/10 Very Good! (808 reviews)
"We booked a king room. When we arrived, we were told there was a problem with the toilet in the room we booked so they would be putting us in a double queen room because we booked it through a 3rd party and the cost for the double queen was the same. I offered to pay the difference and she was unable ..."
Reviewed on Aug 12, 2026
Comfort Inn Jasper South
1970 Hospitality Drive Jasper IN
Fully refundable
$99 nightly
$111 total
Sep 11 - Sep 12
Total with taxes and fees
9.2/10 Wonderful! (617 reviews)
"Had a great stay. The room was clean. Breakfast had a lot of choices. The room was very quiet. Great place to stay after a day at Holiday World."
Reviewed on Aug 13, 2026
Fairfield Inn & Suites Jasper
333 River Centre Landing Jasper IN
Fully refundableReserve now, pay when you stay
$125 nightly
$140 total
Sep 11 - Sep 12
Total with taxes and fees
9.2/10 Wonderful! (437 reviews)
"Great location."
Reviewed on Aug 13, 2026
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 Montgomery Vacation Packages
Montgomery Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 340 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
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Frequently asked questions
How much does a Montgomery vacation package cost?
Offering excellent value package deals from $643 on Expedia, you'll be pleasantly surprised at how much a vacation to Montgomery costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Montgomery?
November, December and January are the best times to look for cheap Montgomery vacation packages. Traveling in quieter periods means you can usually find better prices on accommodations and flights.
How many days is enough for Montgomery?
With a well-organized itinerary, you can easily tick off the most popular Montgomery attractions in a few days. But if you'd like to discover hidden spots or take day trips, consider booking your Montgomery vacation for longer.
How to find the best Montgomery package deals?
Use Expedia's filters to help you find some great Montgomery package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Montgomery package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Montgomery 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 Montgomery escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Montgomery?
If you have your Montgomery vacation dates locked in, book as early as you can to grab some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
Does Expedia offer Book Now, Pay Later Montgomery vacation packages?
If you're like us, you love discovering new places but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Montgomery trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
