Montgomery Vacations from $756
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The Latest Montgomery vacation packages
Price found within the past 48 hours. Click for updated prices.
New Harmony Inn Resort and Conference Center
$787
per person
Dec 28 - Jan 1
found 16 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Evansville (EVV)
9/10 Wonderful! (570 reviews)
Very Peaceful and well kept accommodations. Nearby work is a little noisy, but nice to see repairs happening. The large greenhouse pool looks very inviting and a run along the Wabash river along the trails had amazing views. So much to see & do here.
Reviewed on Oct 15, 2026
Hyatt Place Evansville
Downtown Evansville
$887
per person
Dec 24 - Dec 28
found 16 hours ago
Roundtrip non-stop flight included
San Francisco (SFO) to Evansville (EVV)
9.4/10 Exceptional! (1,004 reviews)
Great location, easy parking and the most friendly and helpful front lobby staff weve encountered in our travels. Room was comfortable and clean, breakfast had lots of healthy and tasty choices. Amazing fresh baked cookies! Two minor inconveniences, only one USB out-put for charging (charging block needed) and no microwave.
Reviewed on Oct 13, 2026
Montgomery Hotel Deals
Comfort Inn Jasper South
1970 Hospitality Drive Jasper IN
Fully refundable
$102 nightly
$114 total
Nov 5 - Nov 6
Total with taxes and fees
Baymont by Wyndham Washington
7 Cumberland Dr Washington IN
Fully refundableReserve now, pay when you stay
$107 nightly
$124 total
Nov 1 - Nov 2
Total with taxes and fees
Clarion Pointe Jasper
272 Brucke Strasse Jasper IN
Fully refundable
$93 nightly
$104 total
Nov 6 - Nov 7
Total with taxes and fees
9/10 Wonderful! (290 reviews)
"AC was very lackluster, room was very muggy even in october"
Reviewed on Oct 11, 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 $756 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.
