Montgomery Vacations from $540

Book a Hotel + Flight or Car together to unlock savings

The Latest Montgomery vacation packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Grayville
Residence Inn by Marriott Evansville East
Envi Boutique Hotel Henderson-Evansville South
New Harmony Inn Resort and Conference Center
Howard Johnson by Wyndham Evansville East
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Montgomery Hotel Deals

Comfort Inn

Comfort Inn

2.5 out of 5
1970 Hospitality Drive, Jasper, IN
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $100 total per night from Nov 24 to Nov 25
$100 total
Nov 24 - Nov 25
Total with taxes and fees
9/10 Wonderful! (524 reviews)
Room was clean as well as the property. Plenty of parking.

Reviewed on Oct 9, 2025

Comfort Inn
Clarion Pointe

Clarion Pointe

2.5 out of 5
272 Brucke Strasse, Jasper, IN
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $85 total per night from Nov 10 to Nov 11
$85 total
Nov 10 - Nov 11
Total with taxes and fees
8.8/10 Excellent! (174 reviews)
Friendly staff

Reviewed on Oct 19, 2025

Clarion Pointe
Holiday Inn Express Hotel & Suites Jasper by IHG

Holiday Inn Express Hotel & Suites Jasper by IHG

2.5 out of 5
2000 Hospitality Dr, Jasper, IN
Fully refundable
$78 nightly
The price is $87 total per night from Nov 23 to Nov 24
$87 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (493 reviews)
Pool was nice whole place was nice

Reviewed on Oct 10, 2025

Holiday Inn Express Hotel & Suites Jasper by IHG
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 $540 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.