Montgomery Vacations from $804

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The Latest Montgomery vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Evansville North by IHG
Residence Inn by Marriott Evansville East
New Harmony Inn Resort and Conference Center
Envi Boutique Hotel Henderson-Evansville South
FairBridge Inn Express Mount Vernon
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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
$97 nightly
The price is $108 total per night from Nov 3 to Nov 4
$108 total
Nov 3 - Nov 4
Total with taxes and fees
9.2/10 Wonderful! (518 reviews)
"Parking safe and roomy! Staff was excellent! Room was very clean! AC was on point! Exhaust fan in the bathroom didn't come on in 302...other than that we will be back! Thank you!!!"

Reviewed on Oct 6, 2025

Comfort Inn
Fairfield Inn & Suites Jasper

Fairfield Inn & Suites Jasper

2.5 out of 5
333 River Centre Landing, Jasper, IN
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $137 total per night from Oct 17 to Oct 18
$137 total
Oct 17 - Oct 18
Total with taxes and fees
9.2/10 Wonderful! (376 reviews)
"Excellent work from mgt change for extra day and bonvoy points given"

Reviewed on Sep 27, 2025

Fairfield Inn & Suites Jasper
Baymont by Wyndham Washington

Baymont by Wyndham Washington

2.5 out of 5
7 Cumberland Dr, Washington, IN
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $110 total per night from Nov 1 to Nov 2
$110 total
Nov 1 - Nov 2
Total with taxes and fees
8/10 Very Good! (638 reviews)
"Room was dirty and bathtub did not drain"

Reviewed on Oct 4, 2025

Baymont by Wyndham Washington
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.

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 $804 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.