Montgomery Vacations from $346
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The Latest Montgomery vacation packages
Price found within the past 48 hours. Click for updated prices.
Quality Inn & Suites Rockport - Owensboro North (GOLD AWARD WINNER)
$442
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Evansville (EVV)
8.2/10 Very Good! (421 reviews)
My entire three-day experience was very pleasant. Hotel staff were friendly and helpful. My room was very comfortable. I appreciated the soaps, hair products and other health and beauty aids. The breakfast was very convenient. I was intrigued by the privacy shade on the window, where I could see out but which provided total privacy. My only problem during my stay, which was in no way connected with the hotel, was that coming back from Owensboro to the south, the highway exit leading to the hotel was blocked due to road construction. However, there was a turnaround a mile or so up the road. I will definitely plan to make reservations at this hotel during my future trips to the Owensboro area.
Reviewed on Aug 28, 2026
Montgomery Hotel Deals
Jasper Inn
951 Wernsing Road Jasper IN
Fully refundableReserve now, pay when you stay
$82 nightly
$92 total
Sep 11 - Sep 12
Total with taxes and fees
8/10 Very Good! (833 reviews)
"Quiet and clean"
Reviewed on Sep 3, 2026
Comfort Inn Jasper South
1970 Hospitality Drive Jasper IN
Fully refundable
$98 nightly
$110 total
Sep 10 - Sep 11
Total with taxes and fees
9.2/10 Wonderful! (632 reviews)
"Very comfortable room and excellent breakfast!"
Reviewed on Aug 29, 2026
Baymont by Wyndham Washington
7 Cumberland Dr Washington IN
Fully refundableReserve now, pay when you stay
$111 nightly
$129 total
Oct 4 - Oct 5
Total with taxes and fees
8/10 Very Good! (728 reviews)
"Staff always very pleasant and friendly."
Reviewed on Aug 31, 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 $346 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.
