Montgomery Vacations from $566
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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
$566
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Oklahoma City (OKC) to Evansville (EVV)
8/10 Very Good! (1,005 reviews)
For the price, this stay was exactly what we needed. Just a quick overnight. Staff was kind. We checked in quickly. Place is old, but clean. And for the price it was great.
Reviewed on Oct 21, 2026
New Harmony Inn Resort and Conference Center
$638
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Oklahoma City (OKC) to Evansville (EVV)
9/10 Wonderful! (570 reviews)
The hotel and rooms smelled amazing, everything in the hotel was locally-made (except perhaps the shampoo) including the furniture, the venue is extremely convenient at a block or so from the main downtown area, and right next door to a fabulous restaurant that serves breakfast, lunch, and dinner. The bed was a little creaky, but the mattress, sheets, and pillows were comfortable and the lavender sachet provided in the room made everything smell relaxing and wonderful. I do not know if the hotel is pet-friendly, and I think that they do not have a breakfast, but I am fortunate that that didn’t matter to me this visit. I am already looking forward to booking again in the future.
Reviewed on Oct 19, 2026
Montgomery Hotel Deals
Comfort Inn Jasper South
1970 Hospitality Drive Jasper IN
Fully refundable
$102 nightly
$114 total
Nov 12 - Nov 13
Total with taxes and fees
9.2/10 Wonderful! (659 reviews)
"The property pictures were deceiving. The pool (one is the main reasons for booking this property) was the size of a postage stamp. The staff were friendly and helpful but our room was extremely noisy. There was so much noise coming through the walls/ceiling from other guests during all three nights ..."
Reviewed on Oct 19, 2026
Baymont by Wyndham Washington
7 Cumberland Dr Washington IN
Fully refundableReserve now, pay when you stay
$105 nightly
$121 total
Nov 1 - Nov 2
Total with taxes and fees
Clarion Pointe Jasper
272 Brucke Strasse Jasper IN
Fully refundable
$79 nightly
$89 total
Nov 19 - Nov 20
Total with taxes and fees
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 $566 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.