Montgomery Vacations from $587

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.
Baymont by Wyndham Evansville North/Haubstadt

Baymont by Wyndham Evansville North/Haubstadt

2.5 out of 5
Price was $640, price is now $587 per person
$587
per person
Jul 28 - Aug 1
found 3 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Evansville (EVV)
7.6/10 Good! (1,001 reviews)
Rooms were clean but very outdated. Comforter on bed had a stain and there was barely anything for breakfast. Quick night ok to get back on road but that's it.

Reviewed on May 15, 2026

Hilltop Country Home with Hot Tub 2049

Hilltop Country Home with Hot Tub 2049

2 out of 5
Price was $1,379, price is now $1,256 per person
$1,256
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Greensboro (GSO) to Evansville (EVV)
2/10 (1 review)
Holiday Inn Owensboro Riverfront by IHG

Holiday Inn Owensboro Riverfront by IHG

3 out of 5
Price was $1,364, price is now $1,271 per person
$1,271
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Greensboro (GSO) to Evansville (EVV)
9.4/10 Exceptional! (788 reviews)
Mike who i assume is the property manager was absolutely amazing, and the housekeeper Stephanie was very professional and respectful.

Reviewed on Apr 15, 2026

Best Budget Inn

Best Budget Inn

2.5 out of 5
Price was $857, price is now $800 per person
$800
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Greensboro (GSO) to Evansville (EVV)
5.2/10 (247 reviews)
The room was okay in and of itself. People that run it were very nice. Three major problems. First the main heating unit didn't work They had a very small heater that sucked. I had to go out and buy one. Secondly, the power kept going out. I couldn't use two heaters and watch TV at the same time. Power went out five times. I had to settle for not being able to watch TV or freeze my butt off. Third problem was that the toilet became stopped up and I couldn't get it unclogged with the plunger that was in the room. Bottom line is that they should have offered me another room. There were more empty rooms available but they didn't mention moving me to one that at least had heat. Before I would stay there again I would make sure that the room was properly heated and that I could watch TV and not have to worry about the power going out

Reviewed on Jan 9, 2026

Holiday Inn Express Evansville West by IHG

Holiday Inn Express Evansville West by IHG

2.5 out of 5
Price was $654, price is now $610 per person
$610
per person
Jul 7 - Jul 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Evansville (EVV)
8.6/10 Excellent! (573 reviews)
The location was great. Well lit parking lot. Loved the room darkening shade. Comfy beds and fluffy pillows. Enjoyed a warm breakfast. Definitely would recommend.

Reviewed on Jun 1, 2026

Don't see what you're looking for?
See all available trips from Columbus to Montgomery
View all trips

Montgomery Hotel Deals

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
$118 nightly
The price is $137 total per night from Jun 14 to Jun 15
$137 total
Jun 14 - Jun 15
Total with taxes and fees
8.2/10 Very Good! (703 reviews)
"Everything was great!"

Reviewed on May 31, 2026

Baymont by Wyndham Washington
Jasper Inn

Jasper Inn

2.5 out of 5
951 Wernsing Road Jasper IN
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $95 total per night from Jun 7 to Jun 8
$95 total
Jun 7 - Jun 8
Total with taxes and fees
8/10 Very Good! (726 reviews)
"The staff was so helpful and nice. Our room was clean and the bed comfortable. We appreciate the variety in the breakfast."

Reviewed on Jun 2, 2026

Jasper Inn
Comfort Inn Jasper South

Comfort Inn Jasper South

2.5 out of 5
1970 Hospitality Drive Jasper IN
Fully refundable
$112 nightly
The price is $125 total per night from Jun 10 to Jun 11
$125 total
Jun 10 - Jun 11
Total with taxes and fees
9.2/10 Wonderful! (570 reviews)
"Great staff. Very good continental breakfast."

Reviewed on May 24, 2026

Comfort Inn Jasper South
See all 47 properties in Montgomery
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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Montgomery vacation package cost?
Offering excellent value package deals from $587 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.