Montgomery Vacations from $665

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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 $714, price is now $665 per person
$665
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Evansville (EVV)
7.6/10 Good! (1,001 reviews)
Easy check in. Very clean facility and room. Would stay again. Won’t beat what is offered for the price. Only negative would be to add a few more breakfast items.

Reviewed on Jun 26, 2026

Holiday Inn Express Evansville West by IHG

Holiday Inn Express Evansville West by IHG

2.5 out of 5
Price was $809, price is now $715 per person
$715
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Evansville (EVV)
8.6/10 Excellent! (582 reviews)
The morning staff were very friendly and helpful. The lady at the desk helped me find an ice machine. A nice gentleman and I chatted about my love for the cinnamon rolls you can only find at their hotels. And the breakfast attendant kept everything clean, and even packed up an extra cinnamon roll for us to take along. We left there ready for a good day.

Reviewed on Jun 24, 2026

New Harmony Inn Resort and Conference Center

New Harmony Inn Resort and Conference Center

3 out of 5
Price was $843, price is now $770 per person
$770
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Evansville (EVV)
9/10 Wonderful! (534 reviews)
Restaurant on site- we did not visit but it looked nice!

Reviewed on Jun 28, 2026

Fairfield Inn By Marriott Evansville East

Fairfield Inn By Marriott Evansville East

3 out of 5
Price was $759, price is now $703 per person
$703
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Evansville (EVV)
8.6/10 Excellent! (508 reviews)
The interactions with staff were awful. They were rude and unhelpful. They made an already difficult situation even more stressful. The pool was closed the entire stay which was disappointing. Free breakfast wasn’t even worth eating.

Reviewed on Jun 21, 2026

Residence Inn by Marriott Evansville East

Residence Inn by Marriott Evansville East

3 out of 5
Price was $797, price is now $741 per person
$741
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Evansville (EVV)
8.6/10 Excellent! (544 reviews)
I liked the property very much, beautiful flowers/bushes onsite, a pond across the street, very safe neighborhood and the hot breakfast was perfect for me.

Reviewed on Jun 23, 2026

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Montgomery Hotel Deals

Jasper Inn

Jasper Inn

2.5 out of 5
951 Wernsing Road Jasper IN
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $100 total per night from Jul 9 to Jul 10
$100 total
Jul 9 - Jul 10
Total with taxes and fees
8/10 Very Good! (743 reviews)
"It was nice and clean and comfortable. Breakfast was good. It was quiet. Staff was friendly."

Reviewed on Jun 30, 2026

Jasper Inn
Comfort Inn Jasper South

Comfort Inn Jasper South

2.5 out of 5
1970 Hospitality Drive Jasper IN
Fully refundable
$121 nightly
The price is $136 total per night from Jul 26 to Jul 27
$136 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (588 reviews)
"Rooms were clean and a friendly staff."

Reviewed on Jul 1, 2026

Comfort Inn Jasper South
Fairfield Inn & Suites Jasper

Fairfield Inn & Suites Jasper

3 out of 5
333 River Centre Landing Jasper IN
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $178 total per night from Aug 2 to Aug 3
$178 total
Aug 2 - Aug 3
Total with taxes and fees
9.2/10 Wonderful! (415 reviews)
"Rooms were nice, and great location."

Reviewed on Jun 30, 2026

Fairfield Inn & Suites Jasper
See all 51 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

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Frequently asked questions

How much does a Montgomery vacation package cost?
Offering excellent value package deals from $665 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.