Montgomery Vacations from $560

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The Latest Montgomery vacation packages

Price found within the past 48 hours. Click for updated prices.
Comfort Inn Evansville East

Comfort Inn Evansville East

2.5 out of 5
Price was $623, price is now $560 per person
$560
per person
Apr 2 - Apr 5
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) to Evansville (EVV)
7.8/10 Good! (825 reviews)
Breakfast was great and staff very nice. The building needs to be updated but for the price, our stay was fine.

Reviewed on Nov 10, 2025

Wingate by Wyndham Owensboro

Wingate by Wyndham Owensboro

2.5 out of 5
Price was $674, price is now $601 per person
$601
per person
Apr 2 - Apr 5
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) to Evansville (EVV)
7.4/10 Good! (763 reviews)
Walking in after a long day I was met with a clean lobby, a clean smell and wonderful staff. All of my questions were answered regarding things around the area and the hotel but he was so sweet. I will give a heads up, they are renovating!! Everything is nice and clean and new but there was a couple hiccups in the room that come with renovations and finding the kinks along the way. Nothing that was trip ending, just things that make you giggle. Staff was made aware and they were so sweet and apologized when it wasn’t necessary. Will be coming back on our next trip to the area for sure!

Reviewed on Dec 7, 2025

Residence Inn by Marriott Evansville East

Residence Inn by Marriott Evansville East

3 out of 5
Price was $670, price is now $604 per person
$604
per person
Apr 2 - Apr 5
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) to Evansville (EVV)
8.6/10 Excellent! (508 reviews)
Our preferred choice to stay when traveling to Evansville. Pleasant stay with great customer service. Nice updated renovations!

Reviewed on Jan 5, 2026

Envi Boutique Hotel Henderson-Evansville South

Envi Boutique Hotel Henderson-Evansville South

3 out of 5
Price was $648, price is now $594 per person
$594
per person
Apr 2 - Apr 5
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) to Evansville (EVV)
8/10 Very Good! (280 reviews)
From the outside, I would call this a Motel rather than a Hotel. But inside, the rooms are updated and clean. We stayed four nights while I was visiting my family in Henderson. It is honestly so much better than I had anticipated based on how it looks from the outside.

Reviewed on Jan 1, 2026

Quality Inn & Suites Rockport - Owensboro North (GOLD AWARD WINNER)

Quality Inn & Suites Rockport - Owensboro North (GOLD AWARD WINNER)

2.5 out of 5
Price was $673, price is now $618 per person
$618
per person
Apr 2 - Apr 5
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) to Evansville (EVV)
8.2/10 Very Good! (396 reviews)
Owners and workers were top quality, super nice and helpful. Rooms were nicely updated, except for carpet and smell. That ruined it all for me. Only place near Holiday world that looked ok. Cereal Was stale at breakfast.

Reviewed on Oct 19, 2025

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Montgomery Hotel Deals

Hampton Inn Jasper

Hampton Inn Jasper

2.5 out of 5
355 3rd Ave Jasper IN
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $111 total per night from Feb 13 to Feb 14
$111 total
Feb 13 - Feb 14
Total with taxes and fees
9.6/10 Exceptional! (273 reviews)
Room was cleaned, cozy, comfy and relaxing.

Reviewed on Dec 22, 2025

Hampton Inn Jasper
Clarion Pointe

Clarion Pointe

2.5 out of 5
272 Brucke Strasse Jasper IN
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $80 total per night from Jan 25 to Jan 26
$80 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (201 reviews)
Staff was very friendly. The hotel was clean and comfortable. We would definitely stay here again.

Reviewed on Dec 7, 2025

Clarion Pointe
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
$94 nightly
The price is $110 total per night from Jan 17 to Jan 18
$110 total
Jan 17 - Jan 18
Total with taxes and fees
8/10 Very Good! (663 reviews)
The hotel was clean, but you can definitely tell it’s an older facility. The staff was very nice and helpful. The breakfast was average. It’s a typical hotel breakfast but the breakfast space was very clean and the service to the breakfast station was very attentive. I mean overall for the small ...

Reviewed on Jan 6, 2026

Baymont by Wyndham Washington
See all 44 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 $560 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.