Montgomery Vacation Packages

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Top Montgomery Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Best Budget Inn

Best Budget Inn

2.5 out of 5
Price was CA $1,005, price is now CA $961 per person
CA $961
per person
Oct 23 - Oct 26
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Evansville (EVV)
5.2/10 (240 reviews)
When I first pulled in, the hotel itself gave off bad vibes, doors opening directly outdoors, each room having an outside chair and a small bucket for cigarettes (I don't smoke for the record) and it just looked like one of those cheap motels people might stay in for an extended period when they don't have a lot of options. When I first got into my room, I was nervous about what I was going to see. But it was clean, the WiFi was strong, TV had plenty of channels, it had a large refrigerator, the bed was comfortable, this was a great room! The only downside was the breakfast options. Because the tables were right up against the windows, I decided to take what I wanted back to my room, rather than sit where I'd exposed to the sun's heat. Not too bad of a place

Reviewed on Aug. 11, 2025

Residence Inn by Marriott Evansville East

Residence Inn by Marriott Evansville East

3 out of 5
Price was CA $1,091, price is now CA $1,022 per person
CA $1,022
per person
Oct 23 - Oct 26
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Evansville (EVV)
8.6/10 Excellent! (496 reviews)
the breakfast was absolutely amazing probably the best we've ever had as far as complimentary. the staff was also so nice and friendly and helpful!!

Reviewed on Aug. 20, 2025

Envi Boutique Hotel

Envi Boutique Hotel

4 out of 5
Price was CA $1,104, price is now CA $1,050 per person
CA $1,050
per person
Oct 23 - Oct 26
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Evansville (EVV)
8/10 Very Good! (259 reviews)
Okay the hotel is great besides the screen yelling at me every time I walk into the lobby, like no u can’t help me because I want a remote, towel, soap etc just zip it over there but besides hearing voices when entering the lobby 5 stars

Reviewed on Aug. 22, 2025

Howard Johnson by Wyndham Evansville East

Howard Johnson by Wyndham Evansville East

2.5 out of 5
Price was CA $1,056, price is now CA $1,012 per person
CA $1,012
per person
Oct 23 - Oct 26
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Evansville (EVV)
8.2/10 Very Good! (1,000 reviews)
Std quality, comfortable clean

Reviewed on Aug. 19, 2025

Ramada by Wyndham Tell City

Ramada by Wyndham Tell City

2.5 out of 5
Price was CA $1,040, price is now CA $1,000 per person
CA $1,000
per person
Oct 23 - Oct 26
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Evansville (EVV)
7.4/10 Good! (533 reviews)
Convenient and clean, pet friendly

Reviewed on Aug. 10, 2025

Ready to book your vacation to Montgomery?

 

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Montgomery Hotel Deals

Comfort Inn

Comfort Inn

2.5 out of 5
1970 Hospitality Drive, Jasper, IN
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Sep 3 to Sep 4
CA $128
CA $144 total
Sep 3 - Sep 4
includes taxes & fees
9/10 Wonderful! (503 reviews)
"We stayed at this hotel during a summer weekend at Holiday World. The staff was wonderful, and the indoor pool was a great addition to keep the kids content. The bed was very comfortable, and the water was hot. Good/hot breakfast served daily."

Reviewed on Aug. 15, 2025

Comfort Inn
Clarion Pointe

Clarion Pointe

2.5 out of 5
272 Brucke Strasse, Jasper, IN
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Sep 14 to Sep 15
CA $110
CA $123 total
Sep 14 - Sep 15
includes taxes & fees
8.8/10 Excellent! (148 reviews)
"Everything was very good. The bathroom toilet was the height of one from a kindergarten facility. Never seen a hotel toilet that height."

Reviewed on Aug. 24, 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
The price is CA $172 per night from Sep 7 to Sep 8
CA $172
CA $199 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very Good! (625 reviews)
"Very easy check in… Very nice people for a small town hotel with great amenities. Breakfast room was awesome. They even had a pool. I was just traveling for business through here. And this was a very nice hotel to stay in. I Will definitely come back when in town"

Reviewed on Aug. 19, 2025

Baymont by Wyndham Washington
See all 38 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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Montgomery vacation package cost?
Offering great value package deals from CA $961 on Expedia, you'll be surprised at how little a vacation to Montgomery costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Montgomery?
If you're looking to book a cheap Montgomery vacation package, consider visiting in January, February and November. You're likely to find lower rates on hotels and airfares during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Montgomery?
With a well-planned itinerary, you can easily visit the most popular Montgomery attractions in a few days. But if you prefer to discover hidden spots or go on day tours, think about booking your Montgomery vacation for longer.
How to find the best Montgomery package deals?
Landing a cheap Montgomery package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply some filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Montgomery package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Montgomery vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations separately. Better still, you can tailor your Montgomery trip to fit your exact needs. Choose 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're planning a spontaneous Montgomery vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Montgomery?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Montgomery.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and food to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Montgomery.
  3. Work out your trip length: Think about how long you'd like to spend discovering Montgomery. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a tailored Montgomery vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.