Montgomery County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Your Montgomery County Vacation

Leave the planning up to us with a Montgomery County vacation package. With everything organized before you head off, the only thing left for you to do is relax and enjoy this destination's culture and charm. Not sure where to stay? Waynetown is one of the most popular cities to explore during a trip to Montgomery County. Expedia has flights, hotels, car rentals and more to help you curate your own customized Montgomery County vacation today.

Top Montgomery County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The village

The village

4 out of 5
Near Westside
Price was CA $1,393, price is now CA $1,250 per person
CA $1,250
per person
Jun 5 - Jun 7
found 4 hours ago
Roundtrip flight included
Saskatoon (YXE) to Indianapolis (IND)
7.8/10 Good! (45 reviews)
Would definitely stay again!

Reviewed on Mar 6, 2026

Spacious Duplex for 14 in Downtown

Spacious Duplex for 14 in Downtown

3 out of 5
Price was CA $1,692, price is now CA $1,506 per person
CA $1,506
per person
Jun 5 - Jun 7
found 4 hours ago
Roundtrip flight included
Saskatoon (YXE) to Indianapolis (IND)
No reviews
Bottleworks Hotel

Bottleworks Hotel

4.5 out of 5
Downtown Indianapolis
Price was CA $1,602, price is now CA $1,439 per person
CA $1,439
per person
Jun 5 - Jun 7
found 4 hours ago
Roundtrip flight included
Saskatoon (YXE) to Indianapolis (IND)
9.8/10 Exceptional! (1,834 reviews)
Loved the property, overall atmosphere of the area, and experience was amazing

Reviewed on Mar 9, 2026

Landing Incredible 1bd, Gym, Pool

Landing Incredible 1bd, Gym, Pool

3 out of 5
Near Northside
Price was CA $1,436, price is now CA $1,297 per person
CA $1,297
per person
Jun 5 - Jun 7
found 4 hours ago
Roundtrip flight included
Saskatoon (YXE) to Indianapolis (IND)
No reviews
Historic Pet-Friendly Home in Downtown

Historic Pet-Friendly Home in Downtown

3 out of 5
Price was CA $1,366, price is now CA $1,272 per person
CA $1,272
per person
Jun 5 - Jun 7
found 4 hours ago
Roundtrip flight included
Saskatoon (YXE) to Indianapolis (IND)
No reviews

The Annual Vacation Sale

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Montgomery County Hotel Deals

Holiday Inn Express Hotel & Suites Crawfordsville by IHG

Holiday Inn Express Hotel & Suites Crawfordsville by IHG

2.5 out of 5
2506 N. Lafayette Road Crawfordsville IN
Fully refundable
The price is CA $157 per night from Mar 29 to Mar 30
CA $157
CA $173 total
Mar 29 - Mar 30
includes taxes & fees
Holiday Inn Express Hotel & Suites Crawfordsville by IHG
Best Western Plus Crawfordsville Hotel

Best Western Plus Crawfordsville Hotel

2.5 out of 5
2600 Industrial Blvd Crawfordsville IN
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Mar 22 to Mar 23
CA $129
CA $142 total
Mar 22 - Mar 23
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
Fine breakfast

Reviewed on Mar 8, 2026

Best Western Plus Crawfordsville Hotel
Hampton Inn & Suites Crawfordsville

Hampton Inn & Suites Crawfordsville

2.5 out of 5
2895 Gandhi Drive Crawfordsville IN
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Mar 22 to Mar 23
CA $138
CA $152 total
Mar 22 - Mar 23
includes taxes & fees
9.2/10 Wonderful! (839 reviews)
Very clean, great staff, good breakfast options, & reasonably priced

Reviewed on Mar 8, 2026

Hampton Inn & Suites Crawfordsville
See all 397 properties in Montgomery County
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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Montgomery County vacation package cost?
Live it up in Montgomery County from just CA $1,250. We offer a wonderful selection of rental cars, hotels and flights to suit every budget and style. Land even more discounts when you add some activities or tours to your vacation package.
How do I get a cheap travel package to Montgomery County?
Bundle your flights and hotels with Expedia to save big on your next exciting adventure. With over 550 airlines and 1,000,000 hotel options around the globe, your Montgomery County vacation package can be customized exactly to suit your budget. With all those extra dollars, why not throw in a few interesting experiences and tours? It's an easy way to unlock even more savings. Your dream vacation in Montgomery County is closer than you thought!
What are the top hotels in Montgomery County?
Best Western Plus Crawfordsville Hotel and Holiday Inn Express Hotel & Suites Crawfordsville, an IHG Hotel know how to make their guests feel at home in Waveland. If you also plan to get to Waynetown, take a look at Comfort Inn and Super 8 by Wyndham Crawfordsville. Both are popular with travelers.
How far in advance should I book my Montgomery County vacation?
It all depends on the air carrier, but it's usually possible to compare international flights on Expedia nearly a year in advance. While it's generally recommended to book ahead of time, lucky travelers will occasionally score a cheaper seat just weeks before their intended journey.
What does an Expedia Montgomery County travel package include?
It all boils down to what sort of escape you want to have. Montgomery County vacation deals can include hotels, flights and car rentals. You can mix and match to find the bundle that suits your budget and style. You can also add on activities and experiences after you've booked to get even bigger discounts.
What should I know before booking a Montgomery County travel package?
You'll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and land fabulous discounts. Hotels aren't your only choice, though. We've got beachside condos, cabins in the mountains and everything in between!
Can I choose my airline with a Montgomery County Expedia vacation package?
With a vacation package, you're in charge. Whether you'd prefer to fly to Montgomery County in business or coach, simply select from the available airline options. Expedia has access to over 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Montgomery County vacation package?
Your situation can change without warning, so yes, you can. You may be able to cancel or alter your Montgomery County vacation package at no cost within 24 hours of booking. For bookings made more than 24 hours ago, you can still make the necessary changes, but your airline, hotel or car rental company may charge a fee. Need more information? Check out our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.