Montgomery County Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Montgomery County Vacation

Make organizing your next big adventure a piece of cake with a Montgomery County vacation package. Whether it's nature, history or something else entirely that lures you to this destination, our package deals will help you discover it all. A trip to Montgomery County offers so much to see and do. Not sure where to kick off your itinerary? Winona is one of the most popular cities to stay here. Stop dreaming and start packing, because your Montgomery County vacation is only a few clicks away with Expedia.

Montgomery County Hotel Deals

Holiday Inn Express and Suites Winona North by IHG

Holiday Inn Express and Suites Winona North by IHG

2.5 out of 5
413 SE Frontage Road Winona MS
Fully refundable
The price is CA $163 per night from Jun 21 to Jun 22
CA $163
CA $177 total
Jun 21 - Jun 22
includes taxes & fees
8.2/10 Very Good! (714 reviews)
"Breakfast was fresh with many choices. Staff attentive and friendly."

Reviewed on May 20, 2026

Holiday Inn Express and Suites Winona North by IHG
Americas Best Value Inn Winona

Americas Best Value Inn Winona

2 out of 5
301 SE Frontage Road Winona MS
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from May 30 to May 31
CA $136
CA $149 total
May 30 - May 31
includes taxes & fees
8/10 Very Good! (492 reviews)
"breakfast was ok. not very busy."

Reviewed on May 27, 2026

Americas Best Value Inn Winona
Relax Inn & Suites

Relax Inn & Suites

2 out of 5
328 US-82 Winona MS
The price is CA $87 per night from May 30 to May 31
CA $87
CA $95 total
May 30 - May 31
includes taxes & fees
Relax Inn & Suites
See all 77 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?
We make it simple to explore the world, with Montgomery County vacation packages starting from as low as . You'll have the flexibility to combine your favorite airlines, hotels and car rental. For the ultimate getaway, why not add a couple of experiences and tours to your itinerary?
How do I get a cheap travel package to Montgomery County?
If you love getting an amazing deal, bundle your bookings into a Montgomery County vacation package. Whether you need flights, hotels, rental cars or activities, you can browse and book everything in one place. You'll have plenty of choice at your fingertips as well. Expedia has more than 550 airlines and 1,000,000 hotels around the globe to choose from. Fly with who you want, stay where you like and save a bundle — now that's the ideal vacation!
What are the top hotels in Montgomery County?
If you're on your way to Winona, you can't go past Holiday Inn Express and Suites Winona North, an IHG Hotel and Americas Best Value Inn Winona. Both are great bases for discovering this vibrant Montgomery County city.
How far in advance should I book my Montgomery County vacation?
To score cheap prices, book as early as you can. Airlines usually release flight tickets, along with some of the lowest fares, around a year in advance. Hotels, experiences and car rental should also be booked well in advance to avoid disappointment. If you were hoping for a last-minute getaway in Montgomery County, there are always plenty of great deals on Expedia. Book something in today!
What does an Expedia Montgomery County travel package include?
Flights, rental cars and hotels, or any combination of them — it's totally up to you. Whether you're exploring Montgomery County with the entire family or traveling solo, there's a bundle to fit every budget and style. Once you've made your booking, why not add on some activities?
What should I know before booking a Montgomery County travel package?
You can save big by bundling your hotels, airfares and rental cars. Once you've created your package, you can add on sightseeing tours or experiences. Your next unforgettable vacation is only a few clicks away.
Can I choose my airline with a Montgomery County Expedia vacation package?
Yes, definitely. Expedia has over 550 airline partners to pick from across the world. With such a big range of choice, finding the ideal carrier to get you to Montgomery County will be a cinch.
If I'm not able to travel, can I cancel my Montgomery County vacation package?
Yes you can, and we're here to help. You may be able to cancel and rebook your Montgomery County vacation package for free if you booked in the last 24 hours. But you may be charged a fee by your airline, hotel or car rental company for older bookings. If life throws you a curveball, browse our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.