Montgomery County Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Montgomery County
Holiday Inn Express and Suites Winona North by IHG
413 SE Frontage Road Winona MS
S$145
27 Sept - 28 Sept
includes taxes & fees
8.2/10 Very good! (743 reviews)
"Clean room working a/c hot water nice size pool working exercising equipment hot breakfast... All the workers give you welcoming hospitality!!! What more can one ask for"
Reviewed on 7 Sept, 2026
Americas Best Value Inn Winona
301 SE Frontage Road Winona MS
Fully refundableReserve now, pay when you stay
S$136
9 Oct - 10 Oct
includes taxes & fees
Relax Inn & Suites
328 US-82 Winona MS
S$74
9 Oct - 10 Oct
includes taxes & fees
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.
Frequently asked questions
How much does a Montgomery County holiday package cost?
We make it simple to explore the world, with Montgomery County holiday packages starting from as low as . You'll have the flexibility to combine your favourite 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 holiday 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 holiday!
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 holiday?
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 travelling solo, there's a bundle to fit every budget and style. Once you've made your booking, why not add on some activities?
Can I choose my airline with a Montgomery County Expedia holiday 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 holiday package?
Yes you can, and we're here to help. You may be able to cancel and rebook your Montgomery County holiday 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.
Stay near popular Montgomery County attractions
Montgomery County Performing Arts Center
7.0/10 (20 reviews)
Enjoy an outing to Montgomery County Performing Arts Center during your stay in Winona. Take in the theatre scene while you're in the area.
Winona City Hall
After visiting Winona City Hall, make a plan to see the other sights and activities in Winona.
Tyler Holmes Memorial Hospital
If Tyler Holmes Memorial Hospital is what brings you to town, hopefully you'll have a chance to explore more of Winona.
Winona Country Club
6.4/10 (26 reviews)
Enjoy a round of golf in Winona at Winona Country Club.
Winona - Montgomery County Library
After visiting Winona - Montgomery County Library, make a plan to see the other sights and activities in Winona.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
