Montgomery County Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Martin Tucker

Top hotels in Montgomery County

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 2.921.964 ₫ per night from 16 Jan to 17 Jan
2.921.964 ₫
3.184.941 ₫ total
16 Jan - 17 Jan 2026
includes taxes & fees
8.2/10 Very Good! (674 reviews)
Clean comfortable room. Check in was great. Very welcoming.

Reviewed on 14 Dec 2025

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 2.606.076 ₫ per night from 20 Dec to 21 Dec
2.606.076 ₫
2.840.622 ₫ total
20 Dec - 21 Dec
includes taxes & fees
8/10 Very Good! (457 reviews)
Room was clean and the beds were great

Reviewed on 3 Dec 2025

Americas Best Value Inn Winona
Relax Inn & Suites

Relax Inn & Suites

2 out of 5
328 US-82 Winona MS
5.8/10 (52 reviews)
Cheap place to stay. We had to check in after hours. We had a hard time getting someone to show up at the front desk. When speaking to the woman there was a communication problem; English is not her first language. There were no visible bed bugs, no roaches. We always check! The remote they gave ...

Reviewed on 3 Dec 2025

Get rates
Relax Inn & Suites
See all 60 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.

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 1null000null000 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.

Explore a world of travel with Expedia