Montgomery County Vacation Packages 2026 from $563

Montgomery County flight + hotel vacation packages

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

The Grand Motel

$563

per person

May 22 - May 24

found 20 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Columbus (GTR)

Free WiFi in public areas is available at this motel. Take advantage of the free self parking.

Hyatt Place Columbus

$652

per person

May 22 - May 24

found 20 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Columbus (GTR)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like on-the-go breakfast and free self parking.

My Home at Columbus

$564

per person

May 22 - May 24

found 20 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Columbus (GTR)

This hotel features a coffee shop, laundry facilities, and free self parking. WiFi in public areas is free. A snack bar/deli is provided and the front desk is staffed around-the-clock.

Americas Best Value Inn West Point, MS

$601

per person

May 22 - May 24

found 20 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Columbus (GTR)

This hotel features a gym and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Days Inn by Wyndham Columbus

$572

per person

May 22 - May 24

found 20 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Columbus (GTR)

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and free newspapers.

Top Montgomery County hotels deals

Holiday Inn Express and Suites Winona North by IHG

413 SE Frontage Road Winona MS

Free Cancellation

$118 nightly

$129 total

May 17 - May 18

Total with taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Americas Best Value Inn Winona

301 SE Frontage Road Winona MS

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$108 total

Apr 21 - Apr 22

Total with taxes and fees

An outdoor pool is featured at this motel, along with free self parking. Enjoy the free continental breakfast each morning. A garden is provided and the front desk is staffed around-the-clock.

Relax Inn & Suites

328 US-82 Winona MS

$70 nightly

$76 total

Apr 21 - Apr 22

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Charming ranch style log cabin with AC in scenic Winona

Winona MS

$283 nightly

$308 total

Apr 21 - Apr 22

Total with taxes and fees

This cabin features laundry facilities.

Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

Winona MS

$171 nightly

$186 total

Apr 21 - Apr 22

Total with taxes and fees

Stay at this cabin in Winona. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Winona Country Club and Montgomery County Performing Arts Center are located nearby.

Charming 3-bedroom barn in quaint Winona with AC

Winona MS

$398 nightly

$434 total

Apr 21 - Apr 22

Total with taxes and fees

This vacation home features laundry facilities.

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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.

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Frequently asked questions

How much are vacation packages to Montgomery County?

Travelocity provides flight and hotel vacation packages from just $563. With such amazing bargains, you'll be saying hello to Montgomery County before long.

Where can I get the best vacation package deals for Montgomery County?

Travelocity can help you snap up a great Montgomery County package deal. With no less than 400 airlines and 1,000,000 properties worldwide, there's no doubt you'll be able to put together the perfect itinerary.

Why should I purchase my Montgomery County vacation package via Travelocity?

Because we believe in crafting special vacation experiences. From flights and hotels to car rentals and activities, everything is at your fingertips. Our customer support is available 24/7 to ensure you'll never roam alone. We also have an amazing Price Match Guarantee, so you can book your vacation knowing you've scored the best deal around.

Can I save money on my Montgomery County car rental if I book it with a hotel or flight?

Sure can. And our Montgomery County vacation packages are the best way to do it. With only a few clicks you can save money as well as time by booking everything in one place. Collect the keys to your rental car then set your own course. Searching for things to do? Throw some tours or experiences into your package and save on those too.

Which airport is best for Montgomery County?

Golden Triangle Regional Airport (GTR) is where most visitors to Montgomery County disembark the plane.

What is there to do in Montgomery County?

A must-see attraction you shouldn't miss in Montgomery County is Montgomery County Performing Arts Center. After you've been there, spend time connecting with locals and uncovering the character of this exciting destination.