Deals on vacations and trips to Winona

Save when you book Winona package deals

Choose two or more items and save on your trip:

Top Winona hotels 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
Free Cancellation
$102 nightly
The price is $111 total per night
$111 total
Aug 9 - Aug 10
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.
Pool
Breakfast included
Americas Best Value Inn Winona

Americas Best Value Inn Winona

2 out of 5
301 SE Frontage Road Winona MS
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $108 total per night
$108 total
Jul 13 - Jul 14
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.
Pool
Breakfast included
Relax Inn & Suites

Relax Inn & Suites

2 out of 5
328 US-82 Winona MS
$70 nightly
The price is $76 total per night
$76 total
Jul 13 - Jul 14
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.
Parking included
Free WiFi
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

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

Winona MS
$172 nightly
The price is $187 total per night
$187 total
Jul 13 - Jul 14
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.
Kitchen
Air conditioning
Charming 3-bedroom barn in quaint Winona with AC

Charming 3-bedroom barn in quaint Winona with AC

Winona MS
$399 nightly
The price is $435 total per night
$435 total
Jul 22 - Jul 23
Total with taxes and fees
This vacation home features laundry facilities.
Kitchen
Washer
Charming ranch style log cabin with AC in scenic Winona

Charming ranch style log cabin with AC in scenic Winona

Winona MS
$285 nightly
The price is $311 total per night
$311 total
Jul 13 - Jul 14
Total with taxes and fees
This cabin features laundry facilities.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Winona
View all properties
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.

Stay near popular Winona 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 theater scene while you're in the area.
See properties

Frequently asked questions

How much are vacation packages to Winona?
You can get a great flight and hotel bundle from just . With a Travelocity vacation package, a getaway to Winona has never looked so good! Save your time and money and get an early start with packing your suitcases.
How long should my Winona vacation be?
Many visitors pack their suitcase and explore the sights of Winona for an average of 2 nights. That's a great guide, but you're not bound by it. Whether you only stay a few nights to see the famous attractions or linger a while to uncover off-the-beaten-path gems, an epic adventure awaits.
Where can I get the best vacation package deals for Winona?
It's simple — head to Travelocity. With no less than 400 partner airlines and 1,000,000 worldwide properties, it's easy to put together a Winona package deal that ticks all your boxes.
Why should I book my Winona vacation bundle via Travelocity?
We take the stress out of travel planning. Whether you're looking for an amazing new place to uncover or want to make sure you get the best deal around, we've got your back. Our 24/7 support, high-quality service and Price Match Guarantee mean you can book with confidence with Travelocity.
Can I save on my Winona car rental if I bundle it with hotels and flights?
Combining your car, flight and hotel into a Winona vacation package is the easiest way to land the best deal. Plus, having your own car rental gives you absolute freedom to make your way to all those landmarks you're itching to see. Situated 120 mi from Winona, Orpheum Theatre is one attraction that should feature on your itinerary. Put together a driving playlist and make a day trip of it.
What is there to do in Winona?
Montgomery County Performing Arts Center deserves a spot on your to-do list. Once you've crossed off this renowned attraction, amble through the streets of Winona and find out what makes this fantastic city tick.
Where should I stay when visiting Winona?
The Holiday Inn Express and Suites Winona North, an IHG Hotel is popular with many visitors. Book soon to avoid missing out.

Photos of local treasures

Browse Winona vacation photos for more inspiration

A brick building with the inscription "WINONA" and an arched window.