Winona Vacation Packages

Save when you book Winona package deals

Choose two or more items and save on your trip:

Top Winona hotel deals

Holiday Inn Express and Suites Winona North, an IHG Hotel

Holiday Inn Express and Suites Winona North, an IHG Hotel

2.5 out of 5
413 SE Frontage Road, Winona, MS
Free Cancellation
The price is $142 per night
$142
per night
May 31 - Jun 1
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

Americas Best Value Inn Winona

2 out of 5
301 SE Frontage Road, Winona, MS
Free Cancellation
Reserve now, pay when you stay
The price is $95 per night
$95
per night
May 27 - May 28
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.
Breakfast included
Pool
Relax Inn & Suites

Relax Inn & Suites

2 out of 5
328 US-82, Winona, MS
The price is $70 per night
$70
per night
May 27 - May 28
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.
Comfort Inn & Suites Grenada

Comfort Inn & Suites Grenada

2.5 out of 5
255 Sw Frontage Rd, Grenada, MS
Free Cancellation
Reserve now, pay when you stay
The price is $104 per night
$104
per night
Jun 2 - Jun 3
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. A computer station, dry cleaning, and laundry facilities are also on offer.
Pet friendly
Breakfast included
Baymont by Wyndham Grenada

Baymont by Wyndham Grenada

2.5 out of 5
1575 Jamison Drive, Grenada, MS
Free Cancellation
Reserve now, pay when you stay
The price is $72 per night
$72
per night
Jun 2 - Jun 3
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's a 24-hour gym on site, and a 24-hour front desk and express check-out are also provided.
SureStay Plus Hotel by Best Western Greenwood

SureStay Plus Hotel by Best Western Greenwood

2.5 out of 5
635 Highway 82 W, Greenwood, MS
Free Cancellation
Reserve now, pay when you stay
The price is $139 per night
$139
per night
Jun 2 - Jun 3
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
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.

Popular places to visit in Winona

Image for Winona Country Club

Winona Country Club

4.5/5(4 reviews)

Enjoy a round of golf in Winona at Winona Country Club.

Winona Country Club
Image for Montgomery County Performing Arts Center

Montgomery County Performing Arts Center

4/5(4 reviews)

You can get tickets for a performance at Montgomery County Performing Arts Center on your trip to Winona. Take in the theater scene while you're in the area.

Montgomery County Performing Arts Center
Image for Middleton Cemetery

Middleton Cemetery

4/5(6 reviews)

Enjoy a stop at Middleton Cemetery, a landmark worth seeing in Winona. Take in the theater scene while you're in the area.

Middleton Cemetery

Photos of local treasures

Frequently asked questions

How much are vacation packages to Winona?
With vacation packages being sold from just , there’s no need to empty your piggy bank for your getaway to Winona. Travelocity is here to help. Combine experiences, hotels and flights into a package and land impressive discounts. The more you book, the greater the savings.
How long should my Winona vacation be?
Around 2 nights is what many visitors book for their Winona vacation. That’s a good guide, but there’s loads more to uncover if you give yourself a few extra days.
Where can I get the best vacation package deals for Winona?
Walking away with a great package deal to Winona is a piece of cake with Travelocity. With 400 air carriers and 1,000,000 worldwide properties, you’re flush with choice when it comes to your hotels and flights.
Why should I book my Winona vacation bundle via Travelocity?
Nothing tops the peace of mind knowing you’ve just bagged the best deal around — that’s our Price Match Guarantee. Add to that our inspiring range of magical destinations and 24/7 team of customer service professionals and you’ve got the formula for an unforgettable vacation.
Can I save money on my Winona car rental if I combine it with hotels and flights?
Combining your car, flight and hotel into a Winona vacation package is an excellent way to score an amazing deal. Plus, having your own car rental gives you the freedom to make your way to all those big sights you’re itching to check out. Sitting 110 mi away from Winona, Graceland is one attraction that should be on your agenda. Put together a driving playlist and make a day trip of it.
What is the best time of year to go to Winona?
Vacation in and spend more money on awesome experiences, rather than your hotel room. This is the most cost-effective month to lock in a stay. Prices are highest in , so try to avoid this time if you’re on a tight budget. May, September and October are the tourist season months in Winona. You’ll need to book well in advance and be prepared to pay higher prices. November, December and January are the quietest months.
What is there to do in Winona?
There’s a certain kind of magic as you wander the streets of Winona. Winona Country Club and Montgomery County Performing Arts Center are just a couple of highlights that entice visitors to this wonderful city, so add them to your must-see list.
Where should I stay when visiting Winona?
Many visitors choose to check in to the Holiday Inn Express and Suites Winona North, an IHG Hotel. It’s sure to be a good base for your Winona getaway.