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Top Winona hotels

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
$115 nightly
The price is $125 total per night from Aug 8 to Aug 9
$125 total
Aug 8 - Aug 9
Total includes 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 ...
"Quiet"

Reviewed on Jul 20, 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
$99 nightly
The price is $108 total per night from Jul 25 to Jul 26
$108 total
Jul 25 - Jul 26
Total includes 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 ...
"I like the price but I didn't like that they don't change the sheets the every day and they don't have air freshner in the rooms"

Reviewed on Jun 27, 2025

Americas Best Value Inn Winona
Comfort Inn & Suites Grenada

Comfort Inn & Suites Grenada

2.5 out of 5
255 Sw Frontage Rd, Grenada, MS
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $125 total per night from Jul 31 to Aug 1
$125 total
Jul 31 - Aug 1
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...
"Friendly staff and clean rooms"

Reviewed on Jul 21, 2025

Comfort Inn & Suites Grenada
OYO Hotel Grenada West

OYO Hotel Grenada West

2 out of 5
1451 Sunset Drive, Grenada, MS
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $79 total per night from Aug 3 to Aug 4
$79 total
Aug 3 - Aug 4
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A communal living room and laundry facilities are also provided.
"It was a very nice and clean"

Reviewed on Jul 20, 2025

OYO Hotel Grenada West
Baymont by Wyndham Grenada

Baymont by Wyndham Grenada

2.5 out of 5
1575 Jamison Drive, Grenada, MS
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $81 total per night from Aug 3 to Aug 4
$81 total
Aug 3 - Aug 4
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business ...
"Beds were too high for a short person with bad legs."

Reviewed on Jul 4, 2025

Baymont by Wyndham Grenada
Relax Inn & Suites

Relax Inn & Suites

2 out of 5
328 US-82, Winona, MS
$70 nightly
The price is $76 total per night from Jul 26 to Jul 27
$76 total
Jul 26 - Jul 27
Total includes 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 ...
"Enjoyed my stay!"

Reviewed on Dec 9, 2024

Relax Inn & Suites
Charming ranch style log cabin with AC in scenic Winona

Charming ranch style log cabin with AC in scenic Winona

Winona
$285 nightly
The price is $311 total per night from Jul 25 to Jul 26
$311 total
Jul 25 - Jul 26
Total includes taxes and fees
This vacation home features laundry facilities.
Scenery was excellent!
"First time staying in a cabin and was absolutely impressed! It was such a peaceful stay especially coming from being in the daily city life! David was awesome at communicating. Will be reserving again for sure!"

Reviewed on May 6, 2025

Charming ranch style log cabin with AC in scenic Winona
Charming 3-bedroom barn in quaint Winona with AC

Charming 3-bedroom barn in quaint Winona with AC

Winona
$400 nightly
The price is $436 total per night from Jul 25 to Jul 26
$436 total
Jul 25 - Jul 26
Total includes taxes and fees
This vacation home features laundry facilities.
Charming 3-bedroom barn in quaint Winona with AC
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
$172 nightly
The price is $187 total per night from Jul 25 to Jul 26
$187 total
Jul 25 - Jul 26
Total includes taxes and fees
Stay at this vacation home in Winona. Enjoy air conditioning. Popular attractions Winona Country Club and Montgomery County Performing Arts Center are located ...
Cabin
"This is a cute little rustic cabin. Chad was very friendly and open to suggestions due to being a first time host."

Reviewed on May 4, 2025

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

Cheap Winona hotels

Americas Best Value Inn Winona

Americas Best Value Inn Winona

301 SE Frontage Road, Winona, MS
$99 nightly
The price is $108 total per night from Jul 25 to Jul 26
$108 total
Jul 25 - Jul 26
Total includes taxes and fees
8/10 Very Good! (415 reviews)
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.

Winona Hotel & Travel Guide

Arranging a trip to Grenada and hoping to discover basic or more upscale hotels in Winona? There are a limited number of options which can be booked via Travelocity's destination page. You'll be able to book 2 hotels within 6 miles (10 kilometers) of its central area.

Winona's city heart is a brisk walk from Travelocity-listed lodgings like Holiday Inn Express and Suites Winona North and Americas Best Value Inn & Suites.

Thinking of checking out more of the rivers and wetlands this area offers? Why not have some extra nights in some of the other areas of Northwest - Delta Region? You could see local diverse places of interest or have a go at mountain biking and horse riding and afterwards make a booking for a local Travelocity-registered lodging.

Located 25 miles (41 kilometers) to the west of Winona is Greenwood, which is where visitors can find various accommodation options. The Comfort Suites Greenwood and Holiday Inn Express & Suites - Greenwood are a few of the Travelocity-registered options here.

If sport is your passion, stop by C.M. Tad Smith Coliseum, which you will find 60 miles (100 kilometers) to the north of Winona. Travelers who enjoy the convenience of checking in to a room in the area, make a reservation in the Super 8 Oxford Ms or Quality Inn & Suites.

Why not look up Travelocity's complete Winona travel guide to explore the great cultural and scenic attractions that this area boasts.

Top reasons for your vacation to Winona

  • Outdoor Activities: Winona offers a range of outdoor activities, including exploring museums, historic sites, and spending a day by Lake Winona.
  • Small Town Charm: Experience the charm of small-town Winona by strolling through the picturesque downtown area and exploring local shops.
  • Baseball Excitement: Catch a game at the local stadium and cheer on the team for an exciting baseball experience.
  • Budget-Friendly Options: Enjoy budget-friendly outdoor excursions such as golf courses and hiking trails in Winona.
  • Family-Friendly Restaurants: There are plenty of family-friendly restaurants in Winona to refuel after a day of exploring and activities.

Find your favorite hotels in Winona

If you're planning an outdoor vacation in Winona, Mississippi, you'll find a range of hotel accommodations to choose from. Whether you're looking for a top hotel with luxurious amenities or a cozy pet-friendly option, there are options available to suit your needs. These accommodations provide a comfortable stay for you and your family, allowing you to explore the outdoor attractions and enjoy your vacation to the fullest.

Hotel nameTypeStarsDescription
Holiday Inn Express and Suites Winona North, an IHG HotelHotel2.5This 2.5-star hotel is a great option for your outdoor vacation. With its close proximity to the countryside, you can enjoy the beautiful scenery and outdoor activities. The hotel also offers a fitness center and sports facilities for those looking to stay active. After a day of exploring, you can relax by the outdoor pool or catch a baseball game. Plus, they offer free breakfast and pet-friendly accommodations, making it a convenient and welcoming choice for your family.
Americas Best Value Inn WinonaMotel2.0If you're looking for a budget-friendly option, this 2.0-star motel is a good choice. It is conveniently located near the countryside, offering opportunities for outdoor activities. The motel features an outdoor pool and offers free breakfast, making it suitable for families. They also have laundry facilities and are known for their friendly staff. With its proximity to excursions and its family-friendly atmosphere, Americas Best Value Inn Winona is a practical option for your outdoor vacation.
Relax Inn & SuitesMotel2.0This 2.0-star motel is another budget-friendly option for your outdoor vacation. It is known for its family-friendly atmosphere and friendly staff. With its proximity to baseball games and excursions, there are plenty of activities to keep you entertained. The motel also offers amenities such as coffee, dining options, and a golf course nearby. If you're looking to experience a small town atmosphere while staying on a budget, Relax Inn & Suites is a good choice for your outdoor vacation.

Explore the best activities and sights in Winona

Winona, Mississippi is a great destination for a family outdoor vacation. With its friendly people and small town charm, there are plenty of activities to keep everyone entertained. Explore the many museums and historic places, or enjoy a day by Lake Winona. For a fun shopping experience, check out the local antique stores. And when it's time to refuel, there are a variety of family-friendly restaurants to choose from. Whether you're into golf, baseball, or just want to relax in nature, Winona has something for everyone.

  1. Winona Country Club: The Winona Country Club offers a luxurious experience with its friendly members and picturesque golf course. Enjoy a cup of coffee while taking in the scenic views of the green fairways. If you're a baseball fan, catch a game at the club's baseball field. For those seeking adventure, the club organizes exciting excursions. With its budget-friendly options, it's a great place to unwind in a small town atmosphere. Whether you're into sports or looking to do some business networking, Winona Country Club has something for everyone. Don't forget to dine at their exquisite restaurant for a truly memorable experience.
  2. Montgomery County Performing Arts Center: Immerse yourself in culture and entertainment at the Montgomery County Performing Arts Center. This friendly venue offers a cozy atmosphere to enjoy a cup of coffee before or after a show. From theater performances to baseball tournaments, there's always something happening here. The center also offers budget-friendly options for those looking to experience the arts. Located in a charming small town, it provides a perfect setting for a romantic date night or a fun family outing. Whether you're a sports fan or a business traveler, the Montgomery County Performing Arts Center is a must-visit destination for a unique and memorable experience.

Where to stay in Winona

Experience the charm of small-town Winona, Mississippi, on your outdoor vacation. Explore the picturesque downtown area with its friendly people and local shops, where you can grab a cup of coffee and immerse yourself in the relaxed vibe. For baseball enthusiasts, catch a game at the local stadium and cheer on the team. If you're looking for outdoor excursions, Winona offers budget-friendly options like golf courses and hiking trails. Whether you're planning a romantic getaway or a family adventure, Winona has lots of places to explore and enjoy.

  1. Grenada: Grenada is a charming city located 20.3 miles away from Winona. It offers a unique experience with its delightful dining options, family-friendly atmosphere, cozy cafes, and vibrant shopping scene. The city is also known for its beautiful gardens and picturesque river, perfect for outdoor activities like sailing. Visitors can explore magnificent temples and admire historic monuments, including a stunning cathedral. Grenada is a great choice for an outdoor vacation with your family, as it combines cultural attractions with natural beauty.
  2. Kosciusko: Located 30.4 miles away from Winona, Kosciusko is a popular city known for its excellent hunting and biking opportunities. Families can also enjoy wildlife encounters and play golf in the city's scenic surroundings. Kosciusko offers exciting excursions and live music events, providing entertainment for all ages. The city's churches and cathedral showcase its rich religious heritage, while its natural parks offer a serene escape into nature. Kosciusko is a fantastic destination for an outdoor vacation, offering a range of activities that cater to different interests.
  3. Durant: Just 29.0 miles away from Winona, Durant is a charming city worth visiting. While specific unique experiences and local affinities for outdoor vacations were not mentioned, Durant offers a tranquil atmosphere and proximity to other exciting cities in the region. It can serve as a convenient base for exploring the surrounding areas and enjoying the natural beauty of Mississippi.

Best times to go to Winona

The travel seasons of Winona

Trips to Winona show no change in popularity throughout the year. The peak season to visit is from May to July, with June being the highest month. Off-peak season starts from October to December, and November sees the least travelers.

Winona has something in store for you whenever you visit. January is the coldest month of the year, while July is hottest, with average temperatures up to 80.8 degrees Fahrenheit. The wettest month in Winona is March, so pack accordingly.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationcloud iconCloudiness
January43.7°F (6.5°C)Light RainMostly Sunny
February47.7°F (8.7°C)Light RainMostly Sunny
March55.6°F (13.1°C)Light RainMostly Sunny
April62.6°F (17.0°C)Light RainMostly Sunny
May71.1°F (21.7°C)Light RainMostly Sunny
June78.8°F (26.0°C)Light RainMostly Sunny
July80.8°F (27.1°C)Light RainMostly Sunny
August80.2°F (26.8°C)Light RainMostly Sunny
September75.6°F (24.2°C)Light RainMostly Sunny
October65.1°F (18.4°C)Light RainMostly Sunny
November53.4°F (11.9°C)Light RainMostly Sunny
December48.0°F (8.9°C)Light RainMostly Sunny

Food and dining in Winona

When visiting Winona, Mississippi, you must try the local cuisine. One popular restaurant in the area is Pizza Inn, a moderately rated pizzeria that is highly popular among locals and travelers alike. If you're looking for more options, there are several other eateries to explore. For senior citizens or those seeking upscale dining experiences, Green Mill Restaurant is a great choice. Additionally, many restaurants are conveniently located near the intersection of the highway, making it easy to find a delicious meal during your vacation in Winona.

How do I find a great hotel with Travelocity?

Ensure your entire crew has an unforgettable vacation. Utilize our family-friendly badge to find hotels that offer special amenities for children. Our custom filters allow you to refine your search to hotels near popular attractions, with enhanced cleaning protocols, and within your budget. Trust our reliable online travel platform to make your trip planning a breeze.

Why should I book with Travelocity?

Conference calls, to-do lists and, of course, football practice. Busy lives and packed schedules call for trips that are hassle-free. Our aim is to provide stress-free travel every time you and your family book with us so that you can spend less time worrying and more time making cherished memories. In pursuit of this, we will assist you in finding and organizing your perfect trip, along with offering transparent pricing and reliable reviews, as well as 24/7 guaranteed customer support before, during, and after your vacation.

How can I save money on my trip to Winona?

If you're looking to save money on your trip to Winona, Mississippi, consider visiting during the less popular season of October-December. Bundle your flights, hotel, and car bookings together to take advantage of discounted prices. While in Winona, enjoy the three inexpensive local affinities of friendly people, budget-friendly dining options, and the small-town charm. Take the opportunity to explore the family-friendly attractions, sip on delicious coffee, and maybe even catch a baseball game.

Frequently asked questions

What are the top kid-friendly hotels in Winona?
Take some of the worries out of traveling with kids by opting for a family-friendly Winona hotel. From special amenities to services that bring a smile, these stays offer perks that'll make your getaway run smoothly: Relax Inn & Suites will help make your getaway the best one yet. It offers a range of nice little touches, such as front desk services and housekeeping services. Alternatively, spend your Winona break at Americas Best Value Inn Winona. Make the most of complimentary breakfast, a swimming pool and more here.
Where can I find cheap hotels in Winona?
At Travelocity you'll find really nice hotels in Winona at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winona rather than in Winona. We may find you even better rates, too.
How do I find the best Winona hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winona then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winona?
The cheapest hotel in Winona is $76. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winona?
There are 65 hotels in Winona on Travelocity.
What are the best hotels in Winona?
Winona has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winona for you!
When is the best time to visit Winona?
If you want the joy of a fun-filled trip in peak season, visit Winona during May, September and October. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Winona?
Based on historic data is usually the cheapest month to visit Winona. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winona?
There are multiple hotels in Winona that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winona. We have plenty of kid-friendly hotels in Winona to choose from on Travelocity!
Why book a hotel in Winona through Travelocity?
Because we have the top hotels in Winona! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winona on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winona hotel reviews by fellow wanderers