Winona Holiday Rentals from AU$227: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Winona has to offer?

The Hen House Retreat - A Comfortable Place to Roost : This holiday home rental outside of Winona is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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Our top choices for Winona holiday rentals

A modern apartment with a staircase, a dining area, and a living space.

1. Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

Winona

Mainul

includes taxes & fees

17 Sept - 18 Sept

A patio with two chairs and a table, a fire pit, a wooden fence, and a shed in the background.

2. Parkside Pet Friendly Bungalow

Winona

Mary T.

includes taxes & fees

30 Sept - 1 Oct

A two-story house with a wooden staircase leading to a yellow door, a brick wall, and a window with a white frame.

3. Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons

Historic Downtown Winona

Amy B.

includes taxes & fees

28 Sept - 29 Sept

A living room with a television, sofa, coffee table, and shelves with decorative items.

4. Vintage Lustron Home Piece of History

Minnesota City

Jocelyn R.

includes taxes & fees

23 Sept - 24 Sept

A spacious living room with a red sofa, a white coffee table, and a fireplace.

5. Great River Road - Victorian Historic Home (1898)

Fountain City

amy r.

includes taxes & fees

22 Sept - 23 Sept

A wooden deck with a bench, a white door, and hanging flower baskets.

6. The Bungaleau 1 Bedroom House In Cute Rivertown

Downtown Trempealeau

Lisa C.

includes taxes & fees

18 Sept - 19 Sept

A dining area with a wooden table and chairs, a kitchen with white cabinets, and two paintings on the wall.

7. The Chateau on Butterfly Trail - 6 Bdrm Retreat

Fountain City

Kathy P.

includes taxes & fees

17 Sept - 18 Sept

A bedroom with a bed, bedside table, lamp, and a view of the adjacent room through a wooden-framed door.

8. Spacious 2-bedroom loft above the International Owl Center in Houston, MN

Houston

Nikki W.

includes taxes & fees

17 Sept - 18 Sept

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Top Winona Hotel Reviews

Stoney Creek Hotel La Crosse - Onalaska

10/10 Excellent

"The king room with jacuzzi was amazing"

The Plaza Hotel & Suites Winona

8/10 Good

"I had two separate reservations (had issues editing original & added a 2nd night thru a separate booking - exact same room type). Upon check-in, the desk clerk said we'd have to check out in the morning & check back in later in the afternoon. Not an option for football parents: check-in/out time during game & festivities. The clerk was less than friendly about it & said I would just have to talk to the manager in the morning. So, I did - she was GREAT!! Took care of it in minutes. When the original clerk was back, I stopped back & let her know we were all good - only for her to turn her nose up at me & be so dismissive. Terrible customer service. (The manager, again: AWESOME & I saw her hustling - working so hard & very attentive to details). Tub drain was very slow; inches of water within moments of starting shower. Given issues at check-in, we opted to just deal with it vs call maintenance & run the risk of losing our room. At checkout, I let the young man at the desk know but he never even wrote it down. So, hopefully room 111 is fixed for the next person. We've stayed at the Plaza several times over the past 4+ years and enjoy the convenience of the onsite restaurant (good food, great staff!). When not too busy, the pool & hot tub are great amenities (unless overrun by kids). Breakfast is Jimmy Dean sandwiches. Hotel is aging, needs a deep cleaning, refresh with paint. Simple touches to improve go a long way. Ultimately, we know what to expect upon staying here."

Express Suites Riverport Inn & Suites

8/10 Good

"Staff were extremely friendly and responsive. Clean room, had a hot breakfast which we didn’t sample-the only complaint here is the bed left my husband and I needing the chiropractor. Also the pillows felt like sleeping on a pile of cotton balls. If you’re young and still have a strong back you’ll be fine."

Super 8 by Wyndham Winona MN

8/10 Good

"You get what you paid for. I went in with no expectations and it was worth it for my family during our 2 night stay, I booked my reservation very early so the price wasn’t ridiculously high. We just needed a place to sleep so we didn’t need anything fancy. Right when you walk in there is an odd smell but you don’t smell it in the room, a lot of their towels had stains so we had to ask a few times and their pillows are very flat. The plus is that it’s a walking distance to the bluff for hiking! Staffs were friendly and plenty of parking spots."

Alexander Mansion Bed and Breakfast

10/10 Excellent

"Staying at Alexander Mansion is an experience in elegance, graciousness and a thoughtful approach to hospitality. The multi course breakfast hosted by Richard is an event in and of itself and resulted in enjoyable social interactions with staff and other guests! We have stayed there twice and hope to continue to return!"

Find out more about Winona

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Winona holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as AU$227 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find holiday rentals in Winona?

Yes, there are holiday rentals in Winona close to Valencia Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. The riverfront and museums are just a few reasons why tourists like Winona. Make sure you have time to check out the gardens and churches during your trip.

What are some of the best holiday rentals that Winona has to offer?

The Hen House Retreat - A Comfortable Place to Roost: This holiday home rental outside of Winona is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Winona?

Expedia has 13 holiday rentals for your stay in Winona.

What can I see and do in Winona?

Enjoy the outdoors at Lake Park and Sugar Loaf Bluff, or simply take in cultural attractions like Minnesota Marine Art Museum and Winona County Historical Society. While here, Great River Bluffs State Park and Mississippi River are other places worth a visit.

What are holiday rentals like in Winona?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winona. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for families.

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Check prices for these dates

Our top choices for Winona holiday rentals

1. Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

2. Parkside Pet Friendly Bungalow

3. Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons

4. Vintage Lustron Home Piece of History

5. Great River Road - Victorian Historic Home (1898)

6. The Bungaleau 1 Bedroom House In Cute Rivertown

7. The Chateau on Butterfly Trail - 6 Bdrm Retreat

8. Spacious 2-bedroom loft above the International Owl Center in Houston, MN

9. Tamarack Point Homestead

10. NEW Mississippi Riverfront Sunset House - family, friends & river come together

11. Ridgetop Retreat Tiny Home, Dakota MN

12. River Eagle Cabin #1 w/ Screened Porch & Fire Pit

13. Tiny Treehouse Cabin | Bluff Woodlands #2

14. Big River Escape Coyote Camper #1

15. The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air

16. Badger Cabin w/ Lofts, Fireplace & WiFi

17. Riverfront Cabin with Private Dock

18. Riverview, 5BR, Hot tub, Fireplace, Arcade Game

19. Tiny Treehouse Cabin | Bluff Woodlands #3

20. Three Treehouse Cabins in the Bluff Woodlands

Find holiday rentals that suit your style

Top Winona Hotel Reviews

Stoney Creek Hotel La Crosse - Onalaska

Gundersen Hotel & Suites

The Plaza Hotel & Suites Winona

Pearl Street Hotel & Suites

Express Suites Riverport Inn & Suites

Super 8 by Wyndham Winona MN

The Charmant Hotel

Creekside Cabin Getaway

Alexander Mansion Bed and Breakfast

Find out more about Winona

Frequently asked questions

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