Winona Vacation Rentals from ￥14,453: Search Short-Term Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Winona vacation rentals

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

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

Historic Downtown Winona

Amy B.

￥32,817 total

includes taxes & fees

Nov 23 - Nov 24

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

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

Winona

Nicole H.

￥45,628 total

includes taxes & fees

Nov 9 - Nov 10

A round glass table with two wicker chairs, a bottle, and two glasses of red wine on a metal tray.

3. Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN

Winona

Ruth S.

￥69,416 total

includes taxes & fees

Nov 9 - Nov 10

A modern living room with a black door, a grey armchair, a sofa, and a lamp.

4. Parkside Pet Friendly Bungalow

Winona

Mary T.

￥39,268 total

includes taxes & fees

Nov 30 - Dec 1

A field of lavender with a path leading through it.

5. Tamarack Point Homestead

Arcadia

RICHARD

￥19,562 total

includes taxes & fees

Nov 24 - Nov 25

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

6. Vintage Lustron Home Piece of History

Minnesota City

Jocelyn R.

￥31,045 total

includes taxes & fees

Nov 16 - Nov 17

A wooden cabin with a porch, a door, and a small seating area with two chairs.

7. Tiny Treehouse Cabin | Bluff Woodlands #2

Elba

I.M l.

￥30,219 total

includes taxes & fees

Nov 10 - Nov 11

A cabin surrounded by dense forest, with a wooden deck and a hammock.

8. Tiny Treehouse Cabin | Bluff Woodlands #1

Elba

Paul T.

￥32,317 total

includes taxes & fees

Nov 9 - Nov 10

A rustic wooden pavilion with picnic tables, surrounded by a gravel area and grassy lawn.

9. Cozy River Cabin w/ Loft & Screened Porch

Buffalo City

John S.

￥23,527 total

includes taxes & fees

Dec 1 - Dec 2

A two-story house with a balcony, surrounded by a grassy field and trees, with a forested hill in the background.

10. The Chateau on Butterfly Trail - 6 Bdrm Retreat

Fountain City

Kathy P.

￥77,232 total

includes taxes & fees

Nov 10 - Nov 11

A log cabin with a covered porch, a door with a window, and a car parked nearby.

11. Riverfront Cabin with Private Dock

Buffalo City

Cynthia B.

￥22,539 total

includes taxes & fees

Dec 1 - Dec 2

A spacious living room with a brown sofa, a round coffee table, and a patterned rug. There is a ceiling fan, a dining area with chairs, and a staircase leading to another level.

12. Hokah Ohana House| 2BR Near La Crosse WI

Hokah

David R.

￥30,352 total

includes taxes & fees

Nov 9 - Nov 10

A wooden cabin interior with a dining table, chairs, a refrigerator, a stove, and a ladder leading to a loft.

13. Badger Cabin w/ Lofts, Fireplace & WiFi

Buffalo City

Sharon M.

￥26,652 total

includes taxes & fees

Dec 1 - Dec 2

Fun decorations throughout the apartment.
Ask us how you can rent the full floor!

14. Modern Downtown La Crosse Apartment

Historic Downtown La Crosse

Jacob P.

￥57,047 total

includes taxes & fees

Nov 9 - Nov 10

A garden with a bench and various plants.

15. The Hen House Retreat - A Comfortable Place to Roost

Highland

Lydia F.

￥29,950 total

includes taxes & fees

Nov 9 - Nov 10

A swimming pool with a water fountain, surrounded by a covered area and trees.

16. French Island w/Hot Tub, Kayak, Lake View, EV

La Crosse

Colleen C.

￥47,518 total

includes taxes & fees

Nov 10 - Nov 11

A living room with a fireplace, a sofa, a wooden coffee table, and a patterned rug.

17. Stylish 1 bedroom cottage along the Mississippi River

Stoddard

Kevin

￥24,579 total

includes taxes & fees

Nov 12 - Nov 13

A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

18. Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

Northside

Tim

￥30,438 total

includes taxes & fees

Nov 16 - Nov 17

A wooden cabin with a balcony, string lights, and outdoor furniture.

19. Tiny Treehouse Cabin | Bluff Woodlands #3

Elba

Josh S.

￥32,317 total

includes taxes & fees

Nov 11 - Nov 12

An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

20. Riverfront Twin Home

La Crosse

Jason K.

￥46,660 total

includes taxes & fees

Nov 9 - Nov 10

View all properties

Find vacation rentals that suit your style

Top Winona Hotel Reviews

A table set for a meal with various dishes, glasses of orange juice, and a vase with flowers.

Alexander Mansion Bed and Breakfast

Historic Downtown Winona

10/10 Excellent

We stayed in the Alexander Suite, which was ideal for us. King size bed, Victorian charm, tidy bathroom with tub, shower and amenities. Enjoyed the Watkins lotion. The room has an adjacent sitting room perfect for coffee, tea, or relaxing. Don't forget to write something in the journal. The host, Richard, is super nice and so knowledgeable about the area. The huge breakfast consists of 5 courses. Fruit parfait, fresh baked bread that is to die for. The blueberry was our favorite. The main...

Laila and David

A modern hotel lobby with a dining area, seating arrangements, and a stone fireplace.

Fairfield Inn & Suites by Marriott Winona

Winona

10/10 Excellent

Ginger

A hotel room with a large bed, a separate bathroom with a bathtub, a desk with a chair, and a large mirror.

AmericInn by Wyndham Winona

Winona

10/10 Excellent

MARY

A cozy living room with a fireplace, a sofa, a coffee table, and a view through large windows.

Carriage House B&B

Historic Downtown Winona

10/10 Excellent

Anonymous traveler

An indoor swimming pool with a lifeguard chair, a frog sculpture, and a whirlpool capacity sign.

Holiday Inn Express & Suites Winona by IHG

Winona

10/10 Excellent

Tyler

An outdoor seating area with brick walls, green railings, and hanging flower baskets.

The Plaza Hotel & Suites Winona

Winona

10/10 Excellent

Tim

A park with picnic tables and chairs, a large tree, and a lake in the background.

Little Bluff Inn

Downtown Trempealeau

10/10 Excellent

Sue

A living room with a fireplace, a television, and a kitchen area with a refrigerator and coffee maker.

Prairie Inn and Suites Holmen/La Cross

Holmen

10/10 Excellent

Quiet and easy access to La Crosse, City of Onalaska, and the Village of Holmen. Left DC at 6 am and had my first meeting in the Village of Holmen at 11 am. By 4 pm I was hot, tired, and wore out. Came here met a cheerful and very accomudating staff. Walked in my room, AC and partial lighting was on. Room looked great. I felt like a VIP and that rarely happens when I travel. Definitely will be back -- a great price if u stay 3 nights or more. Paul

Anonymous traveler

An outdoor seating area with wicker chairs and tables, surrounded by vibrant flowers and a red umbrella.

Stone Mill Hotel & Suites

Lanesboro

10/10 Excellent

Shari

A restaurant setting with round tables, chairs, and empty wine glasses.

Best Western Plus LaCrescent / LaCrosse

La Crescent

10/10 Excellent

Courtney

A poolside area with lounge chairs, a 'NO DIVING' sign, and a pool.

Hampton Inn & Suites La Crosse Downtown

Historic Downtown La Crosse

10/10 Excellent

Sara

A hotel room with two beds, a nightstand, and two wall-mounted lamps.

The Sawmill Inn

Houston

10/10 Excellent

Kimberly

Find out more about Winona

Search for holiday rentals in Winona on Expedia! You can easily find your home rentals, villas, holiday apartments in Winona using one of the methods below:

View our selection of featured holiday rentals in Winona
Use the map to find apartments and other holiday homes in the Winona neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Winona while they last

Look no further and take a look at our great range of rental properties in Winona!

Frequently Asked Questions

Can I find vacation rentals in Winona?

Yes, there are vacation rentals in Winona near Valencia Arts Center, or you can choose a secluded option if you want 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 vacation rentals that Winona has to offer?

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion: This vacation home rental outside of Winona offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Winona?

Expedia has 13 vacation rentals for your stay in Winona.

What can I see and do in Winona?

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

What are vacation rentals like in Winona?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Winona. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.

Winona Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winona vacation rentals

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

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

3. Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN

4. Parkside Pet Friendly Bungalow

5. Tamarack Point Homestead

6. Vintage Lustron Home Piece of History

7. Tiny Treehouse Cabin | Bluff Woodlands #2

8. Tiny Treehouse Cabin | Bluff Woodlands #1

9. Cozy River Cabin w/ Loft & Screened Porch

10. The Chateau on Butterfly Trail - 6 Bdrm Retreat

11. Riverfront Cabin with Private Dock

12. Hokah Ohana House| 2BR Near La Crosse WI

13. Badger Cabin w/ Lofts, Fireplace & WiFi

14. Modern Downtown La Crosse Apartment

15. The Hen House Retreat - A Comfortable Place to Roost

16. French Island w/Hot Tub, Kayak, Lake View, EV

17. Stylish 1 bedroom cottage along the Mississippi River

18. Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

19. Tiny Treehouse Cabin | Bluff Woodlands #3

20. Riverfront Twin Home

Find vacation rentals that suit your style

Top Winona Hotel Reviews

Alexander Mansion Bed and Breakfast

10/10 Excellent

Find out more about Winona

Frequently Asked Questions

Can I find vacation rentals in Winona?

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

How many vacation rentals are there in Winona?

What can I see and do in Winona?

What are vacation rentals like in Winona?