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Winona vacation rentals

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Top-rated vacation rentals in Winona

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Home in Pepin

4.95 out of 5 average rating, 85 reviews

Villa Serra - Lakehouse in Pepin

Villa Serra is located in beautiful Pepin, Wisconsin. This unique 3 bedroom 2 full bath home boasts panoramic views of Lake Pepin. The open floor plan features a spacious living room with adjoining kitchen and breakfast bar island. The dining area leaded to an elevated open porch and deck with expansive views. Stroll through the hillside gardens and relax on the deck overlooking the lake - a perfect setting for gathering, enjoying the gas BBQ and dining al fresco. The perfect Lake Pepin retreat!

Home in Reads Landing

4.99 out of 5 average rating, 149 reviews

Gorgeous home overlooking the Mississippi River

Gorgeous, secluded home moments away from Wabasha. Free WiFi. Enjoy Septoberfest, one of the many terrific restaurants in the area, Music Under the Bridge, or any other fun activity this little river town has to offer. The house is fully furnished, with two bedrooms, but with room to sleep more. This is a one-of-a-kind property with a view that could only best be described by simply reading our reviews. Located south of Red Wing, between Lake City and Wabasha, in Reads Landing, Minnesota.

Home in Frontenac

4.91 out of 5 average rating, 43 reviews

Charming 3 bed/3bath renovated cabin on Lake Pepin

This is the perfect quiet getaway! High end renovation with 100 ft of private beach on breath-taking Lake Pepin. Revel in this home’s private owner’s suite, sunny open floor plan, wood fireplace, expansive deck, and incredible lake views. *Per local ordinance: 6 guests max over 5yrs old, no parties/events. *No more than 3 vehicles allowed. *No more than 3 additional guests allowed *No recreational vehicles, campers, or tent camping allowed. *Quiet outdoor hours from 9pm-9am. *No fireworks

Cabin in Mindoro

4.98 out of 5 average rating, 83 reviews

Stunning Views! - Pettinger @HighPointRetreats

Perched in the solitude of nature, our ridge top cabin offers a picturesque view at one of the top elevations in all La Crosse County. Cozy up to your loved ones, relax with friends, or find inspiration in this luxury cabin in the woods. Pettinger cabin is named after Petting Summit located just east of the cabin. Pettinger sleeps four and is non-smoking. Get your front row sunset seats on the private patio and relax by the fire. Immerse yourself in the tranquility and come stay us.

Home in Lake City

5 out of 5 average rating, 19 reviews

"Amazing Views" of Lake Pepin in Lake City

Amazing Views is Lake City's "Premiere" Vacation Rental! From its perfect location, to the absolutely Amazing Views and lake cottage feel, you will love this home! Enjoy Adirondack chairs under the pergola in the summer to watch the eagles, pelicans and sailboats. Cuddle up by the red brick, gas fireplace in the living room in the winter. A perfect home for every season. Just 2 blocks away from Ohuta Beach and the Marina. Bring your friends and family to this "Amazing" home!

Cabin in Black River Falls

4.97 out of 5 average rating, 29 reviews

Riverfront-Sandy Beach-TikiBar-Dock-RecRoom-3700ft

NEW! Rustic getaway on the Black River, Jackson County, Wisconsin. Perfect for large family gatherings in all 4 seasons, this home has it all boasting numerous bedrooms and living spaces, a recreation room (pool/ping pong)/arcade/bar, fireplace(s), and indoor and outdoor views of the river. Dip your toes in the perfectly sandy beach (hard-to-find) and relax on the deck or enjoy a cocktail at the Tiki bar. This space is sure to leave you with memories that will last a lifetime.

Condo in Pepin

4.97 out of 5 average rating, 35 reviews

Boho Condo 1 block from the water

"Welcome to the Boho Condo above The Pepin Labyrinth Yoga Studio! Its prime location ensures that everything you need is within easy reach. One block from the Marina, Harbor View Cafe, and gas stations. Two blocks from The Pickle Factory restaurant. Within walking distance to E&S Fresh Market, River Time Wine and Beer, and local shops. And a short drive to Villa Bellezza Winery. The Boho Condo provides a peaceful and calming atmosphere, making it the perfect retreat."

Home in Wabasha

5 out of 5 average rating, 26 reviews

The Cottage

This unique and quaint cottage is a perfect get away for 2. Located a block from the walking path, Isaak Walton park and Parkside Marina, this quiet cottage is a central spot for many activities. Take the walking path to the beach or head downtown to the Eagle Center. This cottage boasts many different plants in its secluded gardens. Sit on the back porch and sip your morning coffee, or take a nice bubble bath in the claw foot tub. You’ll be sure to find solace here.

Rental unit in Viroqua

4.98 out of 5 average rating, 123 reviews

Two Bedroom upstairs airy modern apartment

This upper level apartment has beautiful natural light, a combined living/dining space, two well-appointed bedrooms with built-in desks, a fully furnished vintage kitchen, a full bath, and a private deck. It is available at a discounted price for longer stays. This apartment is part of three apartments in an older home but has a private indoor and outdoor access point. Two queen beds, one single bed and one sleeper sofa. Reserved parking by the entry door.

Cabin in Onalaska

4.63 out of 5 average rating, 48 reviews

Cozy Corner Cottages Cabin Rental

We hope you choose to stay at Cozy Corner Cottages! Winter season specials are here! We welcome ice fishers, snowmobilers, hunters, or anyone wanting to have time to relax this winter! The cabins are located on Lake Onalaska in Onalaska, WI and near La Crosse, WI. Cozy Corner Cottages is a small 5 cabin resort. It is a very popular destination during fishing and hunting seasons. Many families visit throughout the summer. CABINS ARE PET FRIENDLY!

Rental unit in Westby

4.91 out of 5 average rating, 101 reviews

Borgens Vacation Rentals Apt. #3

This two bedroom apartment is located in downtown Westby. Near Bike Trails, World Class Trout Fishing, Cross Country Ski Trails, Snowmobile Trails, Amish Tours, and Local Shopping. The apartment is newly renovated and fully furnished. It is located above a great cafe featuring homemade comfort food. This place is good for couples, solo adventurers, business travelers, and families (with kids). We do not allow pets.

Home in Minneiska

5 out of 5 average rating, 16 reviews

Riverview Radiance: 5BR, Scenic Views, Pets OK

Discover ‘Riverview Radiance,' a 5BR Minneiska marvel where the Mississippi meets modern luxury. Perfect for large groups, this home boasts a fully-equipped kitchen, sprawling views, and a suite of entertainment options. Revel in comfort with plush bedding and a cozy fireplace, all while soaking in nature's grandeur.

Vacation rentals for every style

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Apartments

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A space thats all yours, with room for everyone

Popular amenities for Winona vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Winona's top sights

Minnesota Marine Art Museum32 locals recommend

Garvin Heights Lookout17 locals recommend

Island City Brewing Company Co14 locals recommend

Blue Heron Coffeehouse15 locals recommend

Acoustic Cafe15 locals recommend

The Boat House Restaurant14 locals recommend

Other great vacation rentals in Winona

Farm stay in Mondovi

4.96 out of 5 average rating, 27 reviews

Vintage 2 Bedroom Farm House

Barn in Hixton

4.89 out of 5 average rating, 251 reviews

A Suite Getaway

Home in Black River Falls

4.82 out of 5 average rating, 98 reviews

Casa Bella Rosa - Private Custom Estate

Home in Lanesboro

5 out of 5 average rating, 57 reviews

Lanesboro Irish Ridge Retreat

Cabin in Black River Falls

4.98 out of 5 average rating, 56 reviews

Powerhouse Cabin

Home in Onalaska

4.93 out of 5 average rating, 14 reviews

Cozy, quiet place w/pool/hot tub

Home in La Crosse

4.95 out of 5 average rating, 19 reviews

Comfortable, Hyde Away Home

Cabin in Black River Falls

4.95 out of 5 average rating, 44 reviews

Beautiful Cabin Secluded In The Woods

Quick stats about vacation rentals in Winona

Total rentals
70 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
7K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Winona?
Yes! Work meets play with ease at over 30 vacation rentals in Winona featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winona?
Four-legged friends are welcome in Winona. Choose from more than 10 vacation rentals for guests traveling with pets.
Do apartment rentals in Winona have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Winona. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winona have wifi?
Absolutely! We offer over 20 house rentals with wifi in Winona. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winona?
Winona has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Winona have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Winona. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Winona?
Experience the best of Winona with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Winona?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with air conditioning, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

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