Discover a selection of 58 vacation rentals in Winona, MN that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and swimming pools. Prices start at $52 per night, and houses and cabins are popular options for a stay in Winona. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Winona
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Destination guide

Take in the natural beauty of Winona

The area's museums and churches are just a few of the reasons to vacation in Winona. Well known for its bird watching, wildlife and gardens, this scenic city won't disappoint. A vacation rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Things to do

Sightseeing in and around Winona

Are you hoping to find attractions to visit in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Winona a fun place to get away. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Elmaro Vineyard (8 mi / 12.8 km)
  • Cedar Valley Golf Course (8.9 mi / 14.3 km)
  • Trempealeau Moutain Golf Club (11.4 mi / 18.3 km)
  • Shenanigans Entertainment Center & Sports Bar (24.5 mi / 39.5 km)
  • Riverside Amusement Park (25.1 mi / 40.4 km)
  • UnWine'd (26.4 mi / 42.5 km)
Natural features

Exploring the natural landscape of Winona

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Winona. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Trempealeau Mountain (8.8 mi / 14.2 km)
  • Perrot State Park (9.9 mi / 15.9 km)
  • Great River Bluffs State Park (15.3 mi / 24.6 km)
  • Riverside Park (26.3 mi / 42.3 km)
  • Root River (27.9 mi / 44.9 km)
  • Grandad Bluff Park (28.4 mi / 45.7 km)
How to get there

Transportation options to and around Winona

The nearest airport is in Rochester, MN (RST-Rochester Intl.), located 42.2 mi (67.8 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into La Crosse, WI (LSE-La Crosse Municipal), which is 23.6 mi (37.9 km) away.

If you prefer train travel, the main station serving the city is Winona Station.

What are the top vacation rentals in or near Winona?

The heart wants what the heart wants, and right now it's longing for a vacation. Now's the time to pack your suitcase and head for one of these top vacation rentals in or near Winona:

  • Around 4 miles from the center of Winona, you'll love staying at "Cottage By Lake Winona". It has 3 bedrooms and a range of conveniences like a dining table and a microwave oven.
  • Another top choice is "Family Friendly In The Peaceful Heart Of Town", which is around 4 miles from Winona. Offering 3 bedrooms, an electric kettle and a garden, it has everything you need to keep you content and comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Winona vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Winona?

If you've been busier than an ant at a picnic lately, you deserve a break for a few blissful days. Leave work early on Friday and make your way to one of these weekend getaways in or near Winona:

  • "Renovated Mid - Century Modern House" is around 6 miles northwest of Winona and an ideal place to recharge your batteries. You'll like the convenient amenities here, including games and a stovetop.
  • Otherwise, make memories with your gang at "Cabin - Renovated Winona Barn With 2 Decks On 80", which is around 7 miles to the southeast of Winona. Take advantage of a kitchen, internet services and more here.

Can I find studio apartments for rent in and around Winona?

Studio apartments are a simple yet stylish option, perfectly suited for couples or solo adventurers. Spend your days exploring your new surroundings and your nights kicking back in your comfy hideaway. These vacation rentals in or near Winona are sure to please:

  • One of our favorite properties is "1 Bedroom Cabin In The Heart Of The White Water River Valley". Book a few nights or more at this popular abode and you'll have access to a garden and a washing machine.
  • Alternatively, use "Original Train Depot, Stay In This Unique Tiny House To Launch Your Activities" as a base to explore the sights around you. This comfy home away from home offers WiFi, off-street parking options and more.

Can I find short term rentals in or near Winona?

Whether you're chasing a cozy cabin or a house with enough space for the family, you'll find the ideal place on Vrbo. Treat yourself to a mini break at one of these top picks in or near Winona:

  • For a memorable vacation, it's tough to beat "Private Farmhouse - Enjoy 36 Acres To Relax". It's close to the center of Winona, along with plenty of things to see and do.
  • "Lower Level Amelia’s Place" is also ideally located. Settle in here and discover why many guests rate this property highly.

What are the best romantic weekend getaways in or near Winona?

Forget chocolates and roses. Sometimes all you need is to get away for a weekend, just you and your sweetie. At Vrbo, we've got romantic getaways in and around Winona that would make even old Cupid green with envy. Here are some we think you'll fall in love with:

  • Slip away on Friday afternoon for a couple of passion-filled evenings at "Cottage By Lake Winona". Located roughly 4 miles from Winona, it comes with lots of nice touches, including a fireplace and a dining table.
  • Alternatively, spend your mini break canoodling and uncorking Champagne at "Family Friendly In The Peaceful Heart Of Town", around 4 miles from Winona. A fireplace and a firepit will help set the mood for romance.

What are the best houses for rent with a pool in or near Winona?

Nothing screams fun like a pool. Pull out your inflatable flamingo and check out these houses in or near Winona that feature this added perk:

  • Treat your loved ones to an unforgettable break at "Renovated Mid - Century Modern House". There's plenty to love about this escape besides its pool, such as outdoor furniture and childrens activities.
  • Otherwise, spend your break at "Rural Winona Co. Guest House Getaway: Relax And Enjoy The Simple Things In Life". Along with a refreshing pool, you'll also have use of childrens activities and a microwave oven.

Don't know what to pack for your Winona escape? This impressive destination has a humid continental climate. In the summer months, expect average temperatures ranging from 55 ºF to 75 ºF. Browse our range of Winona vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more inspiration on where to stay.

What are the best large family vacation rentals in or near Winona?

Nanny and Pop-Pop, Great-Uncle Andre ... You can add them to your invitation list when you escape to a large family vacation rental in or near Winona. Get everyone you adore together at one of these spacious retreats:

  • Make your rendezvous one you won't forget at "Renovated Mid - Century Modern House". This pad has 5 bedrooms, caters to 20 guests and comes with many handy amenities, including a TV and nearby birdwatching activities. It's around 6 miles northwest of Winona.
  • Another excellent option is "Private Farmhouse - Enjoy 36 Acres To Relax". It's around 9 miles southeast of Winona, has 3 bedrooms and can accommodate up to 10 guests. Useful amenities here include coffee and tea making facilities and books.

When it's time to head out and explore, there are lots of family-friendly attractions nearby to tick off your to-do list. Lake Lodge Recreation Center is a good place to kick things off.

Can I find family cabin rentals in or near Winona?

Vacation with your kiddos in a family cabin rental in or near Winona and build some incredible new memories together. Here are a couple of favorites:

  • "Cabin - Renovated Winona Barn With 2 Decks On 80" - Enjoy fun and laughs with your gang at this escape, which is around 7 miles southeast of the center of Winona. A TV and on-site watersports are some of its family-friendly amenities.
  • "Creekside Cabin Getaway" - Another superb option, this rental comes with coffee and tea making facilities, a living room and more. You'll find it around 2 miles to the north of Winona.

For more options, use the search bar at the top of the page and adjust the filters to find the Winona vacation rental that's perfect for your needs.