Vacation Rentals in Winona County

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Top Cities in Winona County

Top Vacation Rentals in Winona County

Our top choices for Winona County vacation rentals

Creekside Cabin Getaway

9.4 out of 10, Exceptional, (108)
"Everything is as promised and we enjoyed the house. Enjoyed talking with Tanya and Jasper and one of the chickens visited us on the balcony. We also enjoyed walking by the creek.It is on the list of properties we want to come back to next year. "
Creekside Cabin Getaway

Ridgetop Retreat Tiny Home, Dakota MN

2.0 star property
9.8 out of 10, Exceptional, (6)
"The Tiny House is what the name implies but there was ample space for 2 adults, 1 teenager and our dog. Everything is like new. Lots of outdoor space and a great walking trail. Would recommend and stay here again."
$128 nightly
The price is $138
Sep 1 - Sep 2
Total with taxes and fees
Ridgetop Retreat Tiny Home, Dakota MN

Treehouse Cabin in the Bluff Woodlands North

9.6 out of 10, Exceptional, (7)
"Great area a place to stay. "
$160 nightly
The price is $172
Sep 1 - Sep 2
Total with taxes and fees
Treehouse Cabin in the Bluff Woodlands North

Treehouse Cabin in the Bluff Woodlands South

10.0 out of 10, Exceptional, (10)
"My family of 4 had a wonderful stay!"
$160 nightly
The price is $172
Sep 1 - Sep 2
Total with taxes and fees
Treehouse Cabin in the Bluff Woodlands South

Treehouse Cabin in the Bluff Woodlands

9.8 out of 10, Exceptional, (15)
"Beautiful property. Cabins are comfy & warm. Awesome quilts. Really quiet & peaceful. "
$160 nightly
The price is $172
Sep 1 - Sep 2
Total with taxes and fees
Treehouse Cabin in the Bluff Woodlands

Big River Escape Riverside Cabins

3.0 star property
9.2 out of 10, Wonderful, (33)
"Beautiful stay"
$95 nightly
The price is $101
Sep 1 - Sep 2
Total with taxes and fees
Big River Escape Riverside Cabins

NEW, NEW, NEW! Wabasha downtown studio113 Pembroke Ave Unit #102

10.0 out of 10, Exceptional, (57)
"Great place, loved it."
$160 nightly
The price is $172
Sep 28 - Sep 29
Total with taxes and fees
NEW, NEW, NEW! Wabasha downtown studio113 Pembroke Ave Unit #102

The Bungaleau 1 Bedroom House In Cute Rivertown

9.8 out of 10, Exceptional, (85)
"Great place to stay for a visit to Trempealeau and the surrounding area. "
$145 nightly
The price is $160
Sep 7 - Sep 8
Total with taxes and fees
The Bungaleau 1 Bedroom House In Cute Rivertown

Waterfront Condo steps from the Mississippi River

9.8 out of 10, Exceptional, (120)
"Great location and excellent rental!"
Waterfront Condo steps from the Mississippi River

Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!

10.0 out of 10, Exceptional, (39)
"House was perfect, clean and cozy! Will definitely book again!"
Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!

Clean, fun, comfy ranch home near parks, 2.5 mi to Mayo w Pingpong and Playroom

10.0 out of 10, Exceptional, (56)
"This was the perfect place for us to stay, everything was comfortable and had just what we needed. Not far from Mayo Clinic. "
Clean, fun, comfy ranch home near parks, 2.5 mi to Mayo w Pingpong and Playroom

Fountain City Loft, hot tub, river views

10.0 out of 10, Exceptional, (25)
"We enjoyed the accommodations. Would highly recommend."
Fountain City Loft, hot tub, river views

Cabin on the Mississippi River

10.0 out of 10, Exceptional, (80)
"Great place!!"
Cabin on the Mississippi River

River Front Property

10.0 out of 10, Exceptional, (96)
"We enjoyed our stay and everything was as expected and described. Will stay again. "
River Front Property

NEW Build Home with Outdoor Oasis | Game Room | Bunkroom

10.0 out of 10, Exceptional, (4)
"We had a great stay and experience! The property offered fun and relaxation for all ages in our group. We would highly recommend staying here!"
$441 nightly
The price is $454
Sep 1 - Sep 2
Total with taxes and fees
NEW Build Home with Outdoor Oasis | Game Room | Bunkroom

Star Hawk Springs Chateaux - Large 6 Bdrm Retreat

8.2 out of 10, Very Good, (12)
"Great place to stay, worked out perfect for our family."
$469 nightly
The price is $492
Sep 3 - Sep 4
Total with taxes and fees
Star Hawk Springs Chateaux - Large 6 Bdrm Retreat

The Hen House Retreat - A Comfortable Place to Roost

9.6 out of 10, Exceptional, (84)
"We enjoyed taking it easy watching some movies and crafting together for the weekend."
$185 nightly
The price is $199
Sep 1 - Sep 2
Total with taxes and fees
The Hen House Retreat - A Comfortable Place to Roost

Victorian era Mississippi riverview retreat.

9.8 out of 10, Exceptional, (30)
"Property was clean, comfortable, and just what we were looking for."
Victorian era Mississippi riverview retreat.

Valley Cabin

9.0 out of 10, Wonderful, (6)
"Great property with plenty of outdoor activities. Had fun fishing the stream and exploring the area. Dan is a great host and I will be visiting again."
$118 nightly
The price is $127
Sep 1 - Sep 2
Total with taxes and fees
Valley Cabin

Sunrise on Skyline - Indoor Pool - Arcades - Amazing Views!

10.0 out of 10, Exceptional, (76)
"Property was just what our family in town for a wedding needed. Room for everyone and a fantastic view!"
Sunrise on Skyline - Indoor Pool - Arcades - Amazing Views!
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.
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Top Winona County Hotel Reviews

Find out more about Winona County

Find out more about Winona County

Discover your perfect Winona County vacation rental with Expedia

How many vacation rentals are available in Winona County?


Expedia has plenty of vacation rentals to choose from in and around  Winona County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Winona County?


The selection of Winona County vacation rentals we have selected for you start as low as $101 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Winona County?


Vacation rentals in Winona County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Winona County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Winona County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Winona County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Winona County?


Find vacation rentals in Winona County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Winona County.  


What amenities are available in a vacation rental in Winona County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Winona County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Winona County?   


Everytime is a great time to head to Winona County! Staying in a Winona County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Winona County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Winona County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Winona County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Winona County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.