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Top Holiday Rentals in Winona

Creekside Cabin Getaway

9.4 out of 10, Exceptional, (108)
"It was a peaceful place beautiful cabin I would definitely recommend "
Creekside Cabin Getaway

Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

10.0 out of 10, Exceptional, (13)
"Clean property, affordable price, good experience all around!"
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

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

10.0 out of 10, Exceptional, (18)
"This house was perfect for our weekend stay. It is super clean & updated. The beds and living room sofa were very comfortable. Andrea has thought of everything in supplying the extras that you might need! Will definitely stay here again!"
The price is £230
includes taxes & fees
26 Aug - 27 Aug
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

Big River Escape Parkside Bungalow

3.0 star property
The price is £141
includes taxes & fees
27 Aug - 28 Aug
Big River Escape Parkside Bungalow

This AMAZING river getaway is PERFECT for YOU! Private deck, grill & fire pit!

9.6 out of 10, Exceptional, (4)
"Unique location close to downtown Winona-perfect for our family gathering!"
This AMAZING river getaway is PERFECT for YOU! Private deck, grill & fire pit!

The Broadway Exchange

9.8 out of 10, Exceptional, (29)
"We had a great time staying here. Kitchen was perfect for meals with the family and so conveniently located—minutes from town and WSU! Beds were comfy and very cozy sheets and blankets. Will absolutely stay here again!"
The Broadway Exchange

Charming Brick Farmhouse with a Touch of Elegance. -Winona

10.0 out of 10, Exceptional, (130)
"It was very comfortable house to stay in snd share our time together. "
The price is £362
includes taxes & fees
2 Sept - 3 Sept
Charming Brick Farmhouse with a Touch of Elegance. -Winona

Big River Escape Riverside Cabins

3.0 star property
9.2 out of 10, Wonderful, (33)
"Beautiful stay"
The price is £84
includes taxes & fees
1 Sept - 2 Sept
Big River Escape Riverside Cabins

The Bungaleau 1 Bedroom House In Cute Rivertown

9.8 out of 10, Exceptional, (83)
"Great place to stay for a visit to Trempealeau and the surrounding area. "
The price is £122
includes taxes & fees
31 Aug - 1 Sept
The Bungaleau 1 Bedroom House In Cute Rivertown

Cabin on the Mississippi River

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

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."
The price is £150
includes taxes & fees
27 Aug - 28 Aug
The Hen House Retreat - A Comfortable Place to Roost

Toddy's Cabin

10.0 out of 10, Exceptional, (117)
"Loved the large screened porch and private yard! Inside the cabin was clean and comfortable. It is the only place on the last hundred yards or so of a dead end road. A short walk from the Mississippi River and a 5 minute drive or 25 minute walk to a beautiful State Park with great hiking. If you are a light sleeper the trains might be an issue but we thought it was cool to have those distant train whistles."
Toddy's Cabin

Heritage hideaway-Secluded Log Cabin

10.0 out of 10, Exceptional, (392)
"The property is beautiful and very well maintained. It has everything you could want to enjoy your stay. The views and outdoor fire pit are fabulous. I highly recommend staying here"
Heritage hideaway-Secluded Log Cabin

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

Secluded Home - Views of Mississippi River remote location 15 min from La Crosse

10.0 out of 10, Exceptional, (160)
"Truly enjoyed our time here- perfect gathering spot for family and friends. Clean, comfortable, and great location for day trips. Loved the upper level kitchen, pool, darts, game room! "
Secluded Home - Views of Mississippi River remote location 15 min from La Crosse

8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

10.0 out of 10, Exceptional, (148)
"Enjoyed our stay. House worked out great- the number of beds/bedrooms and having 2 bathrooms was wonderful. Close to the downtown- easy 30 minute walk."
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

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."
The price is £368
includes taxes & fees
26 Aug - 27 Aug
Star Hawk Springs Chateaux - Large 6 Bdrm Retreat

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!

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.

Root River Valley Cabin ~ Lanesboro, MN

10.0 out of 10, Exceptional, (322)
"Spacious log cabin in a great location."
Root River Valley Cabin ~ Lanesboro, MN
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 Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Winona?

Yes, there are holiday rentals close to the most popular sights in Winona, 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?

Fountain City Loft, hot tub, river views: This holiday home rental outside of Winona is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Winona?

Expedia has 15 holiday rentals for your stay in Winona.

What can I see and do in Winona?

Enjoy the outdoors at Sugar Loaf and Mississippi River, or simply take in cultural attractions like Minnesota Marine Art Museum and Winona County Historical Society. While here, Great River Bluffs State Park and Winona County Courthouse 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.