Winona Holiday 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
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Winona holiday rentals

Interior

Charming 2-bedroom house with AC, WiFi in serene Van Buren

Charming 2-bedroom house with AC, WiFi in serene Van Buren
Van Buren
9.0 out of 10, Wonderful, (15 reviews)
"It was beautiful and homey. We really enjoyed our stay. "
United States
Jessica
The price is HK$549
HK$1,322 total
includes taxes & fees
8 Apr - 9 Apr
Charming 2-bedroom house with AC, WiFi in serene Van Buren
Outdoor dining

Quiet 2 story Cabin on 32 acres near eleven point river

Quiet 2 story Cabin on 32 acres near eleven point river
Alton
10.0 out of 10, Exceptional, (18 reviews)
"Host was very welcoming. We are an outdoors centric family and this was better than camping…very secluded and peaceful location. "
United States
Troy S.
The price is HK$893
HK$1,753 total
includes taxes & fees
6 Apr - 7 Apr
Quiet 2 story Cabin on 32 acres near eleven point river
Fridge, microwave, oven, stovetop

Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
Piedmont
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful property, I’d recommend to anyone going here to stay here."
United States
tom
The price is HK$941
HK$1,151 total
includes taxes & fees
4 Apr - 5 Apr
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
Interior

Walk to Current River: Ozarks Adventure Home!

Walk to Current River: Ozarks Adventure Home!
3.0 star property
Van Buren
The price is HK$956
HK$2,132 total
includes taxes & fees
6 Apr - 7 Apr
Walk to Current River: Ozarks Adventure Home!
Property grounds

#ContemplationCabin on the Jacks Fork River!

#ContemplationCabin on the Jacks Fork River!
Summersville
10.0 out of 10, Exceptional, (76 reviews)
"The cabin was beautiful and perfectly maintained. Our weekend stay was relaxing and memorable — everything was clean, comfortable, and thoughtfully managed. We’re already looking forward to returning in every season!"
United States
Kathia L.
The price is HK$1,959
HK$2,813 total
includes taxes & fees
9 Apr - 10 Apr
#ContemplationCabin on the Jacks Fork River!
Fridge, microwave, oven, stovetop

Newly renovated early 1900’s farmhouse

Newly renovated early 1900’s farmhouse
Birch Tree
10.0 out of 10, Exceptional, (23 reviews)
"Place was perfect for our stay. Beautiful property. "
United States
Drew W.
The price is HK$1,325
HK$2,334 total
includes taxes & fees
8 Apr - 9 Apr
Newly renovated early 1900’s farmhouse
Microwave, stovetop

Cozy quiet country getaway just minutes from the Current River

Cozy quiet country getaway just minutes from the Current River
Van Buren
10.0 out of 10, Exceptional, (1 review)
"Was a great little cabin"
United States
Ann C.
The price is HK$635
HK$1,164 total
includes taxes & fees
5 Apr - 6 Apr
Cozy quiet country getaway just minutes from the Current River
Terrace/patio

Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12

Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
Van Buren
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful stay. Good location. Very enjoyable experience."
United States
Thomas H.
The price is HK$2,469
HK$4,599 total
includes taxes & fees
8 Apr - 9 Apr
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
Interior

Hilltop House #1 with AMAZING views

Hilltop House #1 with AMAZING views
Van Buren
10.0 out of 10, Exceptional, (1 review)
"Absolutely perfect in every way, beautiful view! Host were very kind and helpful!!"
United States
Loretta B.
The price is HK$1,959
HK$2,835 total
includes taxes & fees
13 Apr - 14 Apr
Hilltop House #1 with AMAZING views
Iron/ironing board, WiFi, bed sheets

Melody King Suite. Experience peaceful relaxation in this Micro Boutique Hotel

Melody King Suite. Experience peaceful relaxation in this Micro Boutique Hotel
Alton
10.0 out of 10, Exceptional, (1 review)
"Thoroughly enjoyed our stay! Room was clean, welcoming and relaxing. Hosts were pleasant, accommodating and kind. Would highly recommend. We will definitely be back! "
United States
Paula W.
The price is HK$705
HK$924 total
includes taxes & fees
4 Apr - 5 Apr
Melody King Suite. Experience peaceful relaxation in this Micro Boutique Hotel
Smart TV, DVD player, books

Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!

Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!
Van Buren
10.0 out of 10, Exceptional, (1 review)
"Lots of room, recently remodeled and up to date. Fully stocked with just about everything you need. Host quick with response. Close to the current river, big springs national park and downtown businesses "
United States
Angela W.
Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!
Interior

Walk to Current River: Ozarks Adventure Home!

Walk to Current River: Ozarks Adventure Home!
Van Buren
The price is HK$862
HK$2,145 total
includes taxes & fees
12 Apr - 13 Apr
Walk to Current River: Ozarks Adventure Home!
Interior

Newly renovated family/pet-friendly Mountain View home

Newly renovated family/pet-friendly Mountain View home
Mountain View
The price is HK$1,058
HK$2,542 total
includes taxes & fees
9 Apr - 10 Apr
Newly renovated family/pet-friendly Mountain View home
WiFi

Cozy Corner

Cozy Corner
Van Buren
10.0 out of 10, Exceptional, (3 reviews)
"The cutest place to stay after a long day on the river! Natalie was great, and the place was very clean and comfortable."
United States
Krista M.
Cozy Corner
Exterior

Easy Street Apartment

Easy Street Apartment
Van Buren
10.0 out of 10, Exceptional, (2 reviews)
"The property was clean and comfortable. It had everything we needed for a weekend stay innVan Buren."
United States
Tara W.
Easy Street Apartment
Iron/ironing board, WiFi, bed sheets

H.D. Franks Guesthouse - Romantic Vintage Colonial Home in Historic Alton Mo.

H.D. Franks Guesthouse - Romantic Vintage Colonial Home in Historic Alton Mo.
Alton
The price is HK$2,293
HK$2,791 total
includes taxes & fees
11 Apr - 12 Apr
H.D. Franks Guesthouse - Romantic Vintage Colonial Home in Historic Alton Mo.
Interior

Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride

Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
Eminence
9.4 out of 10, Exceptional, (18 reviews)
"Very convenient location for us. The cabin is perfect for two people. "
United States
Cynthia A. S.
The price is HK$1,332
HK$1,936 total
includes taxes & fees
3 May - 4 May
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
Exterior detail

Hilltop House #2

Hilltop House #2
Van Buren
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful property. Would stay again."
United States
Sharon P.
The price is HK$1,256
HK$1,954 total
includes taxes & fees
13 Apr - 14 Apr
Hilltop House #2
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winona Hotel Reviews

Deadwood Acres cabin #2

Deadwood Acres cabin #2

8/10 Good
"Clean room Host Pet-friendly Air conditioning"
Linda W. 2-night trip
Posted 3 days ago
Deadwood Acres cabin #2

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!

Explore a world of travel with Expedia

Frequently asked questions

Are there 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.

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

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!: This highly rated holiday home rental in Winona is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

What’s there to see and do in Winona?

Mark Twain National Forest and Current River are a couple of lovely local spots to get outside and enjoy nature. While here, Ozark National Scenic Riverways and Rocky Falls are other places worth a visit.

What’s a holiday rental in Winona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winona. Holiday rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip or a small group gathering.