Photo by Jessica Richter

Holiday Homes in Winona

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
19 Sept - 21 Sept
In two weeks
26 Sept - 28 Sept
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov

Featured Holiday Homes in Winona

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

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

2.0 star property
9.0 out of 10, Wonderful, (12)
"Lovely little house that fit our needs for a few days during a family reunion. Very quick access to a Dollar General, liquor store and gas station. And only a couple quick miles to the Landing. "
The price is NZ$270
includes taxes & fees
23 Sept - 24 Sept
Charming 2-bedroom house with AC, WiFi in serene Van Buren
2 Bedroom Home less than 2 miles to Jacks Fork River
Fridge, microwave, oven, stovetop

2 Bedroom Home less than 2 miles to Jacks Fork River

9.8 out of 10, Exceptional, (25)
"Check in was easy and the house was clean!"
2 Bedroom Home less than 2 miles to Jacks Fork River
Triple H Properties
Property grounds

Triple H Properties

8.6 out of 10, Excellent, (27)
"Lori’s place was a nice spot for a two night stay"
Triple H Properties
Guests enjoy their own one bedroom apartment in the Ozarks
Property grounds

Guests enjoy their own one bedroom apartment in the Ozarks

10.0 out of 10, Exceptional, (70)
"Relaxing cute little apt with everything you need. "
Guests enjoy their own one bedroom apartment in the Ozarks
Beautiful 3-bedrm , 3.5 ba Log/Stone in Eminence MO. Will sleep up to 16 guests.
Smart TV, fireplace, video library

Beautiful 3-bedrm , 3.5 ba Log/Stone in Eminence MO. Will sleep up to 16 guests.

9.8 out of 10, Exceptional, (7)
"Great space!"
Beautiful 3-bedrm , 3.5 ba Log/Stone in Eminence MO. Will sleep up to 16 guests.
Unbeatable convenience in amazing Eminence!
Dining

Unbeatable convenience in amazing Eminence!

10.0 out of 10, Exceptional, (17)
"Great time. Clean place. Easy access to town and river. Penty of amenities (cooking utensils, bathroom supplies, games and movies) Beds were comfortable and plenty of linens. Quiet inside from outdoor noise."
Unbeatable convenience in amazing Eminence!
The Cabin on Current River with Private Gravel Bar!!
Outdoor dining

The Cabin on Current River with Private Gravel Bar!!

8.8 out of 10, Excellent, (27)
"Beautiful area, secluded. We enjoyed staying at this property and access to the river was as expected."
The Cabin on Current River with Private Gravel Bar!!
Private scenic Ozark Mountain retreat near beautiful Current River; sleeps 1-10!
Terrace/patio

Private scenic Ozark Mountain retreat near beautiful Current River; sleeps 1-10!

10.0 out of 10, Exceptional, (21)
"Cute house, great accommodations, great location!"
Private scenic Ozark Mountain retreat near beautiful Current River; sleeps 1-10!
Unique cabins in the woods<br>Not friendly for Street Bikes.
Fridge, microwave, oven, stovetop

Unique cabins in the woods<br>Not friendly for Street Bikes.

10.0 out of 10, Exceptional, (107)
"Very nice people and place"
Unique cabins in the woods<br>Not friendly for Street Bikes.
4-bedroom RIVER FRONT home located on the beautiful Current River in Van Buren
Property grounds

4-bedroom RIVER FRONT home located on the beautiful Current River in Van Buren

10.0 out of 10, Exceptional, (2)
"The propertyb was great spacious and very accomodating "
4-bedroom RIVER FRONT home located on the beautiful Current River in Van Buren
Sunshine Shack at Clearwater Lake (sleeps 6)
Property grounds

Sunshine Shack at Clearwater Lake (sleeps 6)

8.8 out of 10, Excellent, (10)
"Loved staying a week at Sunshine Shack. The screened in deck is perfect to watch the deer at dusk."
Sunshine Shack at Clearwater Lake (sleeps 6)
The Loft on the River with Private Gravel bar!!
Property grounds

The Loft on the River with Private Gravel bar!!

8.0 out of 10, Very good, (19)
"We had a great time and other than there was no broom so hard to sweep the sand from the beach, but that was very minor. Overall it was clean and we all enjoyed it! Will come back again next year!"
The Loft on the River with Private Gravel bar!!
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
Terrace/patio

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

2.0 star property
10.0 out of 10, Exceptional, (8)
"Loved this property. New home near town and hiking trails of the Ozark National Scenic Wayerways. Conveniences near by. Homes is in excellent condition and recently constructed with all new interior furnishings. Owner is excellent to work with. Responded to needs and questions immediately. "
The price is NZ$955
includes taxes & fees
23 Sept - 24 Sept
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
RIVER FRONT HOUSE
Property grounds

RIVER FRONT HOUSE

9.6 out of 10, Exceptional, (41)
"House was in a great location for a family stay."
RIVER FRONT HOUSE
Newly renovated early 1900’s farmhouse
Fridge, microwave, oven, stovetop

Newly renovated early 1900’s farmhouse

10.0 out of 10, Exceptional, (18)
"Great little house. "
The price is NZ$490
includes taxes & fees
1 Oct - 2 Oct
Newly renovated early 1900’s farmhouse
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
Outdoor dining

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

9.4 out of 10, Exceptional, (14)
"Decent place, lots of ladybugs in the house!"
The price is NZ$370
includes taxes & fees
23 Sept - 24 Sept
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
Barn by The Creek- Barn turned bnb on a creek in Eminence, sleeps 10
Property grounds

Barn by The Creek- Barn turned bnb on a creek in Eminence, sleeps 10

10.0 out of 10, Exceptional, (5)
Barn by The Creek- Barn turned bnb on a creek in Eminence, sleeps 10
Scenic Riverways Retreat + Bunkhouse – Perfect for Families & Groups
Fridge, microwave, oven, stovetop

Scenic Riverways Retreat + Bunkhouse – Perfect for Families & Groups

10.0 out of 10, Exceptional, (2)
"The stay was great and the place has everything you need!"
Scenic Riverways Retreat + Bunkhouse – Perfect for Families & Groups
Whole house, secluded getaway near Alley Springs, Eminence , Missouri.
Exterior

Whole house, secluded getaway near Alley Springs, Eminence , Missouri.

10.0 out of 10, Exceptional, (3)
"This location was a perfect place for a large family gathering. There was adequate space for a couple of families to stay overnight! Close to Harvey’s canoe/raft rentals! The host was very helpful!"
Whole house, secluded getaway near Alley Springs, Eminence , Missouri.
River Time Cottage Get Away! 1/2 Mile from Current River!
Outdoor dining

River Time Cottage Get Away! 1/2 Mile from Current River!

9.4 out of 10, Exceptional, (31)
"We had a great time during our stay and the house was comfortable and close to everything. Will definitely stay here again!"
River Time Cottage Get Away! 1/2 Mile from Current River!
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.
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

The Cottage Room has 2 queen beds and private bathroom

The Cottage Room has 2 queen beds and private bathroom

10/10 Excellent
"We had an amazing trip! The property was clean and the host was very accommodating! Would highly recommend if you’re in the area for a float down Jack Forks River!"
Robert B. 2-night trip
Posted 1 month ago
The Cottage Room has 2 queen beds and private bathroom

Find out more about Winona

Find out more about Winona

Winona Holiday Homes information

Number of reviews
Accommodation
42 Holiday Homes
Lowest Price
NZ$270
Highest Price
NZ$955

Explore a world of travel with Expedia

Explore a world of travel with Expedia