Winona Vacation 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
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Winona vacation rentals

Fridge, microwave, oven, stovetop

Newly renovated early 1900’s farmhouse

Newly renovated early 1900’s farmhouse
Birch Tree
10.0 out of 10, Exceptional, (24 reviews)
"Place was perfect for our stay. Beautiful property. "
United States
Drew W.
The price is ￥28,046
￥48,198 total
includes taxes & fees
May 13 - May 14
Newly renovated early 1900’s farmhouse
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 ￥49,354
￥91,944 total
includes taxes & fees
May 13 - May 14
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
Interior

Walk to Current River: Ozarks Adventure Home!

Walk to Current River: Ozarks Adventure Home!
Van Buren
10.0 out of 10, Exceptional, (1 review)
"While on a recent roadtrip we came across an undiscovered jewel in the heart of the Ozarks. Cottage on the Hill in Van Buren, MO. We found the accommodations to be private, comfortable, and very affordable. We really loved how tastefully it was furnished and the use of native woods throughout. Located at the center of the National Scenic Waterways we were able to bike down to the beautiful Current River and the legendary “Big Springs”. Our hostess, Tracy, was a wealth of knowledge with area...
United States
Jennifer
The price is ￥25,382
￥53,425 total
includes taxes & fees
May 25 - May 26
Walk to Current River: Ozarks Adventure Home!
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, (36 reviews)
"Beautiful property, I’d recommend to anyone going here to stay here."
United States
tom
The price is ￥18,802
￥23,012 total
includes taxes & fees
May 12 - May 13
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
House (1 Bedroom) | Interior

Walk to Current River: Ozarks Adventure Home!

Walk to Current River: Ozarks Adventure Home!
3.0 star property
Van Buren
The price is ￥28,359
￥52,637 total
includes taxes & fees
May 25 - May 26
Walk to Current River: Ozarks Adventure Home!
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 ￥23,972
￥36,358 total
includes taxes & fees
May 17 - May 18
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
1 bedroom, 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 ￥14,101
￥18,465 total
includes taxes & fees
May 12 - May 13
Melody King Suite. Experience peaceful relaxation in this Micro Boutique Hotel
Terrace/patio

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, (2 reviews)
"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.
The price is ￥24,677
￥39,088 total
includes taxes & fees
May 12 - May 13
Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!
Exterior detail

Hogan’s Hideout Bonnie Manor- Cozy Cottage to enjoy.

Hogan’s Hideout Bonnie Manor- Cozy Cottage to enjoy.
Eminence
6.8 out of 10, (6 reviews)
"It was close to several springs and caves as well as access to the river."
United States
Chris
The price is ￥27,419
￥40,469 total
includes taxes & fees
May 12 - May 13
Hogan’s Hideout Bonnie Manor- Cozy Cottage to enjoy.
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, (19 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 ￥17,862
￥35,210 total
includes taxes & fees
May 12 - May 13
Quiet 2 story Cabin on 32 acres near eleven point river
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, (17 reviews)
"It was beautiful and homey. We really enjoyed our stay. "
United States
Jessica
The price is ￥10,968
￥26,435 total
includes taxes & fees
May 12 - May 13
Charming 2-bedroom house with AC, WiFi in serene Van Buren
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, (2 reviews)
"Was a great little cabin"
United States
Ann C.
The price is ￥12,691
￥23,273 total
includes taxes & fees
May 12 - May 13
Cozy quiet country getaway just minutes from the Current River
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.
The price is ￥21,011
￥34,401 total
includes taxes & fees
May 12 - May 13
Cozy Corner
Interior

Newly renovated family/pet-friendly Mountain View home

Newly renovated family/pet-friendly Mountain View home
Mountain View
The price is ￥21,152
￥50,341 total
includes taxes & fees
May 18 - May 19
Newly renovated family/pet-friendly Mountain View home
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.
The price is ￥21,011
￥34,401 total
includes taxes & fees
May 12 - May 13
Easy Street Apartment
Private kitchen

Peaceful Stay Near Current River

Peaceful Stay Near Current River
Van Buren
The price is ￥30,553
￥56,604 total
includes taxes & fees
May 12 - May 13
Peaceful Stay Near Current River
4 bedrooms, 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 ￥31,728
￥38,572 total
includes taxes & fees
May 12 - May 13
H.D. Franks Guesthouse - Romantic Vintage Colonial Home in Historic Alton Mo.
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

Honeysuckle Inn - Mountain View

Honeysuckle Inn - Mountain View

8/10 Good
"Water pressure was fantastic, Beds are hard as a rock however."
Luke 1-night trip
Posted 1 day ago
Honeysuckle Inn - Mountain View

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!

Frequently asked questions

Are there vacation rentals in Winona?

Yes, we give you a choice of vacation rentals near the most popular attractions in Winona, or you can select a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Winona?

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!: Visitors give good reviews to this Winona vacation home rental, which is located on a river and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

What’s there to see and do in Winona?

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

What’s a vacation rental in Winona like?

Vacation rentals are private properties you can stay in for short or long periods in Winona. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for families.