Vacation rentals in Winona, MO

45 available vacation rental offers

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Best vacation rentals and Airbnb offers in Winona, MO

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

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

Holiday Home, Winona

Charming 2-bedroom house with AC, WiFi in serene Van Buren is a holiday home in Winona, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring…

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

Charming 2-bedroom house with AC, WiFi in serene Van Buren is a holiday home in Winona, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $773.

From$110/night
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Collier Cabin in Pine Hollow ~ Eminence, MO - Winona, MO

Collier Cabin in Pine Hollow ~ Eminence, MO

Cabin, Winona

Collier Cabin in Pine Hollow ~ Eminence, MO is a cabin in Winona, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Collier Cabin in Pine Hollow ~ Eminence, MO

Collier Cabin in Pine Hollow ~ Eminence, MO is a cabin in Winona, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $939.

From$134/night
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Cute and comfy bedroom with 1 queen bed/private bath - Winona, MO

Cute and comfy bedroom with 1 queen bed/private bath

Country House, Winona

Cute and comfy bedroom with 1 queen bed/private bath is a country house in Winona, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Cute and comfy bedroom with 1 queen bed/private bath

Cute and comfy bedroom with 1 queen bed/private bath is a country house in Winona, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, gym, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $973.

From$139/night
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The Woods and Willow Room. 1 queen bed ..cot can be added and private bathroom - Winona, MO

The Woods and Willow Room. 1 queen bed ..cot can be added and private bathroom

Country House, Winona

The Woods and Willow Room. 1 queen bed ..cot can be added and private bathroom is a country house in Winona, with parking. This stay gives travelers a comfortable base for exploring the…

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About The Woods and Willow Room. 1 queen bed ..cot can be added and private bathroom

The Woods and Willow Room. 1 queen bed ..cot can be added and private bathroom is a country house in Winona, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, gym, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,017.

From$145/night
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Vacation rentals with parking in Winona, MO

Find vacation rentals that make arriving by car easier.

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

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

Holiday Home, Winona

Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride is a holiday home in Winona, with parking. This stay gives travelers a comfortable base for exploring the…

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About 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 is a holiday home in Winona, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,248.

From$178/night
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Hogan's Hideout Garage Apartment, cozy, private Cabin - Winona, MO

Hogan's Hideout Garage Apartment, cozy, private Cabin

Cabin, Winona

Hogan's Hideout Garage Apartment, cozy, private Cabin is a cabin in Winona, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Hogan's Hideout Garage Apartment, cozy, private Cabin

Hogan's Hideout Garage Apartment, cozy, private Cabin is a cabin in Winona, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: parking, free parking, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,432.

From$205/night
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Newly renovated early 1900’s farmhouse - Winona, MO

Newly renovated early 1900’s farmhouse

Holiday Home, Winona

Newly renovated early 1900’s farmhouse is a holiday home in Winona, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Newly renovated early 1900’s farmhouse

Newly renovated early 1900’s farmhouse is a holiday home in Winona, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,541.

From$220/night
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The Jacks Fork Town House in Eminence - Winona, MO

The Jacks Fork Town House in Eminence

Holiday Home, Winona

The Jacks Fork Town House in Eminence is a holiday home in Winona, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Jacks Fork Town House in Eminence

The Jacks Fork Town House in Eminence is a holiday home in Winona, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,567.

From$224/night
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Pet-friendly vacation rentals in Winona, MO

Bring your pet along with stays that welcome four-legged travelers.

Current River Retreats 2 - 2 Bedroom - Sleeps 6 - Cozy Apartment - Winona, MO

Current River Retreats 2 - 2 Bedroom - Sleeps 6 - Cozy Apartment

Apartment, Winona

Current River Retreats 2 - 2 Bedroom - Sleeps 6 - Cozy Apartment is a apartment in Winona, with pet-friendly space, room for a group, and a quieter setting. This stay gives travelers a…

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About Current River Retreats 2 - 2 Bedroom - Sleeps 6 - Cozy Apartment

Current River Retreats 2 - 2 Bedroom - Sleeps 6 - Cozy Apartment is a apartment in Winona, with pet-friendly space, room for a group, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,239.

From$177/night
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Current River Retreat 4- 2 Bedroom - Sleeps 6 - Cozy Apartment - Winona, MO

Current River Retreat 4- 2 Bedroom - Sleeps 6 - Cozy Apartment

Apartment, Winona

Current River Retreat 4- 2 Bedroom - Sleeps 6 - Cozy Apartment is a apartment in Winona, with pet-friendly space, room for a group, and a quieter setting. This stay gives travelers a…

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About Current River Retreat 4- 2 Bedroom - Sleeps 6 - Cozy Apartment

Current River Retreat 4- 2 Bedroom - Sleeps 6 - Cozy Apartment is a apartment in Winona, with pet-friendly space, room for a group, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,466.

From$209/night
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River Time Cottage Get Away! 1/2 Mile from Current River! - Winona, MO

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

Holiday Home, Winona

River Time Cottage Get Away! 1/2 Mile from Current River! is a holiday home in Winona, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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

River Time Cottage Get Away! 1/2 Mile from Current River! is a holiday home in Winona, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,482.

From$212/night
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Whole house, secluded getaway near Alley Springs, Eminence , Missouri. - Winona, MO

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

Holiday Home, Winona

Whole house, secluded getaway near Alley Springs, Eminence , Missouri. is a holiday home in Winona, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base…

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

Whole house, secluded getaway near Alley Springs, Eminence , Missouri. is a holiday home in Winona, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,650.

From$236/night
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Vacation rentals with a kitchen in Winona, MO

Compare stays with kitchen access for longer trips and easier meals.

Melody King Suite. Experience peaceful relaxation in this Micro Boutique Hotel - Winona, MO

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

Holiday Home, Winona

Melody King Suite. Experience peaceful relaxation in this Micro Boutique Hotel is a holiday home in Winona, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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

Melody King Suite. Experience peaceful relaxation in this Micro Boutique Hotel is a holiday home in Winona, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $778.

From$111/night
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H.D. Franks Guesthouse - Romantic Vintage Colonial Home in Historic Alton Mo. - Winona, MO

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

Holiday Home, Winona

H.D. Franks Guesthouse - Romantic Vintage Colonial Home in Historic Alton Mo. is a holiday home in Winona, with parking and kitchen access. This stay gives travelers a comfortable base for…

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

H.D. Franks Guesthouse - Romantic Vintage Colonial Home in Historic Alton Mo. is a holiday home in Winona, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $819.

From$117/night
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The Loft on the River with Private Gravel bar!! - Winona, MO

The Loft on the River with Private Gravel bar!!

Holiday Home, Winona

The Loft on the River with Private Gravel bar!! is a holiday home in Winona, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About The Loft on the River with Private Gravel bar!!

The Loft on the River with Private Gravel bar!! is a holiday home in Winona, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,860.

From$266/night
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Cozy Cabin in the HEART of the Ozark National Scenic Riverway! - Winona, MO

Cozy Cabin in the HEART of the Ozark National Scenic Riverway!

Cabin, Winona

Cozy Cabin in the HEART of the Ozark National Scenic Riverway! is a cabin in Winona, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Cozy Cabin in the HEART of the Ozark National Scenic Riverway!

Cozy Cabin in the HEART of the Ozark National Scenic Riverway! is a cabin in Winona, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,915.

From$274/night
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Family-friendly vacation rentals in Winona, MO

Plan a trip with stays that give families more room to spread out.

Rustic Cabin Rental with Stunning Forest Views in the Ozarks, Missouri - Winona, MO

Rustic Cabin Rental with Stunning Forest Views in the Ozarks, Missouri

Cabin, Winona

Rustic Cabin Rental with Stunning Forest Views in the Ozarks, Missouri is a cabin in Winona, with room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Rustic Cabin Rental with Stunning Forest Views in the Ozarks, Missouri

Rustic Cabin Rental with Stunning Forest Views in the Ozarks, Missouri is a cabin in Winona, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, ac, air conditioning, heating, and family friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $932.

From$133/night
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Newly renovated family/pet-friendly Mountain View home - Winona, MO

Newly renovated family/pet-friendly Mountain View home

Holiday Home, Winona

Newly renovated family/pet-friendly Mountain View home is a holiday home in Winona, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring…

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About Newly renovated family/pet-friendly Mountain View home

Newly renovated family/pet-friendly Mountain View home is a holiday home in Winona, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,210.

From$173/night
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Hogan’s Hideout Bonnie Manor- Cozy Cottage to enjoy. - Winona, MO

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

Cottage, Winona

Hogan’s Hideout Bonnie Manor- Cozy Cottage to enjoy. is a cottage in Winona, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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

Hogan’s Hideout Bonnie Manor- Cozy Cottage to enjoy. is a cottage in Winona, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, ac, air conditioning, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,420.

From$203/night
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Chasen Summer! 1/2 Mile from Current River! - Winona, MO

Chasen Summer! 1/2 Mile from Current River!

Cottage, Winona

Chasen Summer! 1/2 Mile from Current River! is a cottage in Winona, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Chasen Summer! 1/2 Mile from Current River!

Chasen Summer! 1/2 Mile from Current River! is a cottage in Winona, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,482.

From$212/night
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