Vacation rentals in Winterset, IA

82 available vacation rental offers

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Best vacation rentals and Airbnb offers in Winterset, IA

Adorable 1 bedroom duplex in quiet neighborhood. - Winterset, IA

Adorable 1 bedroom duplex in quiet neighborhood.

Holiday Home, Winterset

Adorable 1 bedroom duplex in quiet neighborhood. is a holiday home in Winterset, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Adorable 1 bedroom duplex in quiet neighborhood.

Adorable 1 bedroom duplex in quiet neighborhood. is a holiday home in Winterset, with pet-friendly space, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $613.

From$88/night
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Cheerful two bedroom duplex - Winterset, IA

Cheerful two bedroom duplex

Holiday Home, Winterset

Cheerful two bedroom duplex is a holiday home in Winterset, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cheerful two bedroom duplex

Cheerful two bedroom duplex is a holiday home in Winterset, 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 $639.

From$91/night
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Sleepover | Picturesque 1BD/1BA - Des Moines - Winterset, IA

Sleepover | Picturesque 1BD/1BA - Des Moines

Apartment, Winterset

Sleepover · Picturesque 1BD/1BA - Des Moines is a apartment in Winterset, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Sleepover | Picturesque 1BD/1BA - Des Moines

Sleepover · Picturesque 1BD/1BA - Des Moines is a apartment in Winterset, 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 $666.

From$95/night
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1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU - Winterset, IA

1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

Holiday Home, Winterset

1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU is a holiday home in Winterset, with parking and room for a group. This stay gives travelers a comfortable base…

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About 1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU

1-bedroom, 3 Gig-Fiber WiFi, timbered/view setting in WDM near RecPlex/DMU is a holiday home in Winterset, 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, parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $812.

From$116/night
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Vacation rentals with a pool in Winterset, IA

Add a pool to the search when you want an easy place to cool off between outings.

Free Breakfast, Indoor Pool, Hot Tub | King Studio - Winterset, IA

Free Breakfast, Indoor Pool, Hot Tub | King Studio

Apartment, Winterset

Free Breakfast, Indoor Pool, Hot Tub · King Studio is a apartment in Winterset, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Free Breakfast, Indoor Pool, Hot Tub | King Studio

Free Breakfast, Indoor Pool, Hot Tub · King Studio is a apartment in Winterset, with pool access 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,072.

From$153/night
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King Studio Amenities Comfort and Convenience - Winterset, IA

King Studio Amenities Comfort and Convenience

Apartment, Winterset

King Studio Amenities Comfort and Convenience is a apartment in Winterset, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About King Studio Amenities Comfort and Convenience

King Studio Amenities Comfort and Convenience is a apartment in Winterset, with pet-friendly space and pool 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, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,097.

From$157/night
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1-Bedroom | Top Location | Pool, Hot Tub Access - Winterset, IA

1-Bedroom | Top Location | Pool, Hot Tub Access

Condo, Winterset

1-Bedroom · Top Location · Pool, Hot Tub Access is a condo in Winterset, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 1-Bedroom | Top Location | Pool, Hot Tub Access

1-Bedroom · Top Location · Pool, Hot Tub Access is a condo in Winterset, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,224.

From$175/night
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Coastal Cozy Private Scenic End Unit w/Private Attached Garage/Pool/Gym - Winterset, IA

Coastal Cozy Private Scenic End Unit w/Private Attached Garage/Pool/Gym

Apartment, Winterset

Coastal Cozy Private Scenic End Unit w/Private Attached Garage/Pool/Gym is a apartment in Winterset, with pool access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Coastal Cozy Private Scenic End Unit w/Private Attached Garage/Pool/Gym

Coastal Cozy Private Scenic End Unit w/Private Attached Garage/Pool/Gym is a apartment in Winterset, with pool access, 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, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,337.

From$191/night
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Vacation rentals with parking in Winterset, IA

Find vacation rentals that make arriving by car easier.

Sleepover | Alluring 1BD/1BA - Des Moines - Winterset, IA

Sleepover | Alluring 1BD/1BA - Des Moines

Apartment, Winterset

Sleepover · Alluring 1BD/1BA - Des Moines is a apartment in Winterset, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Sleepover | Alluring 1BD/1BA - Des Moines

Sleepover · Alluring 1BD/1BA - Des Moines is a apartment in Winterset, 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 $676.

From$97/night
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Sleepover | Dashing 1BD/1BA - Des Moines - Winterset, IA

Sleepover | Dashing 1BD/1BA - Des Moines

Apartment, Winterset

Sleepover · Dashing 1BD/1BA - Des Moines is a apartment in Winterset, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Sleepover | Dashing 1BD/1BA - Des Moines

Sleepover · Dashing 1BD/1BA - Des Moines is a apartment in Winterset, 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 $676.

From$97/night
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Sleepover | Lovely 1BD/BA + High Ceilings - DSM - Winterset, IA

Sleepover | Lovely 1BD/BA + High Ceilings - DSM

Apartment, Winterset

Sleepover · Lovely 1BD/BA + High Ceilings - DSM is a apartment in Winterset, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Sleepover | Lovely 1BD/BA + High Ceilings - DSM

Sleepover · Lovely 1BD/BA + High Ceilings - DSM is a apartment in Winterset, 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 $676.

From$97/night
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Sleepover | Marvelous 1BD/1BA - Des Moines - Winterset, IA

Sleepover | Marvelous 1BD/1BA - Des Moines

Apartment, Winterset

Sleepover · Marvelous 1BD/1BA - Des Moines is a apartment in Winterset, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Sleepover | Marvelous 1BD/1BA - Des Moines

Sleepover · Marvelous 1BD/1BA - Des Moines is a apartment in Winterset, 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 $676.

From$97/night
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Pet-friendly vacation rentals in Winterset, IA

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

Wooded Views | King Bed | No Stairs - Winterset, IA

Wooded Views | King Bed | No Stairs

Apartment, Winterset

Wooded Views · King Bed · No Stairs is a apartment in Winterset, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Wooded Views | King Bed | No Stairs

Wooded Views · King Bed · No Stairs is a apartment in Winterset, with pet-friendly space, pool access, 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, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,010.

From$144/night
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Top Floor, Modern Suite with Balcony Pool Views - Winterset, IA

Top Floor, Modern Suite with Balcony Pool Views

Apartment, Winterset

Top Floor, Modern Suite with Balcony Pool Views is a apartment in Winterset, with pet-friendly space, pool access, and outdoor space. This stay gives travelers a comfortable base for…

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About Top Floor, Modern Suite with Balcony Pool Views

Top Floor, Modern Suite with Balcony Pool Views is a apartment in Winterset, with pet-friendly space, pool access, and outdoor space. 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, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,059.

From$151/night
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Brilliant Penthouse Loft Tall Ceilings & Elevator Walk to Entertainment! - Winterset, IA

Brilliant Penthouse Loft Tall Ceilings & Elevator Walk to Entertainment!

Apartment, Winterset

Brilliant Penthouse Loft Tall Ceilings & Elevator Walk to Entertainment! is a apartment in Winterset, with pet-friendly space and kitchen access. This stay gives travelers a comfortable…

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About Brilliant Penthouse Loft Tall Ceilings & Elevator Walk to Entertainment!

Brilliant Penthouse Loft Tall Ceilings & Elevator Walk to Entertainment! is a apartment in Winterset, 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 $1,088.

From$155/night
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Family-friendly vacation rentals in Winterset, IA

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

Spacious and bright 3-bedroom duplex unit with private entrance, full kitchen, washer/dryer, and off-street parking. Perfect for families, couples, or business travelers near Drake University. - Winterset, IA

Spacious and bright 3-bedroom duplex unit with private entrance, full kitchen, washer/dryer, and off-street parking. Perfect for families, couples, or business travelers near Drake University.

Apartment, Winterset

Spacious and bright 3-bedroom duplex unit with private entrance, full kitchen, washer/dryer, and off-street parking. Perfect for families, couples, or business travelers near Drake…

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About Spacious and bright 3-bedroom duplex unit with private entrance, full kitchen, washer/dryer, and off-street parking. Perfect for families, couples, or business travelers near Drake University.

Spacious and bright 3-bedroom duplex unit with private entrance, full kitchen, washer/dryer, and off-street parking. Perfect for families, couples, or business travelers near Drake University. is a apartment in Winterset, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,188.

From$170/night
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Sleeps 12…. 5 beds and a sofa sleeper. 20 min from West Des Moines.. - Winterset, IA

Sleeps 12…. 5 beds and a sofa sleeper. 20 min from West Des Moines..

Holiday Home, Winterset

Sleeps 12…. 5 beds and a sofa sleeper. 20 min from West Des Moines.. is a holiday home in Winterset, with kitchen access and room for a group. This stay gives travelers a comfortable base…

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About Sleeps 12…. 5 beds and a sofa sleeper. 20 min from West Des Moines..

Sleeps 12…. 5 beds and a sofa sleeper. 20 min from West Des Moines.. is a holiday home in Winterset, 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,396.

From$199/night
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The Silverbirch Escape Modern Comfort Meets Midwest Luxury - Winterset, IA

The Silverbirch Escape Modern Comfort Meets Midwest Luxury

Holiday Home, Winterset

The Silverbirch Escape Modern Comfort Meets Midwest Luxury is a holiday home in Winterset, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About The Silverbirch Escape Modern Comfort Meets Midwest Luxury

The Silverbirch Escape Modern Comfort Meets Midwest Luxury is a holiday home in Winterset, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,511.

From$216/night
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