Vacation rentals in Winslow, IL

40 available vacation rental offers

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Best vacation rentals and Airbnb offers in Winslow, IL

Cottage In The Valley On 50 Acres. - Winslow, IL

Cottage In The Valley On 50 Acres.

Cottage, Winslow

Cottage In The Valley On 50 Acres. is a cottage in Winslow, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cottage In The Valley On 50 Acres.

Cottage In The Valley On 50 Acres. is a cottage in Winslow, 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 $717.

From$102/night
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78 Acres, On the Prairie, with a Small Trout Stream in the Driftless. - Winslow, IL

78 Acres, On the Prairie, with a Small Trout Stream in the Driftless.

Country House, Winslow

78 Acres, On the Prairie, with a Small Trout Stream in the Driftless. is a country house in Winslow, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About 78 Acres, On the Prairie, with a Small Trout Stream in the Driftless.

78 Acres, On the Prairie, with a Small Trout Stream in the Driftless. is a country house in Winslow, 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 $876.

From$125/night
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Cozy Downtown Apartment - Winslow, IL

Cozy Downtown Apartment

Apartment, Winslow

Cozy Downtown Apartment is a apartment in Winslow. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Cozy Downtown Apartment

Cozy Downtown Apartment is a apartment in Winslow. 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $933.

From$133/night
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The Minor House - A Cozy Stay in Shullsburg - Winslow, IL

The Minor House - A Cozy Stay in Shullsburg

Cottage, Winslow

The Minor House - A Cozy Stay in Shullsburg is a cottage in Winslow. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About The Minor House - A Cozy Stay in Shullsburg

The Minor House - A Cozy Stay in Shullsburg is a cottage in Winslow. 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $967.

From$138/night
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Vacation rentals with a pool in Winslow, IL

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

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake - Winslow, IL

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

Cabin, Winslow

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake is a cabin in Winslow, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Amazing Log Cabin with Beautiful Views at Apple Canyon Lake

Amazing Log Cabin with Beautiful Views at Apple Canyon Lake is a cabin in Winslow, 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 $1,897.

From$271/night
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Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location - Winslow, IL

Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location

Cabin, Winslow

Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location is a cabin in Winslow, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location

Stunning Log Cabin with amazing views at Apple Canyon Lake, Perfect Location is a cabin in Winslow, with 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,897.

From$271/night
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Beautiful Apple Canyon Lake Log Cabin in the Woods - Winslow, IL

Beautiful Apple Canyon Lake Log Cabin in the Woods

Cabin, Winslow

Beautiful Apple Canyon Lake Log Cabin in the Woods is a cabin in Winslow, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Beautiful Apple Canyon Lake Log Cabin in the Woods

Beautiful Apple Canyon Lake Log Cabin in the Woods is a cabin in Winslow, with 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,930.

From$276/night
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Vacation rentals with parking in Winslow, IL

Find vacation rentals that make arriving by car easier.

Riverfront Cabin Rental ~ 9 Mi to Yellowstone Lake - Winslow, IL

Riverfront Cabin Rental ~ 9 Mi to Yellowstone Lake

Cabin, Winslow

Riverfront Cabin Rental ~ 9 Mi to Yellowstone Lake is a cabin in Winslow, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Riverfront Cabin Rental ~ 9 Mi to Yellowstone Lake

Riverfront Cabin Rental ~ 9 Mi to Yellowstone Lake is a cabin in Winslow, 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 $1,158.

From$165/night
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Charming 4 BdRm Home - Winslow, IL

Charming 4 BdRm Home

Holiday Home, Winslow

Charming 4 BdRm Home is a holiday home in Winslow, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Charming 4 BdRm Home

Charming 4 BdRm Home is a holiday home in Winslow, 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 $1,503.

From$215/night
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3 Bedroom, Cozy Home at ACL - Winslow, IL

3 Bedroom, Cozy Home at ACL

Holiday Home, Winslow

3 Bedroom, Cozy Home at ACL is a holiday home in Winslow, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 3 Bedroom, Cozy Home at ACL

3 Bedroom, Cozy Home at ACL is a holiday home in Winslow, with parking, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,661.

From$237/night
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Pet-friendly vacation rentals in Winslow, IL

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

Pecatonica River Cabin ~ 9 Mi to Yellowstone Lake - Winslow, IL

Pecatonica River Cabin ~ 9 Mi to Yellowstone Lake

Cabin, Winslow

Pecatonica River Cabin ~ 9 Mi to Yellowstone Lake is a cabin in Winslow, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Pecatonica River Cabin ~ 9 Mi to Yellowstone Lake

Pecatonica River Cabin ~ 9 Mi to Yellowstone Lake is a cabin in Winslow, 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 $1,158.

From$165/night
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Riverfront Cabin Near Yellowstone Lake State Park - Winslow, IL

Riverfront Cabin Near Yellowstone Lake State Park

Cabin, Winslow

Riverfront Cabin Near Yellowstone Lake State Park is a cabin in Winslow, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Riverfront Cabin Near Yellowstone Lake State Park

Riverfront Cabin Near Yellowstone Lake State Park is a cabin in Winslow, 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 $1,346.

From$192/night
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Lovely 3-bedroom house with WiFi in Darlington - Winslow, IL

Lovely 3-bedroom house with WiFi in Darlington

Holiday Home, Winslow

Lovely 3-bedroom house with WiFi in Darlington is a holiday home in Winslow, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Lovely 3-bedroom house with WiFi in Darlington

Lovely 3-bedroom house with WiFi in Darlington is a holiday home in Winslow, 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, hot tub, pet friendly, pets friendly, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,477.

From$211/night
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Rustic, Romantic, Secluded, & Private - Winslow, IL

Rustic, Romantic, Secluded, & Private

Cabin, Winslow

Rustic, Romantic, Secluded, & Private is a cabin in Winslow, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Rustic, Romantic, Secluded, & Private

Rustic, Romantic, Secluded, & Private is a cabin in Winslow, 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 $1,700.

From$243/night
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Family-friendly vacation rentals in Winslow, IL

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

Riverfront Cabin Near Yellowstone Lake State Park - Winslow, IL

Riverfront Cabin Near Yellowstone Lake State Park

Cottage, Winslow

Riverfront Cabin Near Yellowstone Lake State Park is a cottage in Winslow, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Riverfront Cabin Near Yellowstone Lake State Park

Riverfront Cabin Near Yellowstone Lake State Park is a cottage in Winslow, 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 $1,471.

From$193/night
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Bring Your Pup! Historic Family Home in Darlington - Winslow, IL

Bring Your Pup! Historic Family Home in Darlington

Holiday Home, Winslow

Bring Your Pup! Historic Family Home in Darlington is a holiday home in Winslow, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Bring Your Pup! Historic Family Home in Darlington

Bring Your Pup! Historic Family Home in Darlington is a holiday home in Winslow, 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 cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,695.

From$242/night
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Family Friendly Modern Farmhouse 42 Private Acres - Winslow, IL

Family Friendly Modern Farmhouse 42 Private Acres

Holiday Home, Winslow

Family Friendly Modern Farmhouse 42 Private Acres is a holiday home in Winslow, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Family Friendly Modern Farmhouse 42 Private Acres

Family Friendly Modern Farmhouse 42 Private Acres is a holiday home in Winslow, 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 cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,331.

From$333/night
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Secluded Log Cabin w/ Private Lake & Hiking Trails - Winslow, IL

Secluded Log Cabin w/ Private Lake & Hiking Trails

Cabin, Winslow

Secluded Log Cabin w/ Private Lake & Hiking Trails is a cabin in Winslow, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Secluded Log Cabin w/ Private Lake & Hiking Trails

Secluded Log Cabin w/ Private Lake & Hiking Trails is a cabin in Winslow, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, pet friendly, pets friendly, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,612.

From$516/night
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