Vacation rentals in Sleepy Hollow, IL

30 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Sleepy Hollow, IL

Dana Guest House - Sleepy Hollow, IL

Dana Guest House

B & B, Sleepy Hollow

Dana Guest House is a b & b in Sleepy Hollow, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Dana Guest House

Dana Guest House is a b & b in Sleepy Hollow, 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 $674.

From$84/night
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Dana Guest House - Sleepy Hollow, IL

Dana Guest House

Guest House, Sleepy Hollow

Dana Guest House is a guest house in Sleepy Hollow, 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 Dana Guest House

Dana Guest House is a guest house in Sleepy Hollow, 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 paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $674.

From$84/night
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Guest House Rasha - Sleepy Hollow, IL

Guest House Rasha

B & B, Sleepy Hollow

Guest House Rasha is a b & b in Sleepy Hollow, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Guest House Rasha

Guest House Rasha is a b & b in Sleepy Hollow, 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 wifi, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,152.

From$143/night
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KING bed | Crystal Lake | McHenry | Cary | COZY - Sleepy Hollow, IL

KING bed | Crystal Lake | McHenry | Cary | COZY

Holiday Home, Sleepy Hollow

KING bed · Crystal Lake · McHenry · Cary · COZY is a holiday home in Sleepy Hollow, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About KING bed | Crystal Lake | McHenry | Cary | COZY

KING bed · Crystal Lake · McHenry · Cary · COZY is a holiday home in Sleepy Hollow, 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,334.

From$151/night
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Best Sleepy Hollow, IL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

King bed Crystal Lake Mchenry Cary Cozy - Sleepy Hollow, IL

King bed Crystal Lake Mchenry Cary Cozy

Holiday Home, Sleepy Hollow

King bed Crystal Lake Mchenry Cary Cozy is a holiday home in Sleepy Hollow, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy is a holiday home in Sleepy Hollow, with easy beach access and 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, free wifi, beachfront, beach front, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,743.

From$212/night
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Cozy Cabin In Roselle - Sleepy Hollow, IL

Cozy Cabin In Roselle

Holiday Home, Sleepy Hollow

Cozy Cabin In Roselle is a holiday home in Sleepy Hollow, 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 Cozy Cabin In Roselle

Cozy Cabin In Roselle is a holiday home in Sleepy Hollow, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,956.

From$222/night
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Charming 3-bedroom house in Roselle with Game room & fitness room - Sleepy Hollow, IL

Charming 3-bedroom house in Roselle with Game room & fitness room

Holiday Home, Sleepy Hollow

Charming 3-bedroom house in Roselle with Game room & fitness room is a holiday home in Sleepy Hollow, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Charming 3-bedroom house in Roselle with Game room & fitness room

Charming 3-bedroom house in Roselle with Game room & fitness room is a holiday home in Sleepy Hollow, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,283.

From$375/night
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Stylish 3BR Near Woodfield Mall and Parks - Sleepy Hollow, IL

Stylish 3BR Near Woodfield Mall and Parks

Holiday Home, Sleepy Hollow

Stylish 3BR Near Woodfield Mall and Parks is a holiday home in Sleepy Hollow, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Stylish 3BR Near Woodfield Mall and Parks

Stylish 3BR Near Woodfield Mall and Parks is a holiday home in Sleepy Hollow, 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 $3,434.

From$378/night
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Best Pet-Friendly Vacation Rentals in Sleepy Hollow, IL

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

Basement Suite, Separate-entrance in Prime Location - Sleepy Hollow, IL

Basement Suite, Separate-entrance in Prime Location

Holiday Home, Sleepy Hollow

Basement Suite, Separate-entrance in Prime Location is a holiday home in Sleepy Hollow, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Basement Suite, Separate-entrance in Prime Location

Basement Suite, Separate-entrance in Prime Location is a holiday home in Sleepy Hollow, 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: free cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,680.

From$200/night
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Game Room - Arcade & King Bed | LCP Collection - Sleepy Hollow, IL

Game Room - Arcade & King Bed | LCP Collection

Holiday Home, Sleepy Hollow

Game Room - Arcade & King Bed · LCP Collection is a holiday home in Sleepy Hollow, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Game Room - Arcade & King Bed | LCP Collection

Game Room - Arcade & King Bed · LCP Collection is a holiday home in Sleepy Hollow, 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 $2,268.

From$249/night
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3BR Oasis Near Advocate Sherman & St. Joseph with Fenced Yard and Fire Pit - Sleepy Hollow, IL

3BR Oasis Near Advocate Sherman & St. Joseph with Fenced Yard and Fire Pit

Holiday Home, Sleepy Hollow

3BR Oasis Near Advocate Sherman & St. Joseph with Fenced Yard and Fire Pit is a holiday home in Sleepy Hollow, with room for a group. This stay gives travelers a comfortable base for…

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About 3BR Oasis Near Advocate Sherman & St. Joseph with Fenced Yard and Fire Pit

3BR Oasis Near Advocate Sherman & St. Joseph with Fenced Yard and Fire Pit is a holiday home in Sleepy Hollow, 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,339.

From$251/night
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The Green House - Sleepy Hollow, IL

The Green House

Holiday Home, Sleepy Hollow

The Green House is a holiday home in Sleepy Hollow, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Green House

The Green House is a holiday home in Sleepy Hollow, 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 $3,406.

From$383/night
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Our Favorite Family-Friendly Vacation Rentals in Sleepy Hollow, IL

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

Riverfront Cottage/sauna/ kayaks/dock/firepit - Sleepy Hollow, IL

Riverfront Cottage/sauna/ kayaks/dock/firepit

Cottage, Sleepy Hollow

Riverfront Cottage/sauna/ kayaks/dock/firepit is a cottage in Sleepy Hollow, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Riverfront Cottage/sauna/ kayaks/dock/firepit

Riverfront Cottage/sauna/ kayaks/dock/firepit is a cottage in Sleepy Hollow, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,308.

From$271/night
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Game room+ New Bath! Near Chicago and O’Hare +Fenced yard - Sleepy Hollow, IL

Game room+ New Bath! Near Chicago and O’Hare +Fenced yard

Holiday Home, Sleepy Hollow

Game room+ New Bath! Near Chicago and O’Hare +Fenced yard is a holiday home in Sleepy Hollow, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Game room+ New Bath! Near Chicago and O’Hare +Fenced yard

Game room+ New Bath! Near Chicago and O’Hare +Fenced yard is a holiday home in Sleepy Hollow, 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: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,720.

From$301/night
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Cozy 3BR Home – Family-Friendly, Near Schaumburg - Sleepy Hollow, IL

Cozy 3BR Home – Family-Friendly, Near Schaumburg

Holiday Home, Sleepy Hollow

Cozy 3BR Home – Family-Friendly, Near Schaumburg is a holiday home in Sleepy Hollow, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Cozy 3BR Home – Family-Friendly, Near Schaumburg

Cozy 3BR Home – Family-Friendly, Near Schaumburg is a holiday home in Sleepy Hollow, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,355.

From$367/night
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Family Heaven Retreat, 6 Bedroom, Sleep 16 - Sleepy Hollow, IL

Family Heaven Retreat, 6 Bedroom, Sleep 16

Holiday Home, Sleepy Hollow

Family Heaven Retreat, 6 Bedroom, Sleep 16 is a holiday home in Sleepy Hollow, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Family Heaven Retreat, 6 Bedroom, Sleep 16

Family Heaven Retreat, 6 Bedroom, Sleep 16 is a holiday home in Sleepy Hollow, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,965.

From$659/night
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