Vacation rentals in Boystown, IL

105 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Boystown, IL

Chicago Avenue Inn - Boystown, IL

Chicago Avenue Inn

Guest House, Boystown

Chicago Avenue Inn is a guest house in Boystown, 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 Chicago Avenue Inn

Chicago Avenue Inn is a guest house in Boystown, 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 $1,063.

From$90/night
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Cozy Studio Getaway Walk to Dining and Shops + Laundry - Boystown, IL

Cozy Studio Getaway Walk to Dining and Shops + Laundry

Apartment, Boystown

Cozy Studio Getaway Walk to Dining and Shops + Laundry is a apartment in Boystown, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Studio Getaway Walk to Dining and Shops + Laundry

Cozy Studio Getaway Walk to Dining and Shops + Laundry is a apartment in Boystown, 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 washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,226.

From$175/night
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Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake - Boystown, IL

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Apartment, Boystown

Regal Stylish Loft Rooftop · 13 mins DT · 4 mins Lake is a apartment in Boystown, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop · 13 mins DT · 4 mins Lake is a apartment in Boystown, 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: pet friendly, pets friendly, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,267.

From$181/night
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Cozy unit steps from Loyola Uni with AC, WiFi, fitness room and big TV - Boystown, IL

Cozy unit steps from Loyola Uni with AC, WiFi, fitness room and big TV

Apartment, Boystown

Cozy unit steps from Loyola Uni with AC, WiFi, fitness room and big TV is a apartment in Boystown, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base…

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About Cozy unit steps from Loyola Uni with AC, WiFi, fitness room and big TV

Cozy unit steps from Loyola Uni with AC, WiFi, fitness room and big TV is a apartment in Boystown, 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 $1,278.

From$183/night
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Best Boystown, IL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT - Boystown, IL

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Apartment, Boystown

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT is a apartment in Boystown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT

Comfy Bed/Free Parking&Wifi /NearHosp/ORD/MDW/DT is a apartment in Boystown, 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 $1,269.

From$181/night
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Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!! - Boystown, IL

Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!

Apartment, Boystown

Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!! is a apartment in Boystown, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!!

Comfortable home in historic Oak Park- open For Thanksgiving and Christmas!!! is a apartment in Boystown, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,270.

From$181/night
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Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW - Boystown, IL

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Apartment, Boystown

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW is a apartment in Boystown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW

Spacious APT/Comfy Bed/Free Parking/22mins to ORD&MDW is a apartment in Boystown, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,298.

From$185/night
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2-bedroom apartment in Downtown Skokie AC,Walk to train shoppings restaurants! - Boystown, IL

2-bedroom apartment in Downtown Skokie AC,Walk to train shoppings restaurants!

Apartment, Boystown

2-bedroom apartment in Downtown Skokie AC,Walk to train shoppings restaurants! is a apartment in Boystown, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About 2-bedroom apartment in Downtown Skokie AC,Walk to train shoppings restaurants!

2-bedroom apartment in Downtown Skokie AC,Walk to train shoppings restaurants! is a apartment in Boystown, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,446.

From$207/night
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Best Pet-Friendly Vacation Rentals in Boystown, IL

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

Luxurious, Cozy Beauty 10 min from Downtown Chicago - Boystown, IL

Luxurious, Cozy Beauty 10 min from Downtown Chicago

Apartment, Boystown

Luxurious, Cozy Beauty 10 min from Downtown Chicago is a apartment in Boystown, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Luxurious, Cozy Beauty 10 min from Downtown Chicago

Luxurious, Cozy Beauty 10 min from Downtown Chicago is a apartment in Boystown, 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 $1,222.

From$175/night
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Karlov Inn | Stylish Chicago 2BR Retreat - Boystown, IL

Karlov Inn | Stylish Chicago 2BR Retreat

Apartment, Boystown

Karlov Inn · Stylish Chicago 2BR Retreat is a apartment in Boystown, with pet-friendly space, room for a group, and a quieter setting. This stay gives travelers a comfortable base for…

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About Karlov Inn | Stylish Chicago 2BR Retreat

Karlov Inn · Stylish Chicago 2BR Retreat is a apartment in Boystown, 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: hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,855.

From$265/night
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W2 - ❤️ New and Clean! Big Apartment with Parking - Boystown, IL

W2 - ❤️ New and Clean! Big Apartment with Parking

Apartment, Boystown

W2 - ❤️ New and Clean! Big Apartment with Parking is a apartment in Boystown, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About W2 - ❤️ New and Clean! Big Apartment with Parking

W2 - ❤️ New and Clean! Big Apartment with Parking is a apartment in Boystown, 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 $2,434.

From$348/night
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W3 - Spacious 2BR Apt + Free On-site Parking - Boystown, IL

W3 - Spacious 2BR Apt + Free On-site Parking

Apartment, Boystown

W3 - Spacious 2BR Apt + Free On-site Parking is a apartment in Boystown, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About W3 - Spacious 2BR Apt + Free On-site Parking

W3 - Spacious 2BR Apt + Free On-site Parking is a apartment in Boystown, 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 $2,443.

From$349/night
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Best Boystown, IL vacation rentals with a kitchen

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

Elegantly Designed 1BR Right Next to Beach - Boystown, IL

Elegantly Designed 1BR Right Next to Beach

Apartment, Boystown

Elegantly Designed 1BR Right Next to Beach is a apartment in Boystown, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Elegantly Designed 1BR Right Next to Beach

Elegantly Designed 1BR Right Next to Beach is a apartment in Boystown, with easy beach 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,560.

From$223/night
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Cozy apartment with AC and WiFi in awesome Chicago - Boystown, IL

Cozy apartment with AC and WiFi in awesome Chicago

Apartment, Boystown

Cozy apartment with AC and WiFi in awesome Chicago is a apartment in Boystown, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago is a apartment in Boystown, 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, gym, and dryer.

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

From$240/night
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House 5863 - Chicago Bed and Breakfast - Boystown, IL

House 5863 - Chicago Bed and Breakfast

B & B, Boystown

House 5863 - Chicago Bed and Breakfast is a b & b in Boystown, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast is a b & b in Boystown, 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 breakfast, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,178.

From$244/night
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The Bright Retreat in Andersonville - Boystown, IL

The Bright Retreat in Andersonville

Condo, Boystown

The Bright Retreat in Andersonville is a condo in Boystown, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About The Bright Retreat in Andersonville

The Bright Retreat in Andersonville is a condo in Boystown, 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,867.

From$267/night
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Our Favorite Family-Friendly Vacation Rentals in Boystown, IL

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

The Oak Park Loft - Boystown, IL

The Oak Park Loft

Apartment, Boystown

The Oak Park Loft is a apartment in Boystown, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

Read more

About The Oak Park Loft

The Oak Park Loft is a apartment in Boystown, 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, free wifi, parking, free parking, and family friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,036.

From$240/night
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Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field - Boystown, IL

Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field

Apartment, Boystown

Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field is a apartment in Boystown, with kitchen access and room for a group. This stay gives travelers a comfortable base…

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About Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field

Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field is a apartment in Boystown, 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,106.

From$301/night
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Comfy 2BR Family Haven with Skyline Views Near McCormick Place & Museums - Boystown, IL

Comfy 2BR Family Haven with Skyline Views Near McCormick Place & Museums

Apartment, Boystown

Comfy 2BR Family Haven with Skyline Views Near McCormick Place & Museums is a apartment in Boystown, with kitchen access and room for a group. This stay gives travelers a comfortable base…

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About Comfy 2BR Family Haven with Skyline Views Near McCormick Place & Museums

Comfy 2BR Family Haven with Skyline Views Near McCormick Place & Museums is a apartment in Boystown, 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,178.

From$311/night
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McCormick 2BR Family Retreat Near Museum Campus & Soldier Field - Boystown, IL

McCormick 2BR Family Retreat Near Museum Campus & Soldier Field

Apartment, Boystown

McCormick 2BR Family Retreat Near Museum Campus & Soldier Field is a apartment in Boystown, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About McCormick 2BR Family Retreat Near Museum Campus & Soldier Field

McCormick 2BR Family Retreat Near Museum Campus & Soldier Field is a apartment in Boystown, 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 $2,437.

From$348/night
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