Vacation rentals in Highland Park, IL

97 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Highland Park, IL

Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen - Highland Park, IL

Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen

Apartment, Highland Park

Studio 6 Vernon Hills · ADA Queen bed,RI Shower,Nsmk · Kitchen is a apartment in Highland Park, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Studio 6 Vernon Hills|ADA Queen bed,RI Shower,Nsmk|Kitchen

Studio 6 Vernon Hills · ADA Queen bed,RI Shower,Nsmk · Kitchen is a apartment in Highland Park, 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 $752.

From$107/night
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Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen - Highland Park, IL

Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

Apartment, Highland Park

Studio 6 Vernon Hills · Relax Queen Bed,Nsmk · Kitchen is a apartment in Highland Park, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a…

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About Studio 6 Vernon Hills|Relax Queen Bed,Nsmk|Kitchen

Studio 6 Vernon Hills · Relax Queen Bed,Nsmk · Kitchen is a apartment in Highland Park, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $752.

From$107/night
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1 King Bed | Non-Smoking, Kitchen, Shower - Highland Park, IL

1 King Bed | Non-Smoking, Kitchen, Shower

Apartment, Highland Park

1 King Bed · Non-Smoking, Kitchen, Shower is a apartment in Highland Park, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed · Non-Smoking, Kitchen, Shower is a apartment in Highland Park, 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 $786.

From$112/night
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1 King Bed | Non-Smoking, Kitchen - Highland Park, IL

1 King Bed | Non-Smoking, Kitchen

Apartment, Highland Park

1 King Bed · Non-Smoking, Kitchen is a apartment in Highland Park, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 1 King Bed | Non-Smoking, Kitchen

1 King Bed · Non-Smoking, Kitchen is a apartment in Highland Park, 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 $801.

From$114/night
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Browse Vacation Rentals with a Pool in Highland Park, IL

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

Great for Business Travel! Equipped King Suite with Pool Access + Free Breakfast - Highland Park, IL

Great for Business Travel! Equipped King Suite with Pool Access + Free Breakfast

Condo, Highland Park

Great for Business Travel! Equipped King Suite with Pool Access + Free Breakfast is a condo in Highland Park, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Great for Business Travel! Equipped King Suite with Pool Access + Free Breakfast

Great for Business Travel! Equipped King Suite with Pool Access + Free Breakfast is a condo in Highland Park, 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 $1,157.

From$165/night
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King Suite in \"The Glen\" District. Free Breakfast Daily. Indoor Pool - Highland Park, IL

King Suite in \"The Glen\" District. Free Breakfast Daily. Indoor Pool

Condo, Highland Park

King Suite in \"The Glen\" District. Free Breakfast Daily. Indoor Pool is a condo in Highland Park, with pool access, parking, and kitchen access. This stay gives travelers a comfortable…

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About King Suite in \"The Glen\" District. Free Breakfast Daily. Indoor Pool

King Suite in \"The Glen\" District. Free Breakfast Daily. Indoor Pool is a condo in Highland Park, 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 $1,377.

From$197/night
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Guests Get Free Breakfast Daily! In \"The Glen\" District. Indoor Pool | Staybridge Suites - Highland Park, IL

Guests Get Free Breakfast Daily! In \"The Glen\" District. Indoor Pool | Staybridge Suites

Condo, Highland Park

Guests Get Free Breakfast Daily! In \"The Glen\" District. Indoor Pool · Staybridge Suites is a condo in Highland Park, with pool access and kitchen access. This stay gives travelers a…

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About Guests Get Free Breakfast Daily! In \"The Glen\" District. Indoor Pool | Staybridge Suites

Guests Get Free Breakfast Daily! In \"The Glen\" District. Indoor Pool · Staybridge Suites is a condo in Highland Park, 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 $1,443.

From$206/night
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Great for Business Travel! Equipped Suite with Pool Access + Free Breakfast - Highland Park, IL

Great for Business Travel! Equipped Suite with Pool Access + Free Breakfast

Condo, Highland Park

Great for Business Travel! Equipped Suite with Pool Access + Free Breakfast is a condo in Highland Park, with pool access and kitchen access. This stay gives travelers a comfortable base…

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About Great for Business Travel! Equipped Suite with Pool Access + Free Breakfast

Great for Business Travel! Equipped Suite with Pool Access + Free Breakfast is a condo in Highland Park, 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 $1,663.

From$238/night
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Best Highland Park, IL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Always a Great Idea To Unwind, Kitchen, Pets Allowed, Private Parking - Highland Park, IL

Always a Great Idea To Unwind, Kitchen, Pets Allowed, Private Parking

Apartment, Highland Park

Always a Great Idea To Unwind, Kitchen, Pets Allowed, Private Parking is a apartment in Highland Park, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Always a Great Idea To Unwind, Kitchen, Pets Allowed, Private Parking

Always a Great Idea To Unwind, Kitchen, Pets Allowed, Private Parking is a apartment in Highland Park, 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, hot tub, free wifi, pet friendly, and pets friendly.

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

From$128/night
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Enjoy a Hassle-Free Stay, Parking, Kitchen, Pet-Friendly Property - Highland Park, IL

Enjoy a Hassle-Free Stay, Parking, Kitchen, Pet-Friendly Property

Apartment, Highland Park

Enjoy a Hassle-Free Stay, Parking, Kitchen, Pet-Friendly Property is a apartment in Highland Park, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Enjoy a Hassle-Free Stay, Parking, Kitchen, Pet-Friendly Property

Enjoy a Hassle-Free Stay, Parking, Kitchen, Pet-Friendly Property is a apartment in Highland Park, 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, hot tub, free wifi, pet friendly, and pets friendly.

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

From$128/night
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Waukegan History Museum Tour! Private Parking, Near O'Plaine Park - Highland Park, IL

Waukegan History Museum Tour! Private Parking, Near O'Plaine Park

Apartment, Highland Park

Waukegan History Museum Tour! Private Parking, Near O'Plaine Park is a apartment in Highland Park, with pet-friendly space and parking. This stay gives travelers a comfortable base for…

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About Waukegan History Museum Tour! Private Parking, Near O'Plaine Park

Waukegan History Museum Tour! Private Parking, Near O'Plaine Park is a apartment in Highland Park, with pet-friendly space 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, hot tub, free wifi, pet friendly, and pets friendly.

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

From$128/night
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Cozy 1-Bedroom House in Tranquil Skokie With Parking - Highland Park, IL

Cozy 1-Bedroom House in Tranquil Skokie With Parking

Holiday Home, Highland Park

Cozy 1-Bedroom House in Tranquil Skokie With Parking is a holiday home in Highland Park, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Cozy 1-Bedroom House in Tranquil Skokie With Parking

Cozy 1-Bedroom House in Tranquil Skokie With Parking is a holiday home in Highland Park, 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 $1,511.

From$216/night
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Best Pet-Friendly Vacation Rentals in Highland Park, IL

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

1BR Modern Retreat w/ Free Parking Near Airport - Highland Park, IL

1BR Modern Retreat w/ Free Parking Near Airport

Apartment, Highland Park

1BR Modern Retreat w/ Free Parking Near Airport is a apartment in Highland Park, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 1BR Modern Retreat w/ Free Parking Near Airport

1BR Modern Retreat w/ Free Parking Near Airport is a apartment in Highland Park, 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 $1,434.

From$205/night
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Modern 4BD 2BA Home Near Downtown / Metra - Highland Park, IL

Modern 4BD 2BA Home Near Downtown / Metra

Holiday Home, Highland Park

Modern 4BD 2BA Home Near Downtown / Metra is a holiday home in Highland Park, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Modern 4BD 2BA Home Near Downtown / Metra

Modern 4BD 2BA Home Near Downtown / Metra is a holiday home in Highland Park, 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: pet friendly, pets friendly, gym, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,093.

From$299/night
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Highwood Haven- 4 Bedroom Steps to Train station! - Highland Park, IL

Highwood Haven- 4 Bedroom Steps to Train station!

Apartment, Highland Park

Highwood Haven- 4 Bedroom Steps to Train station! is a apartment in Highland Park, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Highwood Haven- 4 Bedroom Steps to Train station!

Highwood Haven- 4 Bedroom Steps to Train station! is a apartment in Highland Park, 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 $2,483.

From$355/night
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Cozy Highwood Apt- 4 Bed 2 train stops to Naval Base! - Highland Park, IL

Cozy Highwood Apt- 4 Bed 2 train stops to Naval Base!

Apartment, Highland Park

Cozy Highwood Apt- 4 Bed 2 train stops to Naval Base! is a apartment in Highland Park, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Cozy Highwood Apt- 4 Bed 2 train stops to Naval Base!

Cozy Highwood Apt- 4 Bed 2 train stops to Naval Base! is a apartment in Highland Park, 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 $2,694.

From$385/night
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Best Highland Park, IL vacation rentals with a kitchen

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

Make Your Trip More Enjoyable! Kitchen, Pets Allowed, Private Parking - Highland Park, IL

Make Your Trip More Enjoyable! Kitchen, Pets Allowed, Private Parking

Apartment, Highland Park

Make Your Trip More Enjoyable! Kitchen, Pets Allowed, Private Parking is a apartment in Highland Park, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Make Your Trip More Enjoyable! Kitchen, Pets Allowed, Private Parking

Make Your Trip More Enjoyable! Kitchen, Pets Allowed, Private Parking is a apartment in Highland Park, 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,294.

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

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

Apartment, Highland Park

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

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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 Highland Park, 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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Chic 2BR Retreat Near O’Hare + Free Parking - Highland Park, IL

Chic 2BR Retreat Near O’Hare + Free Parking

Apartment, Highland Park

Chic 2BR Retreat Near O’Hare + Free Parking is a apartment in Highland Park, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Chic 2BR Retreat Near O’Hare + Free Parking

Chic 2BR Retreat Near O’Hare + Free Parking is a apartment in Highland Park, 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 $1,537.

From$220/night
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Charming Lake Forest Country Estate - Highland Park, IL

Charming Lake Forest Country Estate

Holiday Home, Highland Park

Charming Lake Forest Country Estate is a holiday home in Highland Park, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Charming Lake Forest Country Estate

Charming Lake Forest Country Estate is a holiday home in Highland Park, 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: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,461.

From$352/night
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Our Favorite Family-Friendly Vacation Rentals in Highland Park, IL

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

Light-filled 1bdrm garden apartment on golf course near Northwestern U. - Highland Park, IL

Light-filled 1bdrm garden apartment on golf course near Northwestern U.

Apartment, Highland Park

Light-filled 1bdrm garden apartment on golf course near Northwestern U. is a apartment in Highland Park, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Light-filled 1bdrm garden apartment on golf course near Northwestern U.

Light-filled 1bdrm garden apartment on golf course near Northwestern U. is a apartment in Highland Park, 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 $1,257.

From$180/night
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Roxan Cozy Corner Mundelene Sailor’s Welcome House/ Navel Family Retreat - Highland Park, IL

Roxan Cozy Corner Mundelene Sailor’s Welcome House/ Navel Family Retreat

Holiday Home, Highland Park

Roxan Cozy Corner Mundelene Sailor’s Welcome House/ Navel Family Retreat is a holiday home in Highland Park, with pet-friendly space, kitchen access, and room for a group. This stay gives…

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About Roxan Cozy Corner Mundelene Sailor’s Welcome House/ Navel Family Retreat

Roxan Cozy Corner Mundelene Sailor’s Welcome House/ Navel Family Retreat is a holiday home in Highland Park, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,753.

From$250/night
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Charming Family home near Great Lakes Naval Base! - Highland Park, IL

Charming Family home near Great Lakes Naval Base!

Holiday Home, Highland Park

Charming Family home near Great Lakes Naval Base! is a holiday home in Highland Park, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Charming Family home near Great Lakes Naval Base!

Charming Family home near Great Lakes Naval Base! is a holiday home in Highland Park, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,962.

From$280/night
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.The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining - Highland Park, IL

.The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining

Cottage, Highland Park

.The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining is a cottage in Highland Park, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About .The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining

.The Pleasant Hill Cottage. North Shore Beaches Ravinia Weddings Families Dining is a cottage in Highland Park, with pet-friendly space, easy beach 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,047.

From$721/night
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