Vacation rentals in Winnetka, IL

Best vacation rentals and Airbnb offers in Winnetka, IL

Studio | Free Breakfast! Heated Indoor Pool

Apartment, Winnetka

Studio · Free Breakfast! Heated Indoor Pool is a apartment in Winnetka, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Studio | Free Breakfast! Heated Indoor Pool

Studio · Free Breakfast! Heated Indoor Pool is a apartment in Winnetka, 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 $1,013.

From$145/night

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Free Breakfast Buffet at this Staybridge Studio! Indoor Pool, Gym, 24h Business Center!

Apartment, Winnetka

Free Breakfast Buffet at this Staybridge Studio! Indoor Pool, Gym, 24h Business Center! is a apartment in Winnetka, with pool access, parking, and kitchen access. This stay gives travelers…

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About Free Breakfast Buffet at this Staybridge Studio! Indoor Pool, Gym, 24h Business Center!

Free Breakfast Buffet at this Staybridge Studio! Indoor Pool, Gym, 24h Business Center! is a apartment in Winnetka, 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 $1,052.

From$150/night

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In \"The Glen\" Business District. Free Breakfast. Indoor Pool. Studio at Staybridge.

Apartment, Winnetka

In \"The Glen\" Business District. Free Breakfast. Indoor Pool. Studio at Staybridge. is a apartment in Winnetka, with pool access and kitchen access. This stay gives travelers a…

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About In \"The Glen\" Business District. Free Breakfast. Indoor Pool. Studio at Staybridge.

In \"The Glen\" Business District. Free Breakfast. Indoor Pool. Studio at Staybridge. is a apartment in Winnetka, 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 $1,052.

From$150/night

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Vintage Escape 1BR Two Blocks Away From Beach

Holiday Home, Winnetka

Vintage Escape 1BR Two Blocks Away From Beach is a holiday home in Winnetka, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Vintage Escape 1BR Two Blocks Away From Beach

Vintage Escape 1BR Two Blocks Away From Beach is a holiday home in Winnetka, with easy beach access, 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 washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,170.

From$167/night

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Vacation rentals with a pool in Winnetka, IL

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

Equipped Studio with Free Wi-Fi, Pool Access + Free Breakfast

Apartment, Winnetka

Equipped Studio with Free Wi-Fi, Pool Access + Free Breakfast is a apartment in Winnetka, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Equipped Studio with Free Wi-Fi, Pool Access + Free Breakfast

Equipped Studio with Free Wi-Fi, Pool Access + Free Breakfast is a apartment in Winnetka, 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 $1,010.

From$144/night

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Pool Access + Daily Free Breakfast Included!

Apartment, Winnetka

Pool Access + Daily Free Breakfast Included! is a apartment in Winnetka, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Pool Access + Daily Free Breakfast Included!

Pool Access + Daily Free Breakfast Included! is a apartment in Winnetka, 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 $1,010.

From$144/night

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

Condo, Winnetka

Great for Business Travel! Equipped King Suite with Pool Access + Free Breakfast is a condo in Winnetka, 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 Winnetka, 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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Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge

Apartment, Winnetka

Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge is a apartment in Winnetka, with pool access and kitchen access. This stay gives travelers a comfortable base…

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About Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge

Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge is a apartment in Winnetka, 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, kitchen, with kitchen, and gym.

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

From$265/night

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Vacation rentals with parking in Winnetka, IL

Find vacation rentals that make arriving by car easier.

1BR Modern Retreat w/ Free Parking Near Airport

Apartment, Winnetka

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

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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 Winnetka, 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 $1,417.

From$202/night

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Elegantly Designed 1BR Right Next to Beach

Apartment, Winnetka

Elegantly Designed 1BR Right Next to Beach is a apartment in Winnetka, 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 Winnetka, 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 $1,505.

From$215/night

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Chic 2BR Retreat Near O’Hare + Free Parking

Apartment, Winnetka

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

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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 Winnetka, 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 $1,531.

From$219/night

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Luxury stay walking distance to Metra, El, the Lake, and Northwestern

Holiday Home, Winnetka

Luxury stay walking distance to Metra, El, the Lake, and Northwestern is a holiday home in Winnetka, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Luxury stay walking distance to Metra, El, the Lake, and Northwestern

Luxury stay walking distance to Metra, El, the Lake, and Northwestern is a holiday home in Winnetka, 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 $1,545.

From$221/night

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Pet-friendly vacation rentals in Winnetka, IL

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

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

Apartment, Winnetka

Studio 6 Vernon Hills · ADA Queen bed,RI Shower,Nsmk · Kitchen is a apartment in Winnetka, 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 Winnetka, 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 $751.

From$107/night

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

Apartment, Winnetka

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

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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 Winnetka, 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

Apartment, Winnetka

1 King Bed · Non-Smoking, Kitchen, Shower is a apartment in Winnetka, 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 Winnetka, 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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Cozy 2 bed Apt- 2 train stops to the Naval Base!

Apartment, Winnetka

Cozy 2 bed Apt- 2 train stops to the Naval Base! is a apartment in Winnetka, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy 2 bed Apt- 2 train stops to the Naval Base!

Cozy 2 bed Apt- 2 train stops to the Naval Base! is a apartment in Winnetka, 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 $1,404.

From$201/night

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Vacation rentals with a kitchen in Winnetka, IL

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

Peaceful Norwood Nest- elevated comfort! Walkable, near O'Hare

Apartment, Winnetka

Peaceful Norwood Nest- elevated comfort! Walkable, near O'Hare is a apartment in Winnetka, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Peaceful Norwood Nest- elevated comfort! Walkable, near O'Hare

Peaceful Norwood Nest- elevated comfort! Walkable, near O'Hare is a apartment in Winnetka, 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 $1,328.

From$190/night

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Chic and Cozy Getaway near Loyola Park

Apartment, Winnetka

Chic and Cozy Getaway near Loyola Park is a apartment in Winnetka, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Chic and Cozy Getaway near Loyola Park

Chic and Cozy Getaway near Loyola Park is a apartment in Winnetka, 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,388.

From$198/night

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Spacious and Newly Renovated 1BR Next to the Beach

Apartment, Winnetka

Spacious and Newly Renovated 1BR Next to the Beach is a apartment in Winnetka, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Spacious and Newly Renovated 1BR Next to the Beach

Spacious and Newly Renovated 1BR Next to the Beach is a apartment in Winnetka, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,556.

From$222/night

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Exquisite Rogers Park 1 bedroom, 1 bath Apartment Near Evanston

Apartment, Winnetka

Exquisite Rogers Park 1 bedroom, 1 bath Apartment Near Evanston is a apartment in Winnetka, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Exquisite Rogers Park 1 bedroom, 1 bath Apartment Near Evanston

Exquisite Rogers Park 1 bedroom, 1 bath Apartment Near Evanston is a apartment in Winnetka, 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 $2,129.

From$241/night

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Family-friendly vacation rentals in Winnetka, IL

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

Family Home in Chicago-O'Hare

Holiday Home, Winnetka

Family Home in Chicago-O'Hare is a holiday home in Winnetka, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Family Home in Chicago-O'Hare

Family Home in Chicago-O'Hare is a holiday home in Winnetka, 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 $2,594.

From$371/night

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

Cottage, Winnetka

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

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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 Winnetka, 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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1 Mi to Metra: Estate w/ Theater, Game Room & More

Cottage, Winnetka

1 Mi to Metra: Estate w/ Theater, Game Room & More is a cottage in Winnetka, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 1 Mi to Metra: Estate w/ Theater, Game Room & More

1 Mi to Metra: Estate w/ Theater, Game Room & More is a cottage in Winnetka, 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 $10,027.

From$1,221/night

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Family Friendly, Lovely 6 Bd Retreat w/ Game Room, Back Deck & Bar

Holiday Home, Winnetka

Family Friendly, Lovely 6 Bd Retreat w/ Game Room, Back Deck & Bar is a holiday home in Winnetka, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable…

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About Family Friendly, Lovely 6 Bd Retreat w/ Game Room, Back Deck & Bar

Family Friendly, Lovely 6 Bd Retreat w/ Game Room, Back Deck & Bar is a holiday home in Winnetka, with outdoor 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,076.

From$1,297/night

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