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Holiday homes in Skokie You’ll Love

Top-Rated Skokie Holiday homes for Every Budget and Style!

Looking for a holiday home in Skokie (Illinois)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $51.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Skokie.

We found 14 Holiday-homes in Skokie and the surrounding area (within 40 miles)

Windy City Getaway - 3BR 2BA Chicago Townhouse home in Chicago, USA

Windy City Getaway - 3BR 2BA Chicago Tow...

Holiday home in Chicago near Skokie, Illinois
Windy City Getaway - 3BR 2BA Chicago Townhouse home is located in Chicago, just 5 miles from Wrigley Field and 6.1 miles from Lincoln Park Zoo.
  • Parking

Exceptional 2 Reviews 9.5

from $307.60 Show details »

Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub in Chicago, USA

Historic Home with Outdoor Hot Tub Near...

Holiday home in Chicago near Skokie, Illinois , 3742 N. Keeler Avenue, Chicago,
A recently renovated vacation home, Historic Home with Outdoor Hot Tub Near Downtown in Public Transportation Hub offers accommodations in Chicago.
  • Parking
  • Family rooms
  • Kids' outdoor play equipment

Superb 8 Reviews 9.4

from $63.00 Show details »

Chicago Big House in Chicago, USA

Chicago Big House

Holiday home in Chicago near Skokie, Illinois , 4511 North Melvina Avenue
Chicago Big House is located in Chicago, just 7.1 miles from Wrigley Field and 8.8 miles from Lincoln Park Zoo.
  • Parking
  • Pets allowed

no reviews

from $82.00 Show details »

A terrific house for a large group. in Chicago, USA

A terrific house for a large group.

Holiday home in Chicago near Skokie, Illinois , 4511 North Melvina Avenue
A terrific house for a large group.
  • Parking
  • Pets allowed
  • Family rooms

Fabulous 6 Reviews 8.8

from $69.00 Show details »

Awesome Chicago Home with Game Room, Deck and Yard! in Chicago, USA

Awesome Chicago Home with Game Room, Dec...

Holiday home in Chicago near Skokie, Illinois
6.1 miles from Loyola University Chicago in Chicago, Awesome Chicago Home with Game Room, Deck and Yard! offers accommodations with access to a fitnes...
  • Parking
  • Bar

no reviews

from $94.00 Show details »

Elegant Hideaway in the Heart of Andersonville in Chicago, USA

Elegant Hideaway in the Heart of Anderso...

Holiday home in Chicago near Skokie, Illinois , 5119 N Ashland Ave
Elegant Hideaway in the Heart of Andersonville is located in Chicago, just 1.3 miles from Foster Beach and 1.7 miles from Montrose Beach.
  • Family rooms

no reviews

from $78.00 Show details »

Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find in Chicago, USA

Northside FAMLYNEST Lincoln Sq 4BR 2BA 2...

Holiday home in Chicago near Skokie, Illinois , 2713 West Balmoral Avenue
Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find is a recently renovated vacation home in Chicago where guests can make the most of the garden and ...
  • Parking
  • Pets allowed
  • Family rooms
  • Kids' outdoor play equipment

Exceptional 42 Reviews 9.7

from $301.95 Show details »

Stylish Chicago Retreat, Walk to Loyola University in Chicago, USA

Stylish Chicago Retreat, Walk to Loyola...

Holiday home in Chicago near Skokie, Illinois
Stylish Chicago Retreat, Walk to Loyola University is located in Chicago, just a 8-minute walk from Loyola University Chicago and 3.5 miles from Wrigl...
  • Parking
  • Pets allowed

Exceptional 2 Reviews 9.5

from $371.82 Show details »

Stunning home in Skokie in Skokie, USA

Stunning home in Skokie

Holiday home in Skokie, Illinois , 7716 Tripp Avenue
Stunning home in Skokie offers accommodations in Skokie, 5 miles from Loyola University Chicago and 7.6 miles from Wrigley Field.
  • Parking
  • Pets allowed

Exceptional 7 Reviews 9.6

from $254.73 Show details »

Urban Oasis - Kid Friendly - Quiet Street in Skokie, USA

Urban Oasis - Kid Friendly - Quiet Stree...

Holiday home in Skokie, Illinois , 8311 Kolmar Avenue
Providing a garden, Urban Oasis - Kid Friendly - Quiet Street features accommodations in Skokie.
  • Parking
  • Pets allowed
  • Family rooms

Superb 8 Reviews 9.2

from $261.56 Show details »

Spacious 2 bedroom home in Niles, Illinois with office, full kitchen and 2 baths in Niles, USA

Spacious 2 bedroom home in Niles, Illino...

Holiday home in Niles near Skokie, Illinois , 8509 North Ozanam Avenue
Providing a bar, Spacious 2 bedroom home in Niles, Illinois with office, full kitchen and 2 baths features accommodations in Niles.
  • Parking
  • Pets allowed
  • Bar
  • Family rooms

no reviews

from $71.00 Show details »

Rest and Relaxation with Game Room Morton Grove IL 3 BR House in Morton Grove, USA

Rest and Relaxation with Game Room Morto...

Holiday home in Morton Grove near Skokie, Illinois , 6028 Crain Street
Rest and Relaxation with Game Room Morton Grove IL 3 BR House offers accommodations in Morton Grove, 12 miles from Wrigley Field and 14 miles from Lin...
  • Parking
  • Pets allowed

no reviews

from $450.24 Show details »

Suburban 4bed2bath Oasis- freshly updated in Morton Grove, USA

Suburban 4bed2bath Oasis- freshly update...

Holiday home in Morton Grove near Skokie, Illinois , 7125 Simpson St
Suburban 4bed2bath Oasis- freshly updated is located in Morton Grove, just 11 miles from Loyola University Chicago and 13 miles from Wrigley Field.
  • Parking

no reviews

from $87.00 Show details »

Charming Contemporary Family Home home in Glenview, USA

Charming Contemporary Family Home home

Holiday home in Glenview near Skokie, Illinois
Charming Contemporary Family Home home is located in Glenview, just 12 miles from Loyola University Chicago and 14 miles from Wrigley Field.
  • Parking
  • Pets allowed

Fabulous 3 Reviews 8.7

from $387.78 Show details »

Number of Holiday homes in Skokie 14
Number of guest ratings 2,240
Average price per night $246.00
Lowest price per night $51,00
Highest price per night $1.440,48

Top 10 Cheapest Holiday-homes in Skokie

Discover the Cheapest Holiday-homes in Skokie – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Skokie

Check out the Most Booked Holiday-homes in Skokie – Based on Guest Popularity.

Holiday homes in Skokie (Illinois), comfortable and familiar

Staying in a holiday or vacation home in Skokie can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Skokie for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Skokie should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com