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Vacation rentals in Skokie

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Top-rated vacation rentals in Skokie

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Apartment in Park Ridge

4.79 out of 5 average rating, 321 reviews

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level Condo one bedroom one bath. The Condo is very large for a one bedroom. Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. Perfect place to relax Perfect and safe place to rest . 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10 min from Chicago outlets etc. It is not a party room . No parties or large gathering .... Garden Apartment

Jan 9 – 16

€ 146 per night

Apartment in Evanston

4.95 out of 5 average rating, 115 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

Welcome to the sunny, spacious, 2nd floor full apartment of our 1920's home! While we live downstairs, the whole upstairs space is yours. Living room, dining room, kitchen w/ DW, full bath, 2 BR, charming sitting room w/ electric FP. Perfect for up to 5 guests. The vintage kitchen is well supplied including Keurig. LR has sofa-bed, love seat, games & 50" ROKU smart TV to connect to streaming services. Kid stuff inc. pk & play Easy 20 min walk for trains to city, 5 min drive to lake. Wifi

Sep 7 – 14

€ 182 per night

Guesthouse in Evanston

4.98 out of 5 average rating, 202 reviews

Cottage in a Garden

Enjoy the serenity of our secret garden from your private guest house. Enjoy privacy on the covered sun porch. Watch butterflies float by in the pollinator garden. Listen to evening quiet on the patio overlooking the garden. Spin some records from the eclectic collection. Stroll the leafy neighborhood. Stop for a beer at award-winning Temperance Brewery. 5 minute walk to Divvy bike station gives you access to all of Chicago and CTA/Metra train. Short ride to lakefront, Northwestern, downtown.

Mar 5 – 12

€ 167 per night

Guest suite in Chicago

4.98 out of 5 average rating, 111 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

Sep 13 – 20

€ 115 per night

Guest suite in Evanston

4.97 out of 5 average rating, 213 reviews

A guest suite centrally located, but so quiet...

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my guest suite w/private kitchen, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

Nov 29 – Dec 6

€ 120 per night

Apartment in Wilmette

4.86 out of 5 average rating, 119 reviews

Downtown Wilmette Micro Studio

During this time, we are taking extra precautionary measures to ensure our guests safety. Cute and private micro studio in phenomenal downtown Wilmette location. Steps from all local restaurants, shopping, and the Metra station. Walkable to Gillson Beach and the Linden CTA stop. Enter through the front gate to an open & shared yard with private, single access to the unit. Pets OK with additional pet fee (some breed / weight restrictions).

Jun 21 – 28

€ 142 per night

Apartment in Evanston

4.95 out of 5 average rating, 210 reviews

Crisp and Clean 2BD Getaway Near Downtown Evanston

My top floor, 2 bedroom home sits in a quiet cul-de-sac, about a mile from downtown Evanston; a 15 min walk to the Dempster Purple line station, which brings you right into Chicago. Northwestern and Loyola are nearby for a visit too! The area has wonderful lakeside parks and beaches, so no matter the time of year, you'll appreciate the natural beauty! Grocery stores, coffee shops, and restaurants are within walking distance as well.

Nov 17 – 24

€ 191 per night

Guest suite in Evanston

4.83 out of 5 average rating, 326 reviews

Huge, cozy one bedroom semi-basement apartment

1000 SF Close both to Chicago area and the lake and the suburbs. It has a side separate entrance from the main house. One bedroom with one queen bed. A pull out couch too. A fully equipped kitchen. One full bathroom with a shower , no tub. A cozy living room with TV. This propery has surveillance cameras . Strict rules will be applied to violation of maximum capacity of 4 people. The place is not rented for parties !

Mar 13 – 20

€ 104 per night

Apartment in Skokie

4.91 out of 5 average rating, 531 reviews

Cozy Garden Unit in Quiet Neighborhood

A cozy garden unit in the heart of skokie, off of a quiet residential street with plenty of street parking. Just a mile away from the Skokie-Dempster Yellow line train that leads to downtown Chicago, and within a mile from Old Orchard Mall and plenty of great eateries such as: Chick-fil-A, Portillo's, Culver's, Oberwies, Kaufman's Bagel, and more. 15 minutes away from Evanston and the Beautiful Lake Michigan shoreline!

Apr 7 – 14

€ 142 per night

Guest suite in Chicago

4.94 out of 5 average rating, 177 reviews

Lincoln Square In-laws Suite: Private Entrance

Garden apartment room with private entrance and ensuite bathroom. All the amenities you'll need for either a work trip, city sightseeing, or just a comfy bed. Located in the vibrant Lincoln Square neighborhood. Only minutes away from the train. Fast wifi, and a large desk for working away from home. P.S. You will most likely find a few beers from a Chicago brewery in the fridge.

Sep 16 – 23

€ 123 per night

Apartment in Skokie

4.97 out of 5 average rating, 120 reviews

Charming Apt.Fully Equipped Prk.Inc 12 min 2 Lake

Newly renovated, 2-bedroom apartment. New appliances. Relaxing atmosphere. Walking distance to shopping, restaurants, grocery, train station, etc. Nice and quiet neighborhood. Central air & heating, washer & dryer, iron & ironing board, shampoo, conditioner, body wash, hair dryer, coffee maker, toaster, large fridge. All kitchen utensils available for use.

Aug 22 – 29

€ 182 per night

Apartment in Evanston

4.83 out of 5 average rating, 215 reviews

Adorable 1BR apartment near Northwestern

Cozy and comfortable one bedroom apartment with full kitchen and updated bath. Recently re-decorated with fresh carpet, paint and new queen bed. Located on the second floor of a single family 2-flat style home in a quiet, residential neighborhood. Ample, free street parking. One additional person can be accommodated with blow-up mattress.

Sep 22 – 29

€ 163 per night

Vacation rentals for every style

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Popular amenities for Skokie vacation rentals

Free parking on premises

Air conditioning

Stay near Skokie's top sights

Westfield Old Orchard18 locals recommend

Lincolnwood Town Center12 locals recommend

Illinois Holocaust Museum & Education Center6 locals recommend

Pita Inn10 locals recommend

AMC Village Crossing 189 locals recommend

Maggiano's Little Italy3 locals recommend

Other great vacation rentals in Skokie

Guest suite in Skokie

4.86 out of 5 average rating, 148 reviews

Adorable studio style unit - Self check in ⚡️

Jul 31 – Aug 7

€ 210 per night

Guest suite in Chicago

5.0 out of 5 average rating, 293 reviews

Private Lincoln Square one bed+bath studio apt.

Sep 17 – 24

€ 174 per night

Apartment in Chicago

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

Jul 9 – 16

€ 141 per night

Guest suite in Chicago

4.96 out of 5 average rating, 102 reviews

1BR Historic Rogers Park/West Ridge unit- Sleeps 4

Mar 22 – 29

€ 138 per night

Guest suite in Chicago

4.93 out of 5 average rating, 352 reviews

Peaceful Portage Park Apartment

Jan 15 – 22

€ 137 per night

Apartment in Chicago

4.88 out of 5 average rating, 104 reviews

LAKESIDE PIED `A TERRE STEPS TO BEACH

Jan 23 – 30

€ 142 per night

Home in Wilmette

4.98 out of 5 average rating, 92 reviews

Unique porcelain-enamel paneled "Lustron" home

Sep 23 – 30

€ 174 per night

Home in Skokie

4.87 out of 5 average rating, 86 reviews

A+amazing beauty, entire 2 BR Skokie historic stay

Mar 23 – 30

€ 111 per night

Quick stats about vacation rentals in Skokie

Total rentals
130 properties
Wifi availability
120 properties include access to wifi
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
6.2K reviews

Frequently Asked Questions

Are there family-friendly vacation rentals in Skokie?
Skokie has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Skokie?
Yes! Work meets play with ease at over 80 vacation rentals in Skokie featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Skokie have free parking?
Absolutely! We offer over 50 house rentals with free parking in Skokie. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Skokie?
Four-legged friends are welcome in Skokie. Choose from more than 40 vacation rentals for guests traveling with pets.
Do apartment rentals in Skokie have a kitchen?
Absolutely! We offer over 30 apartment rentals with a kitchen in Skokie. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in condo rentals in Skokie?
Experience the best of Skokie with our condo rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Skokie have air conditioning?
Absolutely! We offer over 30 apartment rentals with air conditioning in Skokie. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Condo Rentals in Skokie?
Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

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