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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, 322 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

Aug 23 – 30

G$30,425 GYD 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

Aug 31 – Sep 7

G$35,356 GYD per night

Guesthouse in Evanston

4.98 out of 5 average rating, 204 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.

Feb 7 – 14

G$31,710 GYD per night

Apartment in Arlington Heights

4.99 out of 5 average rating, 115 reviews

Ideal Location in Awesome Heights

Near the heart of downtown Arlington Heights and convenient to O’Hare. You can settle in at this cozy basement apartment with a super comfortable queen bed and all the amenities you’d need. Whether your visit to AH is for business or pleasure, city or suburbs, we look forward to hosting you. The private apartment works great for guests with a car or using public transit. Easy access to Metra station, AH restaurants, Des Plaines Theater, NW Community Hospital & Schaumburg Convention Center.

May 3 – 10

G$29,828 GYD per night

Apartment in Evanston

4.97 out of 5 average rating, 407 reviews

Charming, Sunny Apartment with Backyard Garden

House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.

Apr 3 – 10

G$32,974 GYD per night

Guest suite in Evanston

4.97 out of 5 average rating, 214 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!

Sep 23 – 30

G$21,729 GYD 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).

Jul 1 – 8

G$27,183 GYD per night

Apartment in Evanston

4.95 out of 5 average rating, 212 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.

Mar 31 – Apr 7

G$38,563 GYD per night

Guest suite in Evanston

4.83 out of 5 average rating, 327 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 !

Nov 13 – 20

G$19,227 GYD per night

Apartment in Skokie

4.91 out of 5 average rating, 533 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!

Feb 28 – Mar 7

G$27,582 GYD per night

Guest suite in Chicago

4.94 out of 5 average rating, 178 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 21 – 28

G$21,231 GYD 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 9 – 16

G$35,220 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

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Apartments

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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

Apartment in Evanston

4.97 out of 5 average rating, 177 reviews

Cheerful 2 bd apt in central Evanston w/ king bed

Dec 23 – 30

G$37,389 GYD per night

Guest suite in Chicago

4.96 out of 5 average rating, 102 reviews

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

Apr 21 – 28

G$23,131 GYD per night

Guest suite in Chicago

4.98 out of 5 average rating, 111 reviews

Gorgeous Studio 15 Minutes From Ohare!

Apr 22 – 29

G$19,339 GYD per night

Guest suite in Highland Park

4.96 out of 5 average rating, 111 reviews

Charming in-law suite w/ use of deck and yard

Oct 10 – 17

G$26,596 GYD per night

Apartment in Chicago

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

Jul 17 – 24

G$23,798 GYD per night

Apartment in Chicago

4.95 out of 5 average rating, 196 reviews

Free Parking & King Bed in Desirable Norwood Park!

Jul 24 – 31

G$28,534 GYD per night

Apartment in Evanston

4.86 out of 5 average rating, 186 reviews

Charming English Garden Unit

Jan 18 – 25

G$24,176 GYD per night

Apartment in Skokie

4.87 out of 5 average rating, 46 reviews

Fascinating 1BR Apt in Skokie near Leisure Center

Sep 28 – Oct 5

G$33,771 GYD 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 apartment rentals in Skokie have free parking?
Absolutely! We offer over 20 apartment 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 condo rentals in Skokie have a kitchen?
Absolutely! We offer over 10 condo 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 house rentals in Skokie have air conditioning?
Absolutely! We offer over 60 house rentals with air conditioning in Skokie. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Skokie?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with free parking, over 30 homes with wifi, over 30 homes with a kitchen, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore