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Holiday houses in Skokie

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Top-rated holiday 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

20–27 Mar

$257 NZD per night

Guest favourite

Guest suite in Chicago

4.96 out of 5 average rating, 102 reviews

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

Send an inquiry before requesting booking. Quiet, tree-lined urban getaway. Separate lower level unit located in a Chicago-style bungalow near wonderful neighborhoods and restaurants. Extremely comfortable and cozy, this spot will make you forget you are in the city. Diverse restaurants to whet your appetite- Mexican, Ethiopian, Jamaican, Jewish and Indian. Take long walks to the beach (15min), to the numerous parks and or festivals and celebrations. Or cozy up to read, nap or watch a movie.

3–10 Mar

$243 NZD per night

Guest favourite

Apartment in Evanston

4.94 out of 5 average rating, 116 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 18 min walk for trains to city, 5 min drive to lake. Wifi

4–11 Sep

$317 NZD per night

Guest favourite

Guesthouse in Evanston

4.98 out of 5 average rating, 207 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.

26 Apr – 3 May

$347 NZD per night

Guest favourite

Apartment in Evanston

4.97 out of 5 average rating, 408 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.

28 Apr – 5 May

$342 NZD per night

Guest favourite

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!

28 Feb – 7 Mar

$296 NZD per night

Guest favourite

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 !

4–11 Mar

$184 NZD per night

Guest favourite

Apartment in Skokie

4.91 out of 5 average rating, 534 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!

21–28 Nov

$237 NZD per night

Guest favourite

Guest suite in Highland Park

4.96 out of 5 average rating, 111 reviews

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

Charming little house in Highland Park. In-law suite is in the basement and has it's own full size kitchen bathroom. We live up-stairs with our 3 little dogs so we will be available if you need anything during your stay. The in-law suite is set up like a studio and has one queen bed and a separate closet area. Please note- the suite is in the basement. You have shared use of the deck/yard

15–22 Oct

$235 NZD per night

Guest favourite

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.

20–27 Oct

$215 NZD per night

Guest favourite

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.

30 Mar – 6 Apr

$340 NZD 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.

10–17 Oct

$288 NZD per night

Holiday rentals for every style

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Popular amenities for Skokie holiday 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 holiday rentals in Skokie

Guest favourite

Guest suite in Chicago

5.0 out of 5 average rating, 296 reviews

Private Lincoln Square one bed+bath studio apt.

18–25 Oct

$306 NZD per night

Guest favourite

Apartment in Chicago

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

28 Jul – 4 Aug

$239 NZD per night

Guest favourite

Apartment in Evanston

4.86 out of 5 average rating, 186 reviews

Charming English Garden Unit

13–20 Jan

$231 NZD per night

Guest favourite

Apartment in Arlington Heights

4.99 out of 5 average rating, 115 reviews

Ideal Location in Awesome Heights

$208 NZD per night

Guest favourite

Apartment in Wilmette

4.86 out of 5 average rating, 119 reviews

Downtown Wilmette Micro Studio

28 Jun – 5 Jul

$262 NZD per night

Guest favourite

Apartment in Evanston

4.95 out of 5 average rating, 214 reviews

Crisp and Clean 2BD Getaway Near Downtown Evanston

9–16 Aug

$436 NZD per night

Guest favourite

Home in Wilmette

4.98 out of 5 average rating, 92 reviews

Unique porcelain-enamel paneled "Lustron" home

22–29 Oct

$308 NZD per night

Guest favourite

Condo in Skokie

4.93 out of 5 average rating, 15 reviews

Free Parking Balcony, Weekly 5% & Monthly 10% Off

25 Jun – 2 Jul

$292 NZD per night

Quick stats about holiday rentals in Skokie

Total rentals
130 properties
Wi-Fi availability
120 properties include access to Wi-Fi
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

Destinations to explore