Holiday houses in Skokie

4.97 out of 5 average rating, 153 reviews

Home in Wilmette

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

4.97 out of 5 average rating, 76 reviews

Luxe Limewash Getaway w/Sun Deck

Relax with the whole family at this peaceful place to stay! This retreat seamlessly blends classic charm with modernity. Enjoy a cozy living room, bonus piano space, and new bathrooms. Relax on the deck or explore nearby gems. Conveniently near highways, it's an ideal hub to explore Skokie, Evanston, Niles, Wilmette, Evanston, and Chicago. O'Hare Airport - 25 min drive Wrigley Field - 12 min drive Northwestern University - 9 min drive Loyola University - 9 min drive Starbucks ‬- 3 min drive

Superhost

5 out of 5 average rating, 4 reviews

Stokes Stay: Spacious 4BR/3BA

This beautifully updated 4-br, 3-ba home in the heart of Skokie is the perfect spot for families, groups, or business travelers. With modern finishes and thoughtful touches throughout, you'll find comfort, style, and plenty of room to relax or entertain. Step inside to a bright, open-concept layout featuring multiple cozy seating areas, ideal for gathering and making memories. The kitchen flows effortlessly into the living and dining areas, creating a great space for meals and conversation.

4.97 out of 5 average rating, 500 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.

4.98 out of 5 average rating, 256 reviews

Guest suite in Evanston

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 private guest suite w/kitchenette, 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!

5 out of 5 average rating, 16 reviews

Unique and Historic Lustron Home

Take a trip back to the 50s! This is a fascinating 2 Bedroom Lustron Home built in 1949 is decorated with midcentury modern flair. You will marvel at this home's 100% steel materials and construction including walls, ceilings, cabinets, pocket doors, interior and exterior. The pictures are hung with magnets! You will love the comfort and coziness along with the atomic age style and flair. The yard has both a badminton and croquet sets. There is also an outside patio dining area. Enjoy!

4.87 out of 5 average rating, 151 reviews

Home in Evanston

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

4.96 out of 5 average rating, 138 reviews

Cozy Neighborhood Escape | Near NU-Chicago-Beaches

This is a beautiful, newly renovated apartment that is cozy and contemporary! This unit is located in Evanston’s arts district, surrounded by local shops, tree lined streets, and is a short distance to restaurants, the lakefront, and Northwestern University. Evanston is a suburb just north of Chicago with easy access to the city either by car or public transit. This apartment sleeps up to 4 people and is a 1 bedroom, 1 bath with a sofa sleeper. Don’t miss out. Book Now!

4.91 out of 5 average rating, 108 reviews

Condo in Skokie

Parking Terrace Near Universities Up to 20%OFF

LUXURIES 2 BEDROOMS, 1 BATH APARTMENT WITH LARGE FURNISHED BALCONY. FREE PARKING NEXT TO THE ENTRANCE. BRIGHT & SUNNY SOUTHWESTERN EXPOSURE. LOCATED ON THE FIRST FLOOR-FEW STEPS UP. QUIET PROPERTY IN RESIDENTIAL AREA. MODERN KITCHEN WITH NEW APPLIANCES. KEURIG COFFEE MAKER. CENTRAL AIR & HEATING, HARDWOOD FLOORS, FAST WI-FI INTERNET, LARGE 55" ROKU TV, FREE LAUNDRY. SPARKLING CLEAN APARTMENT. BOOK IT WITH CONFIDENCE YOU WILL ENJOY STAYING HERE, I PROMISE YOU.

4.97 out of 5 average rating, 191 reviews

Stunning, Sunny Flat with Beautiful Backyard

Home away from home in a wonderful and walkable Evanston neighborhood, convenient to downtown, Lake Michigan, Northwestern and more. Treat yourself and your family to this wonderful two-bedroom, masterfully remodeled flat, with all the conveniences and comfort. Off street private parking. Recent updates: New king size bed, 65-inch HD TV, washer & dryer, and more. We follow EPA/CDC protocol and prepare for your stay with intensive cleaning and disinfecting.

4.86 out of 5 average rating, 96 reviews

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

20 mins from popping downtown Chicago and tucked within one of the Northside’s finest tree-line streets—The Haus of Love: A modern wood burning fireplace, new hardwood floors, and a bright airy space greets you in this newly renovated Kosher inspired design Spacious Eat-In Kitchen w/ double everything. Separate Formal Dining. Wetbar. High End Quartz Countertops 3Bd 3.5Bath Master BD w/Heated Floors, 10-ft ceiling, skylights, and a huge 8-ft tub.

4.94 out of 5 average rating, 173 reviews

Guest suite in Evanston

Near Northwestern | Chicago-Sunny & Serene Airbnb

Spacious & private 1 bedroom /1 bath guest suite, with backyard/patio access. Private entrance and walkway with keypad entry. This suite is attached to a single family home. One comfy bedroom, one bath, kitchenette with amenities, (no stove or kitchen sink) sun room/breakfast bar, laptop friendly workspace with desk, wi-fi, relaxing living area. Full cable package. No pets allowed. The home is not wheelchair or ADA compliant.

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Other great holiday rentals in Skokie

4.87 out of 5 average rating, 85 reviews

Cozy Home in Skokie

SamarRating, 5 stars4 months ago

Had a great stay at this Airbnb! Check-in was super easy, and Mian was very responsive, which made everything smooth. The location was very convenient, with easy access by car or train to downtown, close to other suburbs, and not too far from the airport. Overall, a great spot, and I’d definitely stay here again!

Superhost

4.81 out of 5 average rating, 26 reviews

Urban Oasis | Kid Friendly | Quiet Street

RaquelRating, 5 stars1 month ago

My friends and I had a great stay at this property. The host was very quick to respond to questions and was very kind and also was flexible with the check-in time which was super helpful as all of us were arriving at different times. The space was large enough and comfortable for all of us and was in a central location to the places we needed and wanted to go. The beds were very comfortable and there was enough silverware, cups, and plates for us all and the dining table was spacious. The property was in a safe and quiet neighborhood and we were able to uber around easily. I highly recommend this property for groups of friends or family, and there was young children friendly areas and gates and a crib if needed. I would for sure stay at their property again or any of their locations as the host was great!

5 out of 5 average rating, 6 reviews

Apartment in Skokie

Skokie Gem - 1BR on Davis St!

BiancaRating, 5 stars2 weeks ago

The host Vin was awesome. Very quick responses and friendly. The place was very clean and as described in the pictures. My stay was very comfortable and I felt right at home. I enjoyed my time and would definitely book again!

5 out of 5 average rating, 29 reviews

"Hope of Evanston" 2BDR/2BTH

RachelRating, 5 stars1 month ago

Great spot - lots of light, easy to navigate, comfortable, plus communicative hosts. We’ll be back!

Superhost

4.94 out of 5 average rating, 104 reviews

Cozy 2 bedroom house/w garage in Skokie

EmanuelRating, 5 stars2 months ago

Great location, clean and most important affordable.

4.92 out of 5 average rating, 76 reviews

Group Visit Ready | Stunning Home w/ Rooftop Deck

AndreaRating, 5 stars3 days ago

Excellent stay for nearby Northwestern graduation - plenty of beds for all (note: tall people will want to stay on first floor, but basement is well-finished), plenty of hot water for morning rush, easy check-out instructions and super-responsive hosts. All in all, a perfect choice for our extended family weekend!