Holiday rentals in Skokie

4.97 out of 5 average rating, 152 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.

4.92 out of 5 average rating, 75 reviews

Group Visit Ready | Stunning Home w/ Rooftop Deck

Gather with friends or family at this MODERN HOME in a quiet, tree-lined North Shore neighborhood. Just 10 minutes to Northwestern University and Lake Michigan—with EASY ACCESS to downtown Chicago—it’s the PERFECT RETREAT. TWO KING beds, a sunny ROOFTOP DECK, and unique murals set the vibe. The OPEN-CONCEPT living area and classy kitchen are perfect for meals, games, or relaxing. With nearby beaches, parks, shops and local favorites, it’s CHOICE for summer getaways, graduations, or group stays.

4.95 out of 5 average rating, 121 reviews

Cute & comfortable apartment on quiet street

Rest and relax at this peaceful and centrally-located spot. This is a cozy & comfortable upstairs apartment located in a quiet, family-friendly neighborhood surrounded by local parks & tree lined streets. It's a short distance to restaurants, the lakefront, and Northwestern University. There is easy parking and it's an easy drive, or a short walk to public transit, to other local universities, Ryan Field, Welsh Ryan Arena, Downtown Chicago, Wrigley Field, and many museums, and concert venues.

4.97 out of 5 average rating, 74 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, 3 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, 499 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, 15 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, 148 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, 135 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!

4.97 out of 5 average rating, 189 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.

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Popular amenities for Skokie holiday rentals

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Air conditioning

Other great holiday rentals in Skokie

Private room in West Rogers Park

4.96 out of 5 average rating, 190 reviews

Welcoming Evanston Home

JoshuaRating, 5 stars2 weeks ago

Jennifer was a very hospitable host and I had a very pleasant stay. The room was very clean and quiet!

4.99 out of 5 average rating, 196 reviews

Private room in Evanston

Comfortable Private Room in Owner Occupied Home

ChristineRating, 5 stars1 week ago

Checking was easy. Instructions are clear and host is responsive. Stephen is accommodating and kind. The home is on a quiet street and I enjoyed spending time in the garden. Sharing the bathroom was not a issue. Stephen is very quiet and discreet. He is a great conversationalist if you want to chat and discreet if you want to relax.

4.98 out of 5 average rating, 179 reviews

Private room in Evanston

Peaceful Suite with natural light. Shared bath

KaeleeRating, 5 stars1 week ago

Irene and Mike were lovely hosts and super helpful. The room was beautifully decorated, light, airy, and super clean. The bed was extremely comfortable and the location was great— in a peaceful neighborhood but also just a short walk from many nice shops and restaurants. I saw at least 4 rabbits in the yard each day of my stay— it felt like a fairytale! I will definitely stay here again during my next visit to Evanston!!

Superhost

Hotel room in Itasca

4.8 out of 5 average rating, 362 reviews

King Bed at Chicago Northwest + PET Friendly

ShayRating, 5 stars3 weeks ago

I’ve stayed here several times and have always enjoyed myself. Terrific value. Thanks for hosting.

Superhost

Private room in Norwood Park

4.8 out of 5 average rating, 223 reviews

Skyline Room, near Medical Ctr, Upstairs

ThoRating, 5 stars5 months ago

Enjoyed my stay, very clean and comfortable. Very convenient and close to airport, train station, bus stop, etc. The host is amazing and responsive to guest’s needs.

4.91 out of 5 average rating, 11 reviews

Private room in Skokie

Home of Peace

RobertRating, 5 stars2 weeks ago

I greatly enjoyed the stay! T was a great host.

Private room in North Park

4.89 out of 5 average rating, 63 reviews

Private Bedroom in Chicago (North Park)

AudreyRating, 5 stars1 week ago

Basic place just to sleep, super affordable!