Family-friendly holiday rentals in Skokie

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Top-rated family-friendly rentals in Skokie

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite

Guest suite in Wood Dale

4.91 out of 5 average rating, 506 reviews

The Deer Suite

This is a one bedroom apartment within the home. NOT FOR PARTY No Smoking , ABSOLUTELY No events, parties, or large gatherings. The apartment has a separate entrance from the home main entrance. The apartment also comes with comcast high speed internet. The living room couch can be turned into a double bed, that sleeps two. Large ,shower towels and shampoo included. The apartment includes washer and dryer.The bedroom sleeps two .It is about 30min drive to Downtown-Chicago and15min to O'hare .

Guest favourite

Apartment in Evanston

4.94 out of 5 average rating, 145 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

Top Guest favourite

Apartment in Evanston

4.97 out of 5 average rating, 504 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.

Top Guest favourite

Guest suite in Evanston

4.98 out of 5 average rating, 259 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 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!

Top Guest favourite

Townhouse in Evanston

5 out of 5 average rating, 104 reviews

The NICEST place in Evanston for Families 1500Main

Fully Furnished 2-story, 2 bedroom attached Duplex with a King bed in the Primary bedroom and a pair of Twin beds in the 2nd bedroom. Couch on main floor is also a sofa bed that sleeps two if needed. Main floor is wide open floor plan. This space has been set up specifically for short-term rentals of 1-2 weeks or months and has previously been used by Guests looking for homes in the Evanston area or having construction done. We cater to Families visiting Northwestern University.

Guest favourite

Apartment in Wilmette

4.9 out of 5 average rating, 268 reviews

Spacious Garden Apartment with Sauna and Fireplace

English garden apartment in historic Wilmette home with a private entrance, sauna, washer/dryer, kitchenette, dining area, recreation room with pool table, vintage pinball machine, and a wood-burning fireplace with gas igniter. Two queen beds, 1 full-size sleeper sofa, and a single mattress are available for large families. Ideal access to Northwestern University for all events. **Please note the apartment is located on the garden level and does NOT include the entire home.**

Top Guest favourite

Condo in Chicago

4.99 out of 5 average rating, 290 reviews

Cozy 3BR on Chicago's North Side & Free Parking

Enjoy this charming 3-bedroom condo with free on-site parking just three blocks from Lake Michigan. Convenient access to public transit, including the express bus to downtown (9 miles), Navy Pier, and Grant Park. The CTA Jarvis station is only three blocks away. Perfect for families, business travelers, and couples, this condo is also close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). A great home base to explore all that Chicago has to offer!

Top Guest favourite

Guest suite in Portage Park

4.95 out of 5 average rating, 166 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

Superhost

Home in Evanston

4.77 out of 5 average rating, 191 reviews

Bright 3 bedroom 2 bath Beach / Ryan field close

Light, bright, and cozy home in central Evanston. 3 full bedrooms & two bathrooms perfect for any family. Close to parks, beach, and in between Northwestern University, and Loyola University. Downtown evanston accessible from both public transit & by car. Beach 15 minute walk, very large deck & yard for the warm weather great patio furniture, fire pit, Bbq . There is an apartment in the basement separate entrance from the house. I live in the house sometimes.

Top Guest favourite

Apartment in Evanston

4.99 out of 5 average rating, 259 reviews

Fully furnished apt in downtown Evanston

Downtown Evanston. Cozy quiet area. 4 Rms. Ideal for a couple, family or business travelers. Accommodates 4 sleepers: one queen size and two twin beds. TV & WiFi, microwave, AC & dishwasher. Free off-street parking. Close walk to Northwestern U, Lake Michigan, several supermarkets & many restaurants. Minutes to Metra, Davis & Dempster CTA stations. About 40 minutes to downtown Chicago on CTA Purple Express & less on Metra. Non-smoking.

Guest favourite

Condo in Evanston

4.77 out of 5 average rating, 645 reviews

Spacious Evanston Unit - Walk to Northwestern U

Welcome to my contemporary and spacious garden level unit located on a tree filled, serene residential block in Evanston. Walking distance to Northwestern University, retail areas, trains, golf, and the lovely beaches of Lake Michigan! A Walgreens and a local brewery restaurant are just a few steps away. Plentiful free street parking and free EV chargers one block away.

Guest favourite

Apartment in Skokie

4.89 out of 5 average rating, 229 reviews

Quiet Cozy Ent.Unit free Parking 12 Min 2 Lake

Newly renovated, 2-bedroom apartment, on 2nd floor. 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, Hair dryer. Coffee maker, toaster, large fridge, and many more appliances!