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House vacation rentals in Skokie

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Top-rated house rentals in Skokie

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Home in Lake View

4.87 out of 5 average rating, 127 reviews

Soak Up Mid-Century Style in Wrigleyville and Boystown

This is an architecturally significant (3-bedroom 3.5-bathroom) home by noted Las Vegas architect Homer Rissman. We are located in the heart of East Lakeview, just half a block from Lake Michigan and Lincoln Park, and blocks away from Wrigley Field and Boystown. Smart TVs (with Netflix, Hulu, Amazon Prime) are located in the shared main level TV lounge, and also the lower level lounge. Entire home I like in-person check-in but full privacy is offered You will receive a link with detailed instructions within 24 hours of your check-in. If you have a U.S. mobile number, you will also receive a text message FULL DISCLOSURE: If you haven't used a lockbox (or don't know how to), self-check-in isn't for you. Your check-in should be in person. Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. You walk to Treasure Island (half block), Jewel Osco (2 minutes), Whole Foods (4 minutes), Lakeview Athletic Club (4 minutes), XSports Fitness (5 minutes), Walgreens (3 blocks), bars and restaurants aound the corner. Close to multiple buses on Lake Shore Drive. Grab a bus to downtown in 15 minutes You will have to climb one flight of stairs for all bedrooms Street parking is free on the east side of Broadway. The west side requires 383 permits. Please, read the signs.

Home in Wicker Park

4.92 out of 5 average rating, 249 reviews

Cool Quiet Coach House, Private Access + Patio

Retreat to the brick patio of this lovingly renovated home after a long day traversing the neighborhood. The interior is an expression of creativity, greyscale walls, rustic accents, and a varied selection of art and wall hangings tie in the decor. Split Level Floor plan. 1st floor = Living, Eat in Kitchen, bedroom 1 and bathroom. 2nd Floor = 2nd bedroom , bath and an additional sleeping area and desk area. Also features a gorgeous shared yard. The entire coach house is yours!! The coach house is set back behind a 2 unit building and the yard is shared between both. We are available via text or airbnb messaging and try to respond quickly. Please reach out anytime if you need anything at all. Extra supplies, neighborhood recommendations or tips in the neighborhood. The home is located on the border of Wicker Park and Bucktown which is Chicago's original hub of cool. It is a vibrant enclave of culture and commerce, explore vintage finds, record stores, and plenty of indie shopping in this trendy part of town The 24 hour Blue Line EL train is just a 5 minute walk. Door to Door it's only 25 minutes to Millennium park. (5 min walk to the blue line, 10 min ride on the train, 10 minute walk to the Park). The neighborhood is pedestrian and bike friendly , the 606 trail is just a few blocks away also.

Home in Naperville

4.93 out of 5 average rating, 104 reviews

California King Bed | Fast Wi-Fi | 75" Smart TV

Our 3bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful, quiet neighborhood. Built w/ cathedral ceilings, there is plenty of space for 10 people to sleep comfortably (6 beds & several comfy couches), as well as 3 smart TVs (w/ complimentary Hulu & Disney+), an indoor fireplace, a gas grill & large yard (including outdoor games), a desk space, & more. Enjoy close access to main roads & large stores (Costco, Walmart, hardware stores, etc.)!

Home in Glen Ellyn

4.85 out of 5 average rating, 102 reviews

Book Now & Build Great Memories in Cozy Cape Cod!

Fall in love w/ this beautiful 3 level Cape Cod home! This amazing 4 bedrooms, 2 bath home offers a modern kitchen w/ stainless steel appliances& granite countertops w/ pantry stocked w/ amenities. Open living room/dining room combo offers natural sunlight and beautiful french doors that lead into a cozy 3 season porch room with lots of windows. The main level has 2 bedrooms, full bath, & hardwood floors. The 2nd level has 2 bedrooms, full bath & lower level has rec room w/ games for family fun!

Home in Irving Park

4.87 out of 5 average rating, 107 reviews

Stunning 6 BR Home * Chicago * Centrally Located

Welcome to a newly built luxury 6 bedroom house in Chicago’s family friendly Albany park neighborhood. Centrally located - close to downtown (25 min), Wrigley Field (15 min) and O'Hare (15 min) Large common areas and a chefs kitchen with a 5 person island allows large parties and families to stay comfortably. The house offers spacious rooms and a full laundry room on the second level. The home also includes a 2 car garage and the convenience of not having to worry about parking in Chicago!

Home in Elgin

4.94 out of 5 average rating, 137 reviews

My Lagoon - 3 br Entire SF home Sleeps 8. King Bed

Welcome to your lagoon. An entire single family house boasting 3 bedrooms with a King bed, 2 queens and a Sofa bed. A true home away from home freshly renovated with tasteful modern coziness. 2 car garage w/ plenty of driveway space for 4 more. You are 25 mins from O'Hare Airport, 35 from the Epic Chicago Dwntwn. Stay Local? Plenty to do ! 10 mins to Now arena, 10 mins to Woodfield Mall, mins away is Villa Olivia, Arboretum, Main Event and more. Short Term, Keyless entry make yourself at home.

Home in Wrigleyville

4.91 out of 5 average rating, 172 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, IMMACULATE SPACIOUS with cozy FIREPLACE + ROOFTOP overlooking skyline! Open 2-story layout w/7 bed options, 3 bathrooms, private rooftop with skyline. Luxury flooring, soaring high ceilings, fully-stocked kitchen + huge island, keyless entry, 2 HD TVs, & outdoor grill. Perfect for SPECIAL OCCASIONS! Next to all Wrigley bars & restaurants. Train to Downtown <12 mins. Private parking for rent. As a "GUEST FAVORITE" we boast >1220 5-star reviews across listings!

Home in Highland Park

4.91 out of 5 average rating, 140 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Experience luxury of this award winning 6BR 4Bath family home in picturesque Northshore private estate. Spend day by the private heated pool, enjoy beauty of gardens, explore local landmarks, starting with the gates of neighborhood Michael Jordan estate. The stylish design and rich amenity list will leave you in awe. ✔ Two-Acre Estate ✔ 6 Comfy BRs ✔ Multiple Living Areas ✔ Full Kitchen ✔ Backyard (Pool, Lounges, BBQ) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

Home in Elmhurst

4.96 out of 5 average rating, 104 reviews

Elmhurst NEW - Super Clean Modern Farmhouse!

Not your average Air BNB!!! 🏡 Newly renovated - CLEAN modern farmhouse in a great location! ✨ ✅Pet Friendly! 🐕 ✅15 min from O'hare. ✈ ✅25 min to Downtown Chicago 🏦 ✅Close to Grocery, restaurants, coffee, shopping, golf, expressways, down town Elmhurst ,Train and Oakbrook and Fashion Outlet Mall. ✅3 great sized bedrooms, 2 living area sofas converts into sleepers ✅Smart TV in family room and Master. ✅ Back patio with dining and seating ✅Large fenced in yard.

Home in Lincoln Park

4.84 out of 5 average rating, 158 reviews

Historic Old Town, Fabulous 4 Bedroom Home

Lovely Historic 4 Bedroom, 3 bathroom home in Old Town, walking distance of restaurants, boutiques, coffee shops, the lake front and excellent public transportation. 2nd Fl. Master Bedroom has a King size bed and Twin plus private bath with bathtub, walk in shower, w/d; 2nd Fl. two room "suite" with a Queen size bed in each room and private bathroom. 1st Fl. bedroom with Queen bed and private bathroom. Off Street Parking and Private Deck!

Home in Naperville

4.88 out of 5 average rating, 124 reviews

Home away from home

Perfect location, walk/bike to downtown area/ High Speed Wifi throughout the house / 2 King size beds one Queen bed /Newly remodeled / Huge back yard / Brand new appliances / Space for your car in a garage or plenty of parking on long driveway/ Outside porch with seating / Pet friendly - no deposit or any other charge. This is my first house ever listed I will add to the describtion more, after people will notice more things, too many to list.

Home in Lake View

4.94 out of 5 average rating, 179 reviews

Wrigleyville Greystone

First floor guesthouse ideal for 6+guests 1 block from Southport brown line station, 1/2 mile from Wrigley Field & red line station. Open floor plan with full kitchen, DR, double LR with 55” TV & foosball table, 3 bedrooms with queen size beds, 2 full bathrooms with bidet toilet, exercise room & back patio with sofas, table & koi pond. Since we live here and have another guests house in the building, we do not allow parties or large groups.

Vacation rentals for every style

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Spaces that are more than just a place to sleep

Popular amenities for Skokie house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Glen Ellyn

4.94 out of 5 average rating, 18 reviews

Glen Ellyn Home

Home in Near South Side

4.86 out of 5 average rating, 29 reviews

2Bed+2Bath PentHouse in South Loop

Home in Bloomingdale

4.94 out of 5 average rating, 35 reviews

Whole House with a Hot Tub!

Home in Bensenville

5 out of 5 average rating, 16 reviews

New! Arcade+Sauna+Slots+Karaoke+more by O’Hare

Home in Schaumburg

4.82 out of 5 average rating, 11 reviews

Schaumburg Oasis with a Pool and Hidden Garden

Home in Lake Forest

4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

Home in Forest Glen

New place to stay

City Close, Country Calm

Home in Carol Stream

4.86 out of 5 average rating, 7 reviews

Spacious 4 Bed/3.5 Bath Sleeps 8+

Weekly house rentals

Home in Wicker Park

4.93 out of 5 average rating, 352 reviews

Amazing Penthouse Skyline Views!

Home in Bridgeport

4.95 out of 5 average rating, 110 reviews

Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

Home in Roscoe Village

4.94 out of 5 average rating, 254 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

Home in Glen Ellyn

4.92 out of 5 average rating, 128 reviews

Home in Glen Ellyn

Home in Bolingbrook

4.92 out of 5 average rating, 119 reviews

The Sunshine Spot

Home in Avondale

4.86 out of 5 average rating, 220 reviews

The Avondale Guesthouse

Home in Chicago Ridge

4.93 out of 5 average rating, 101 reviews

Quiet cul-de-sac with huge fenced in backyard

Home in Logan Square

4.91 out of 5 average rating, 140 reviews

Southwestern Luxury El Motel Dos | Sleeps 12

Private house rentals

Home in Lincoln Park

4.94 out of 5 average rating, 122 reviews

Wrigley Retreat - Full Home w/ Chicago Charm

Home in Lake Zurich

4.77 out of 5 average rating, 35 reviews

Comfortable 4 bedroom home with indoor fireplace

Home in Irving Park

4.9 out of 5 average rating, 48 reviews

3BD/2BA Chicago Avondale/Logan Square House

Home in Schaumburg

4.92 out of 5 average rating, 52 reviews

Eclectic Ranch Home with Large Private Fenced Yard

Home in West Chicago

4.93 out of 5 average rating, 68 reviews

6 Bedrm/3 Bath Retreat/Reunion, Hot Tub, Fireplace

Home in Logan Square

4.95 out of 5 average rating, 39 reviews

Gorgeous and Luxurious 3 BR Home

Home in Chicago

4.84 out of 5 average rating, 103 reviews

Peaceful Family Home near Downtown, MDW, Free Park

Home in Westmont

4.93 out of 5 average rating, 30 reviews

Westmont,Il 4/3 on the Lake

Quick stats about house rentals in Skokie

Total rentals
70 properties
Total number of reviews
2.6K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi

Destinations to explore