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Compare 689 Vacation Homes in Skokie with updated reviews, rates, and availability.

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (27)
"We were pleased with our stay. It met our needs. The only issue we had was the hot water in the bathtub/shower. It didn’t get hot, just tepid. The host had it checked out and said it was working. But we never got a hot shower. Parking was also an issue, but that’s the norm in Chicago. "
Great 3 bedroom rental unit near Logan Square

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

10.0 out of 10, Exceptional, (163)
"Great location, lots of space for gathering and hanging out. Tons of sleeping areas, air mattresses couches, futons, etc. Great for large groups of adults. Caution: Lots of stairs."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

9.6 out of 10, Exceptional, (16)
"Perfect location to make training visits to the area. Close to places to eat & grocery stores."
Single Family home in Schaumburg, IL 3 bed/ 2 full baths/ fully fenced backyard

Updated Forest Park 3 BR Bungalow

10.0 out of 10, Exceptional, (100)
"The home is warm and inviting just like the pictures. Parking in the back of the house was easy. We cooked several times, pans, spices and dishes are available. The neighborhood is only about 20 minutes from downtown Chicago. The fenced in yard was perfect for our dog. We enjoyed our stay "
Updated Forest Park 3 BR Bungalow

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (5)
"We stayed on Valentine's weekend. Used the fireplace and the hot tub as these were must haves for us. Everything was very clean, so I felt a little bad dirtying the fireplace up. The owner was super responsive and accommodating. Would definitely consider staying again if we find ourselves in that area again."
Cozy 3-bedroom house in family-oriented Melrose Park.

LUXE 3 BR, 2 BA + Hot Tub

9.2 out of 10, Wonderful, (22)
"Hot tub was nice, the house itself was clean and had a great backyard that is big and pretty. Host is very responsive. Recommend!!"
The price is SAR 844
SAR 1,481 total
includes taxes & fees
23 Mar - 24 Mar
LUXE 3 BR, 2 BA + Hot Tub

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (87)
"Spacious property. Plenty of room and great neighborhood. Wish the larger TV was upstairs. "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Beautiful 5 bedroom home on private lake

Beautiful 5 bedroom home on private lake

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

9.6 out of 10, Exceptional, (8)
"The house is located in a neighborhood that is easily walkable and has anything you need within walking distance. Metro is located within a few blocks of the house and makes getting around easy."
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Charming ModernRetro Home!

9.2 out of 10, Wonderful, (13)
"Brittany was absolutely amazing. Her home was gorgeous and cozy. Served our needs exact. We will be coming back! "
Charming ModernRetro Home!

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.4 out of 10, Exceptional, (10)
"House was clean and the check in process was easy. The gated driveway easily fit 3 cars with room to spare."
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Riverfront Libertyville Retreat w/ Outdoor Kitchen

9.0 out of 10, Wonderful, (22)
"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."
Riverfront Libertyville Retreat w/ Outdoor Kitchen

The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!

9.8 out of 10, Exceptional, (73)
"We spent a wonderful long weekend enjoying the surrounding area. Plenty of shops, bars and restaurants within easy walking distance. The host was very good with communicating, unit was very spacious and clean. Perfect place to stay in Wrigleyville"
The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!

Chic and Spacious Bi-level 3BD in Bucktown!

2.0 star property
Chic and Spacious Bi-level 3BD in Bucktown!

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (4)
"Delightful home in charming neighborhood. The host was great to deal with, making sure we had what we needed for our toddler. All we had to bring was ourselves!"
Gorgeous historic mansion on UChicago campus. Renovation with original detail.

Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking

9.8 out of 10, Exceptional, (10)
"This was such a nice place in a great location. Really clean, comfortable, everything we needed. I would stay here again. Thank you!"
Luxury duplex home in Roscoe Village/Wrigley Field with Free Steet Parking

New Your Home Away From Home! - Near Great Lakes Naval Base!!

9.2 out of 10, Wonderful, (23)
"Is about 2 miles from great lakes for graduation. Layout is different. Sleeps 11 seats 5 or 6 in the living room, big table...half bath in kitchen...is cold in the winter...have to park in the back...walk around to front.can parknon the street but not overnight. The main bathroom with tyb sbower is high but has handrail. It snowed while we were there...owner shoveled sidewalk once. Overall it suit our need..its not high end but it was nice. Plenty of towels...no wash clothes...clean.."
New Your Home Away From Home! - Near Great Lakes Naval Base!!

The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence

9.6 out of 10, Exceptional, (162)
"we enjoyed our stay"
The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

9.0 out of 10, Wonderful, (7)
"To say we enjoyed our stay, is an understatement. My sister was able you bring in her 21st birthday properly along with her close friends. It was so spacious, everyone had their own area to hang out. The master bedroom is gorgeous, a real selling point. My only regret is that it is winter && we were unable to enjoy the backyard. Our host was amazing and very helpful during the whole process, any question was promptly answered. If you’re looking for a nice place in a quiet area, don’t hesitate to...
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Skokie

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (701)
"Friendly staff "
The price is SAR 507
SAR 705 total
includes taxes & fees
23 Mar - 24 Mar
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (451)
"Overall, really enjoyed the hotel and it had everything we needed. Walls were a little scuffed and could have used some touch ups. But it was very clean and close to the subway"
The price is SAR 350
SAR 411 total
includes taxes & fees
20 Apr - 21 Apr
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (266)
"Appartement spacieux, super fonctionnel, lit et divan lit très confortables. Très bien situé, à 2 min du metro dans un quartier hyper sécuritaire."
The price is SAR 400
SAR 470 total
includes taxes & fees
17 Apr - 18 Apr
Sonder Market Hall
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.