Winnetka Vacation Rentals

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Vacation Rentals in Winnetka

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (543)
"Wonderful place "
The price is CA $206
CA $282 total
includes taxes & fees
Sep 30 - Oct 1
Sentral Michigan Avenue
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (370)
"Great place to stay in the South Loop area. Super nice. Super clean. Super quiet."
The price is CA $266
CA $312 total
includes taxes & fees
Oct 21 - Oct 22
Sonder South Wabash
Sonder Market Hall
3.5 star property
8.8 out of 10, Excellent, (161)
"We were really impressed with the location from the green/ pink line. Shopping was a casual 15-20 minutes walk. 2 pubs across the road. Nice safe environment about the location "
The price is CA $160
CA $188 total
includes taxes & fees
Oct 22 - Oct 23
Sonder Market Hall
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (310)
"Wonderful "
The price is CA $311
CA $503 total
includes taxes & fees
Oct 9 - Oct 10
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (258)
"love the property! very beautiful view!"
The price is CA $301
CA $376 total
includes taxes & fees
Sep 29 - Sep 30
Level Chicago – Old Town
Sonder The Burnham
3.5 star property
8.8 out of 10, Excellent, (105)
"Great appartment. Nice to have the kitchen when you do not want to go eat outside. Super well remodeled and well decorated historical building. "
The price is CA $208
CA $245 total
includes taxes & fees
Sep 29 - Sep 30
Sonder The Burnham
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (160)
"Id like to clean rooms and more comunicate with desk personal"
The price is CA $187
CA $219 total
includes taxes & fees
Oct 2 - Oct 3
Found Chicago powered by Sonder
The Neighborhood Hotel-Little Italy
3.5 star property
9.6 out of 10, Exceptional, (75)
"Thank you for being such an affordable and amazing place to stay. I’ll definitely be staying here in the future!"
The Neighborhood Hotel-Little Italy
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (220)
"Mucho olor a marihuana, y que no limpian las habitaciónes solo si pagas adicional y allí dice que cada 14 días limpian y solo es si pagas debería ser un derecho por estar alojado allí por lo menos una vez a la semana no te dan cambio de sábanas ni toallas "
The price is CA $122
CA $129 total
includes taxes & fees
Sep 24 - Sep 25
WoodSpring Suites Chicago Addison
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (92)
"Great place to stay while visiting our son in Chicago. Apartment was clean, safe and front desk staff was friendly and helpful. Close to transportation and plenty of dining options within walking distance. Only let down was furniture in living room was small and a bit uncomfortable for two. "
The price is CA $304
CA $357 total
includes taxes & fees
Sep 29 - Sep 30
Kasa River North Chicago
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (195)
"This location was in the middle of everything, which made our time there more about US, and.less about travel time. "
Kasa South Loop Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (129)
"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"
The price is CA $239
CA $281 total
includes taxes & fees
Sep 30 - Oct 1
Sonder Jewelers Row
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (75)
"We loved being in the loop, and next to the L. Although we had a car, we never used it. We either walked or used CTA. The 4 beds and 3 baths were great for our family of 6, plus the kitchen and washer/dryer in unit were great. We had one small issue, and Sonder handled it quickly."
The price is CA $352
CA $414 total
includes taxes & fees
Oct 14 - Oct 15
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (114)
"Definitely gently used but was comfortable. Ms. Linnie, the host, is very responsive and accommodating. Was missing hair dryers and flat sheets on beds but did not negatively affect our visit."
Luxury Home Away From Your Home
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (166)
"Had a great stay. Ross was a perfect host and made us felt welcomed. "
Walking distance to restaurants, shops and Lake Michigan,
Lovely 2 Bed. 3 Miles from DT w/ Free Parking
8.8 out of 10, Excellent, (18)
"The property was in good condition. Exactly how we expected it to be. This was a last minute trip & the price was overall good. "
The price is CA $157
CA $452 total
includes taxes & fees
Oct 2 - Oct 3
Lovely 2 Bed. 3 Miles from DT w/ Free Parking
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.6 out of 10, Exceptional, (10)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is CA $127
CA $232 total
includes taxes & fees
Oct 15 - Oct 16
Ground Floor Studios in Chicago by 747 Lofts
Sonder The Opal
3.5 star property
8.4 out of 10, Very good, (19)
"Great location. Good amenities with full kitchen and laundry facilities. "
The price is CA $294
CA $346 total
includes taxes & fees
Oct 16 - Oct 17
Sonder The Opal
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (58)
"Super clean place and local to all the good spots. Great host and very responsive!"
Wrigley/Southport Corridor Garden Oasis +parking!
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (210)
"Well maintained and comfortable property, great central location, easy walk to the riverfront, museums, and downtown activities and restaurants. Fantastic city views from the huge balcony (unit 5107), although there's no furniture out there to sit on."
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
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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 types of properties in Winnetka you may be interested in

Congress Plaza Hotel
3.5 star property
7.8 out of 10, Good, (7867)
"Great stay!"
The price is CA $185
CA $217 total
includes taxes & fees
Oct 1 - Oct 2
Congress Plaza Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (3421)
"Very clean room, shower water pressure was actually amazing, and really helpful after my 21 hour day! Pedro at the front desk was very helpful, super polite, great first impression for this hotel! Would definitely recommend this hotel!"
The price is CA $166
CA $195 total
includes taxes & fees
Sep 29 - Sep 30
River Hotel
Eurostars Magnificent Mile
4.0 star property
8.6 out of 10, Excellent, (2573)
"Check in went smoothly and the staff member was excellent."
The price is CA $271
CA $319 total
includes taxes & fees
Oct 1 - Oct 2
Eurostars Magnificent Mile
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.

Frequently asked questions

Can I find vacation rentals in Winnetka?

Yes, we offer vacation rentals in Winnetka near Home Alone House, or you can go with a more remote option if you'd like a relaxing place to stay. Winnetka is known for its shopping and forests. Make sure you have time to check out the sporting events and restaurants during your trip.

What are some of the best vacation rentals in Winnetka?

Luxury Home Away From Your Home: Visitors like this Winnetka vacation home rental. It is equipped with a barbecue grill, air-conditioning, and cable TV to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Winnetka?

Choose from 3 Expedia vacation rentals in Winnetka for a memorable vacation.

What can I see and do in Winnetka?

Family-friendly attractions include Home Alone House and Chocolate Box, whereas Lake Michigan and Maple Street Beach are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places like Wrigley Field and Naval Base Great Lakes.

What are vacation rentals like in Winnetka?

Vacation rentals are private accommodations you can stay in for a couple days or more in Winnetka. Vacation rentals feature extras such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips.