Winnetka Vacation Rentals

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Vacation Rentals in Winnetka

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (629)
"The view was excellent "
The price is CA $157
CA $227 total
includes taxes & fees
Dec 29 - Dec 30
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (343)
"Great stay "
Kasa Magnificent Mile Chicago

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (407)
"Outstanding accommodations! Will choose this property again for my travels."
The price is CA $178
CA $209 total
includes taxes & fees
Jan 15 - Jan 16, 2025
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (228)
"Very nice place for the cost. Could hear outside and inside noises but noise doesn’t bother me. Would stay here again."
The price is CA $91
CA $106 total
includes taxes & fees
Jan 21 - Jan 22, 2025
Sonder Market Hall

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (277)
"I loved the amenities available to us - garage parking, washer/dryer in unit, full kitchen and fully furnished. Staff were polite and helpful. Great location"
The price is CA $254
CA $326 total
includes taxes & fees
Jan 4 - Jan 5, 2025
Level Chicago – Old Town

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (248)
"Everything was great from the beginning. From the instructions on where to park and enter to how to exit. "
Kasa South Loop Chicago

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (110)
"Very clean and walkable area. "
The price is CA $178
CA $210 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Kasa River North Chicago

Sonder The Burnham Apartments

3.5 star property
9.0 out of 10, Wonderful, (122)
"Wonderful place with some personality "
The price is CA $180
CA $212 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Sonder The Burnham Apartments

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (179)
"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...
The price is CA $173
CA $203 total
includes taxes & fees
Jan 19 - Jan 20, 2025
Found Chicago powered by Sonder

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (112)
"The property was exceptionally clean and offered plenty of space."
The Neighborhood Hotel-Little Italy

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (136)
"Sonder check in experience as a first timer was super easy! Great instructions and no issues entering or exiting the property. Property was in great condition with all the amenities you could need. Only downside was the cigar bar downstairs... you could at certain times of day smell the cigar scent in our room upstairs. Not a huge issue, but if you were sensitive to the smell it would not be ideal."
The price is CA $164
CA $192 total
includes taxes & fees
Jan 13 - Jan 14, 2025
Sonder Jewelers Row

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (87)
"Loved the location. "
The price is CA $148
CA $174 total
includes taxes & fees
Jan 23 - Jan 24, 2025
Sonder The Plymouth

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (174)
"We were very pleased with the property. Stayed there over the Thanksgiving holiday & weekend while visiting my older daughter. Nice neighborhood & easy location to get to other parts of the city. Everything was as depicted in the description and communication with management was excellent. Would stay here again."
Walking distance to restaurants, shops and Lake Michigan,

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (28)
"We loved the location in River North with shops around plenty of nice restaurants. Walkable and good buses around. Apartment was very nice, we were 5 adults. A bit noisy because of bar nearby ( it depends of your tolerance to noise. Some of us were disturbed some heard nothing). We enjoyed our stay !"
The price is CA $161
CA $189 total
includes taxes & fees
Jan 16 - Jan 17, 2025
Sonder The Opal

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (36)
"The place was awesome, they had to kick out the people before me, so getting my room was a little bit late "
The price is CA $181
CA $213 total
includes taxes & fees
Jan 14 - Jan 15, 2025
Sonder Greektown

Wrigley/Southport Corridor Garden Oasis +parking!

9.8 out of 10, Exceptional, (68)
"Very clean and comfortable place!"
Wrigley/Southport Corridor Garden Oasis +parking!

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

10.0 out of 10, Exceptional, (215)
"Excited about our trip to Chicago and was not disappointed. Communication was very good from the homeowner location is perfect we had a fantastic time would recommend this for anyone wanting to enjoy downtown Chicago"
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Experience Chicago living near United Center

9.4 out of 10, Exceptional, (12)
"Our family stayed for a corporate training and we had a great experience. The neighborhood wasn't the best but we felt very secure with having a garage to use. Very thankful for the quick communication! from the p "
Experience Chicago living near United Center

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.8 out of 10, Exceptional, (11)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
Ground Floor Studios in Chicago by 747 Lofts
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, (8286)
"The hotel is very historic and beautifully decorated. We had a junior suite that was extremely roomy and very clean. The furniture was nice, but didn’t seem to match the historic charm of the hotel being that the decor in the room was ultra modern. The bathroom was huge, but the tub wasn’t updated and was very small. Overall, it was a nice experience and I’d definitely recommend staying."
The price is CA $150
CA $176 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Congress Plaza Hotel

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3632)
"Amazing location, lots of shopping and great food within a walkable distance (0.3-1mi). Only downside was the bathroom products, the soap they provide makes your skin incredibly dry which is terrible in combination with the cold weather. "
The price is CA $149
CA $175 total
includes taxes & fees
Jan 7 - Jan 8, 2025
River Hotel

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3111)
"Very friend and helpful staff. The onsite restaurants were great. Close to everything. "
The price is CA $212
CA $291 total
includes taxes & fees
Jan 19 - Jan 20, 2025
Hyatt Regency 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.

Frequently asked questions

Can I find vacation rentals in Winnetka?

Yes, we offer vacation rentals in Winnetka near Chocolate Box, 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?

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!: Visitors like this Winnetka vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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?

Lake Michigan and Elder Lane Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Chocolate Box. While in the area, you can also visit popular places like Naval Base Great Lakes and Michigan Avenue.

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.