Winnetka Vacation Rentals

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Vacation Rentals in Winnetka

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (695)
"Amazing and clean experience I highly recommend "
The price is CA $182
CA $256 total
includes taxes & fees
Mar 11 - Mar 12
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (447)
"A great stay! I’d definitely come back."
The price is CA $136
CA $160 total
includes taxes & fees
Apr 1 - Apr 2
Sonder South Wabash

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (145)
"⭐️⭐️⭐️⭐️⭐️ Had a fantastic stay at Sonder Chicago West Loop during my business trip! The location was perfect for meetings, and I loved having the extra space. The studio felt more like an apartment—super clean, spacious, and well-appointed with stylish decor. The kitchen was fully stocked and well-maintained, making the stay even more comfortable. The reception area was great for getting work done before check-in, and the luggage room lockers were a huge plus. The app-based entry system was...
The price is CA $180
CA $212 total
includes taxes & fees
Mar 11 - Mar 12
Sonder The Burnham Apartments

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (263)
"Beautiful place very much enjoyed our stay thank you! only recommendation is maybe replace old sheets or bleach them found a few dark patches not sure what it was on the sheets and pillows but the bed was very comfortable "
The price is CA $153
CA $180 total
includes taxes & fees
Apr 1 - Apr 2
Sonder Market Hall

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (290)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is CA $233
CA $306 total
includes taxes & fees
Mar 13 - Mar 14
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (373)
"Very nice "
The price is CA $122
CA $289 total
includes taxes & fees
Mar 11 - Mar 12
Kasa Magnificent Mile Chicago

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (262)
"realy great place and very close to everything"
Kasa South Loop Chicago

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (141)
"Loved it Had to leave early but loved "
The price is CA $155
CA $182 total
includes taxes & fees
Apr 8 - Apr 9
Sonder Jewelers Row

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (128)
"We had an overall wodnerful experience. We were celebrating a milestone birthday and was perfect for a group of 4! The room was beautiful and close to everything!! We will definitely come back. "
The price is CA $169
CA $199 total
includes taxes & fees
Mar 20 - Mar 21
Kasa River North Chicago

The Neighborhood Hotel-Little Italy

3.5 star property
9.8 out of 10, Exceptional, (136)
"This place is amazing. So relaxing and comforting. The host is so accommodating and responsive. Everything was great to the point that I did not even want to leave! I shall be back. "
The Neighborhood Hotel-Little Italy

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very good, (92)
"This is the best Sonder property we've ever stayed at!! The location is perfect for Chicago. We had a few different questions during our stay and we always received immediate and thorough answers by using the chat button in the app. Would definitely stay here again!"
The price is CA $140
CA $165 total
includes taxes & fees
Apr 1 - Apr 2
Sonder The Plymouth

Sonder The Opal

3.5 star property
8.4 out of 10, Very good, (30)
"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 $187
CA $220 total
includes taxes & fees
Mar 24 - Mar 25
Sonder The Opal

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (42)
"I loved how easy it was to find and the instructions to access was easy to follow"
The price is CA $171
CA $201 total
includes taxes & fees
Apr 7 - Apr 8
Sonder Greektown

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is CA $111
CA $202 total
includes taxes & fees
Mar 11 - Mar 12
Wrigleyville Suites

ART! 3 bdrm Private HOME-Sleeps 12-Garage-RoofDeck Skyline view-EVTesla-PETS OK

10.0 out of 10, Exceptional, (1)
"My family and I had a wonderful weekend in Chicago, all thanks to your beautiful home. We comfortably slept four people and enjoyed the ample space. The house is filled with stunning natural light during the day, thanks to the full windows on the second floor and a skylight in the stairwell leading to the third floor. One of the features we loved the most was the parking and the use of the garage. The kitchen was easy to navigate, and we appreciated the selection of coffee available."
ART! 3 bdrm Private HOME-Sleeps 12-Garage-RoofDeck Skyline view-EVTesla-PETS OK

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!

9.2 out of 10, Wonderful, (73)
"Loved this location near Wrigley Stadium. "
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-parking!

NEW LUXURY CONDO WITH PATIO DECK

10.0 out of 10, Exceptional, (156)
"This is the perfect place for you to stay when you’re in Chicago. We have stayed here at least four or five times already the place is immaculate. If you need any help someone is there for you ASAP. "
NEW LUXURY CONDO WITH PATIO DECK

Chic Suite/Mins to L Train /Laundry/Free Parking

9.6 out of 10, Exceptional, (36)
"I texted the host a question and he almost immediately got back to me and talked me through the entire check-in process, and he didn’t hang up until he was sure we were able to get in! This was my first out-of-state trip with my boyfriend, so it was an enormous relief to have such a dedicated host to help us out! Additionally, the interior was tidy and very pleasantly decorated!"
The price is CA $115
CA $269 total
includes taxes & fees
Mar 25 - Mar 26
Chic Suite/Mins to L Train /Laundry/Free Parking

Experience Chicago in Hip Logan Square

9.2 out of 10, Wonderful, (5)
"Very clean townhome with all the necessary amenities. Owner was quickly responsive to all communications. Relatively quiet neighborhood. Next door neighbor had a Halloween party on a Sunday night that lasted until 3am. Wasn’t horribly loud but could hear enough noise that I needed to use my noise canceling headphones to sleep. The other nights were very quiet and peaceful. Would stay there again in the future. "
Experience Chicago in Hip Logan Square

Chic, Cozy home, by Blue Line Train Stop + Free parking

9.4 out of 10, Exceptional, (44)
"Just as described and fit our needs perfectly. Super clean"
Chic, Cozy home, by Blue Line Train Stop + Free parking
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

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3881)
"Birthday celebration for weekend for my daughters. They thoroughly enjoy the weekend. The view is amazing! "
The price is CA $138
CA $162 total
includes taxes & fees
Mar 23 - Mar 24
River Hotel

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (1816)
"Property is clean, staff is nice, cost is affordable, restaurants is really good. Location is central. I will be staying again. "
The price is CA $212
CA $249 total
includes taxes & fees
Mar 21 - Mar 22
L7 Chicago by LOTTE

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8606)
"The property is in a very convenient location for nearby attractions. However, the hotel is apparently haunted and we didn't know until we were already there. Otherwise, it was a nice stay."
The price is CA $162
CA $190 total
includes taxes & fees
Apr 10 - Apr 11
Congress Plaza Hotel
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?

Great 3 bedroom rental unit near Logan Square: Visitors like this Winnetka vacation home rental. It is located on a lake and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. 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?

Lake Michigan and Maple Street 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 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.