Winnetka Vacation Rentals : Short-Term Rentals for 2025

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Vacation Rentals in Winnetka

"Sandra and Joy are welcoming and helpful. Great front desk."

CA $228 total

includes taxes & fees

Feb 2 - Feb 3

"Easy to find.Had to drive around a little to find parking, but it worked out fine. Easy access with a code or using the Sonder app.Comfortable bed. Very clean room. We did not have any issues with the night club downstairs, but our room was on the 5th floor. The train goes by right next door, but it was kind of a soothing sound. I would definitely stay here again. "

CA $191 total

includes taxes & fees

Feb 20 - Feb 21

Superior Apartment, 1 Bedroom, Balcony, City View | Living area

"Property was convenient and clean. Overall great experience. Street meter parking could be a headache during parking hours but it’s a city thing. Also the incidental feee is a bit confusing with how it’s returned. "

CA $164 total

includes taxes & fees

Feb 26 - Feb 27

"If you are a walker and just want to explore what Chicago has to offer please book this place. You can store your bags before and after checkin/out and the lobby is so nice and quiet. "

CA $212 total

includes taxes & fees

Jan 31 - Feb 1

"Amazing stay ! Love this property every time I’m in Chicago. "

CA $341 total

includes taxes & fees

Feb 13 - Feb 14

49-inch Smart TV with digital channels, TV, streaming services

"Great property. Quick check in and in great location. Will definitely come back "

"It was a Great option, straight and contactless."

CA $204 total

includes taxes & fees

Feb 26 - Feb 27

50-inch Smart TV with satellite channels

"This property was so clean and safe with so many options to eat parking was easy with the parking app. I cannot wait to stay here again. I was at peace. No one was loud or obnoxious. It was perfect if you’re second-guessing this property don’t it’s so convenient and very easy to check in and out of Little Italy was the best. Thank you for such a great experience. Oh, and the heater above the door as you walk in is amazing as well. Lol"

Free toiletries, hair dryer, towels, soap

"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."

CA $193 total

includes taxes & fees

Feb 10 - Feb 11

42-inch Smart TV with digital channels, TV, streaming services

"Everything was great from the beginning. From the instructions on where to park and enter to how to exit. "

"Our stay was amazing. "

CA $182 total

includes taxes & fees

Feb 4 - Feb 5

"Great apartment, we were given an extra bedroom which we used as a wardrobe. Well equipped, modern and well decorated. Full cooker, fridge freezer, microwave. We were provided with tablets for laundry and dishwasher. Washing up.liquids, towels and toilet roll. Great shower. Loved the location. We enjoy cities and walking. Trains a very short walks (several L stations). Target was a 15 minute walk, great independent coffee shop 2 mins from entrance. We will use Sonder again. "

CA $175 total

includes taxes & fees

Feb 23 - Feb 24

40-inch flat-screen TV with digital channels, TV

"The place was awesome, they had to kick out the people before me, so getting my room was a little bit late "

CA $216 total

includes taxes & fees

Feb 24 - Feb 25

"This stay was super nice. Amazing views and super clean. "

CA $140 total

includes taxes & fees

Jan 31 - Feb 1

"All conditions (like the deposit) should be clear in the description. This is not a hotel or a hotel, it's a private place. All this should be clear at the moment of reservation. The property was good enough but the communication with the host was troublesome. And the price is not that low. I will look for a hotel next time. "

CA $203 total

includes taxes & fees

Jan 31 - Feb 1

"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."

1 bedroom, desk, iron/ironing board, travel crib

"We had a great stay in this Evanston lower level studio apartment while in town for our reunion and Homecoming weekend at Northwestern. The studio is clean, nicely decorated, good amenities, and conveniently located to both the NU campus and downtown Chicago. Having a dedicated parking spot was awesome too, as the off-street parking fills up quickly in the evening. My only recommendation would be replacing the really firm mattress with a softer one, or a memory foam topper. All in all we had...

CA $298 total

includes taxes & fees

Feb 4 - Feb 5

"We had a group of couples coming to Chicago from different locations, and this was the perfect spot for us to be all together, but also have our own rooms and spaces. Everything was easy, and when we had a question on parking when we arrived later in the evening, John was very prompt in responding and helping us right away. "

"Thank you so much for sharing your penthouse! We had a very relaxing time and hope to come back sometime when it is a little warmer and we can explore the area more! It was an amazing location for sure! There were so many nice touches from the ample number of outlets/places to charge, the plentiful kleenex boxes, the kitchen amenities and even a fan. We felt right at home and literally needed nothing. Thank you so much for making this past week exactly what we needed!"

"Location of house is great, communication with owner is great. The house "

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"The staff was AMAZING! The hotel, on the oter hand, is terribly out dated. I expected better accommodations for a hotel that's located on Michigan Ave. There's LOTS of room for improvement with the hotel. "

CA $137 total

includes taxes & fees

Feb 19 - Feb 20

"Liked everything! Especially Perilla restaurant, excellent, in fact it was rated the best new restaurant in Chicago for 2024. Will stay there again."

CA $269 total

includes taxes & fees

Feb 2 - Feb 3

"The property was made getting to many downtown locations very easy. Didn't love the transparent shower wall."

CA $167 total

includes taxes & fees

Feb 5 - Feb 6

Find out more about Winnetka

Everything you need to know about Winnetka vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winnetka vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winnetka vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winnetka vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winnetka. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winnetka vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winnetka vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winnetka rentals

At Expedia, we put the best Winnetka vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winnetka rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winnetka vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winnetka. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Winnetka Vacation Rental Travel Info

Popular accommodation	Winnetka private vacation homes
Known landmarks	Writers Theatre, North Shore Center for the Performing Arts and Kohl Children's Museum
International airports	Chicago, IL (ORD-O'Hare Intl.) and Chicago, IL (MDW-Midway Intl.)

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?

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars: Visitors like this Winnetka vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a private yard and a selection of games.

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.

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Winnetka Vacation Rentals

Check prices for these dates

Vacation Rentals in Winnetka

Sentral Michigan Avenue

Sonder Market Hall

Sonder South Wabash

Sonder The Burnham Apartments

Level Chicago – Old Town

Kasa Magnificent Mile Chicago

Found Chicago powered by Sonder

The Neighborhood Hotel-Little Italy

Sonder Jewelers Row

Kasa South Loop Chicago

Sonder The Opal

Sonder The Plymouth

Sonder Greektown

Kasa River North Chicago

Wrigleyville Suites

Walking distance to restaurants, shops and Lake Michigan,

Bright Garden Studio

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

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

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

Other types of properties in Winnetka you may be interested in

Congress Plaza Hotel

L7 Chicago by LOTTE

citizenM Chicago Downtown

Find out more about Winnetka

Winnetka Vacation Rental Travel Info

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Frequently asked questions