Winnetka Vacation Rentals

Vacation Rentals in Winnetka

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, 425 reviews
"Property was beautiful and well kept. Room was comfortable and felt like home. The pool was disappointing and much smaller than it appears. Communication during check in and valets could be better. "
The price is $199
$263 total
includes taxes & fees
Jul 1 - Jul 2
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very Good, 94 reviews
"It was perfect for my needs for the week! Great area, right across the street from a park! Within walking distance/delivery distance to several dining options! Walking distance to Rush (about 20 minutes) & had 2 bike stations within a 10 minute walk in 2 different directions! Downside was it was near a train station so it was loud when you were outside but I could barely hear it when in the apartment. Plus there was construction going on so that added to the noise. Everything in the apartment...
The price is $97
$114 total
includes taxes & fees
Jun 30 - Jul 1
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, 309 reviews
"Sonder rocks!"
The price is $199
$234 total
includes taxes & fees
Jun 28 - Jun 29
Sonder South Wabash
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Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, 249 reviews
"Parking should be available at a discounted rate. Not free, but in and out privileges at the least would stay agin, if I did not need to travel all over Chicago"
Kasa Magnificent Mile Chicago
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, 131 reviews
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is $189
$222 total
includes taxes & fees
Jun 30 - Jul 1
Found Chicago powered by Sonder
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, 211 reviews
"Loved all the neighborhood dogs & farmers market"
The price is $281
$347 total
includes taxes & fees
Jun 16 - Jun 17
Level Chicago – Old Town
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, 76 reviews
"Very close to Kent Law school. "
The price is $234
$275 total
includes taxes & fees
Jun 30 - Jul 1
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, 34 reviews
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, 67 reviews
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, 106 reviews
"Loved it "
The price is $223
$262 total
includes taxes & fees
Jun 18 - Jun 19
Sonder Jewelers Row
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, 188 reviews
"Very nice property "
The price is $90
$95 total
includes taxes & fees
Jun 6 - Jun 7
WoodSpring Suites Chicago Addison
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, 162 reviews
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very Good, 68 reviews
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is $218
$256 total
includes taxes & fees
Jul 2 - Jul 3
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, 106 reviews
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, 157 reviews
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, 9 reviews
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is $179
$227 total
includes taxes & fees
Jun 17 - Jun 18
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, 39 reviews
"Well renovated, nice bathroom."
Wrigley/Southport Corridor Garden Oasis +parking!
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, 200 reviews
"Everything was perfect. Doormen so nice & helpful. The condo is warm & welcoming. Very easy to feel at home."
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, 8 reviews
"My friends and I stsyed with Alma for a Girl's Weekend. Our stay was comfortable and Alma was there for everything we needed. She was very accommodating. The listing was the perfect place to come to after a long day of exploring Chicago."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
10.0 out of 10, Exceptional, 22 reviews
"we wanted a place that would comfortably accommodate us and our three adult children and their partners-each in separate rooms. This place fit the bill. The views of downtown Chicago are breath taking and the neighborhood is safe and walkable. Thoroughly enjoyed our stay for a family wedding. Only feedback I would provide is additional seating accommodations would be helpful in the living area."
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
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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.

Other types of properties in Winnetka you may be interested in

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, 6,848 reviews
"Great location, historic feel. Pleasant stay"
The price is $167
$196 total
includes taxes & fees
Jun 16 - Jun 17
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very Good, 2,358 reviews
"I loved everything about this property. It was easy to take public transportation with nearby buses and trains.It was close to everywhere i wanted to be and see. Food was good, everything was spotless and smelled really good in the lobby and the suite. I was very comfortable and will definitely stay again."
The price is $201
$237 total
includes taxes & fees
Jul 2 - Jul 3
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
4.0 star property
8.8 out of 10, Excellent, 2,953 reviews
"Excellent stay for us. The room was clean and comfortable. The staff was exceptional. Very professional and friendly. Couldn't ask for a better experience. Thanks."
The price is $179
$210 total
includes taxes & fees
Jun 30 - Jul 1
River 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.

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Winnetka in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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 has air-conditioning and cable TV to help you feel perfectly comfortable 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?

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.

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