Winnetka Vacation Rentals

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Vacation Rentals in Winnetka

Indoor pool
Sentral Michigan Avenue

Aparthotel in Downtown Chicago

4.0 star property
9.2 out of 10, Wonderful, (991)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
$126 nightly
The price is $148
Dec 7 - Dec 8
Total with taxes and fees
Sentral Michigan Avenue
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
$145 nightly
The price is $159
Dec 2 - Dec 3
Total with taxes and fees
Sleek 1BR Apt w/ Laundry
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (2)
"Pretty cool place to stay for a short trip ! Everything was close to where we were which made traveling a lot easier. Apartment is a pretty decent size I would recommend just 2-3 people. You can easily contact the host about anything and they’ll respond within a timely manner. The only down side of this place was the shower cleanliness itself. Overall, cool place not bad at all definitely a quick trip kind of thing!"
United States
Majanique M.
$145 nightly
The price is $159
Dec 1 - Dec 2
Total with taxes and fees
West Loop Living – Bright 1BR
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$145 nightly
The price is $159
Nov 30 - Dec 1
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (10)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
$145 nightly
The price is $159
Nov 30 - Dec 1
Total with taxes and fees
Stylish 1BR in West Loop
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (4)
"Convenient location and clean place"
United States
David S.
$145 nightly
The price is $159
Dec 3 - Dec 4
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home
Interior
Gold Coast Living: Modern Studio Unit

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (4)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
$149 nightly
The price is $166
Nov 26 - Nov 27
Total with taxes and fees
Gold Coast Living: Modern Studio Unit
Fridge, microwave, dishwasher, coffee/tea maker
Modern West Loop Gem-City Views & Prime Location 2

Apartment in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (2)
"Apartment was clean and nice. Nice to have off street parking and the hosts were quick to respond. "
United States
Erik R.
Modern West Loop Gem-City Views & Prime Location 2
Free WiFi, bed sheets
Chicago luxury home suites

Aparthotel in Downtown Chicago

2.0 star property
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
$176 nightly
The price is $207
Nov 26 - Nov 27
Total with taxes and fees
Chicago luxury home suites
Terrace/patio
River North Private Balcony With In and Out Parking

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (3)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
$336 nightly
The price is $369
Dec 4 - Dec 5
Total with taxes and fees
River North Private Balcony With In and Out Parking
Business center
Kasa River North Chicago

Aparthotel in Downtown Chicago

4.0 star property
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
$347 nightly
The price is $407
Dec 2 - Dec 3
Total with taxes and fees
Kasa River North Chicago
Interior
Your Chicago get Away

Apartment in Downtown Chicago

8.4 out of 10, Very Good, (8)
"Clean, fun space and responsive host! Loved the views from our room!"
United States
Tyler C.
$415 nightly
The price is $458
Dec 1 - Dec 2
Total with taxes and fees
Your Chicago get Away
Front of property - evening/night
Level Chicago – Old Town

Aparthotel in Downtown Chicago

4.0 star property
9.0 out of 10, Wonderful, (388)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
$207 nightly
The price is $243
Nov 30 - Dec 1
Total with taxes and fees
Level Chicago – Old Town
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Apartment in Downtown Chicago

9.6 out of 10, Exceptional, (14)
"Had a very nice time in Chicago!"
United States
Valerie S.
$167 nightly
The price is $182
Nov 30 - Dec 1
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
Terrace/patio
River North Private Deck With In and Out Parking

Apartment in Downtown Chicago

10.0 out of 10, Exceptional, (3)
"The property was exactly as advertised; clean, good neighborhood, and the views of the city were great. The private outdoor patio access was fantastic."
United States
Rich G.
$446 nightly
The price is $498
Dec 3 - Dec 4
Total with taxes and fees
River North Private Deck With In and Out Parking
Exterior
A quiet stay while you are away

Vacation Home in Oak Park

9.8 out of 10, Exceptional, (32)
"great stay"
United States
matt R.
A quiet stay while you are away
Interior
Montrose Studio:Your Uptown Base

Apartment in Uptown

9.8 out of 10, Exceptional, (7)
"The property was exactly as pictured. The area was safe, had restaurants and coffee shops within a short walk. "
United States
Jamie
$140 nightly
The price is $155
Dec 1 - Dec 2
Total with taxes and fees
Montrose Studio:Your Uptown Base
TV
Nice 1BR Spot, Unwind & Relax

Apartment in Ravenswood

9.8 out of 10, Exceptional, (20)
"Great stay"
United States
Kayla K.
$145 nightly
The price is $159
Dec 1 - Dec 2
Total with taxes and fees
Nice 1BR Spot, Unwind & Relax
Fridge, oven, stovetop, coffee/tea maker
Sunny Studio in Heart of Ravenswood

Apartment in Uptown

9.4 out of 10, Exceptional, (6)
"It was a great stay if you want to experience a diverse, fun, authentic Chicago neigborhood. We really enjoyed it. "
United States
Amer
$134 nightly
The price is $148
Dec 1 - Dec 2
Total with taxes and fees
Sunny Studio in Heart of Ravenswood
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 1

Apartment in Downtown Chicago

9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
$291 nightly
The price is $316
Dec 7 - Dec 8
Total with taxes and fees
River North Rooftop With In and Out Parking 1
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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Top Winnetka Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"The best hotel in Chicago i love it so much best for everything love riu "
Karam 1-night trip
Posted 4 hours ago
Hotel Riu Plaza Chicago

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, 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 $116 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.

Explore a world of travel with Expedia

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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: Visitors like this Winnetka vacation home rental. It offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

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.