Winnetka Vacation Rentals

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Vacation Rentals in Winnetka

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (988)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is ¥15,761
¥23,092 total
includes taxes & fees
Dec 8 - Dec 9
Sentral Michigan Avenue

Sleek 1BR Apt w/ Laundry

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
Sleek 1BR Apt w/ Laundry

West Loop Living – Bright 1BR

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.
The price is ¥8,603
¥24,887 total
includes taxes & fees
Dec 1 - Dec 2
West Loop Living – Bright 1BR

1BR Modern Luxe Apt with In-Unit Laundry

Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ¥8,658
¥25,046 total
includes taxes & fees
Dec 2 - Dec 3
1BR Modern Luxe Apt with In-Unit Laundry

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (9)
"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.
The price is ¥8,603
¥24,887 total
includes taxes & fees
Nov 30 - Dec 1
Stylish 1BR in West Loop

The One: A 1BR Stay That Feels Like Home

Downtown Chicago
9.4 out of 10, Exceptional, (3)
"Convenient location and clean place"
United States
David S.
The price is ¥8,603
¥24,887 total
includes taxes & fees
Dec 3 - Dec 4
The One: A 1BR Stay That Feels Like Home

Gold Coast Living: Modern Studio Unit

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"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
The price is ¥10,792
¥25,887 total
includes taxes & fees
Nov 26 - Nov 27
Gold Coast Living: Modern Studio Unit

Modern West Loop Gem-City Views & Prime Location 2

2.0 star property
Downtown Chicago
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.
The price is ¥23,769
¥31,846 total
includes taxes & fees
Dec 1 - Dec 2
Modern West Loop Gem-City Views & Prime Location 2

Chicago luxury home suites

2.0 star property
Downtown Chicago
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
The price is ¥45,750
¥53,707 total
includes taxes & fees
Nov 23 - Nov 24
Chicago luxury home suites

River North Private Balcony With In and Out Parking

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.
River North Private Balcony With In and Out Parking

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago

Your Chicago get Away

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.
The price is ¥34,295
¥69,805 total
includes taxes & fees
Nov 24 - Nov 25
Your Chicago get Away

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (386)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (14)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is ¥9,697
¥28,710 total
includes taxes & fees
Nov 30 - Dec 1
Twice as Nice: Chic 2BR Stay with Style & Space

River North Private Deck With In and Out Parking

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.
The price is ¥37,538
¥77,814 total
includes taxes & fees
Dec 3 - Dec 4
River North Private Deck With In and Out Parking

A quiet stay while you are away

Oak Park
9.8 out of 10, Exceptional, (32)
"great stay"
United States
matt R.
A quiet stay while you are away

Montrose Studio:Your Uptown Base

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
The price is ¥9,385
¥24,238 total
includes taxes & fees
Dec 8 - Dec 9
Montrose Studio:Your Uptown Base

Nice 1BR Spot, Unwind & Relax

Ravenswood
9.8 out of 10, Exceptional, (19)
"Great stay"
United States
Kayla K.
The price is ¥8,603
¥24,887 total
includes taxes & fees
Dec 2 - Dec 3
Nice 1BR Spot, Unwind & Relax

Sunny Studio in Heart of Ravenswood

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
The price is ¥8,446
¥23,139 total
includes taxes & fees
Dec 9 - Dec 10
Sunny Studio in Heart of Ravenswood

River North Rooftop With In and Out Parking 1

Downtown Chicago
9.0 out of 10, Wonderful, (2)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is ¥16,579
¥49,065 total
includes taxes & fees
Dec 22 - Dec 23
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

Find out more about Winnetka

Search for holiday rentals in Winnetka on Expedia! You can easily find your home rentals, villas, holiday apartments in Winnetka using one of the methods below:

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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.