Compare Winnetka Cabin Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Hotel Options in Winnetka

    Hilton Chicago/Magnificent Mile Suites

    Hilton Chicago/Magnificent Mile Suites

    198 E Delaware Pl Chicago IL
    $81 nightly
    The price is $95 total per night from Jan 5 to Jan 6
    $95 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    8.8/10 Excellent! (3,467 reviews)
    Silversmith Hotel Chicago Downtown

    Silversmith Hotel Chicago Downtown

    10 S Wabash Ave Chicago IL
    $127 nightly
    The price is $149 total per night from Dec 27 to Dec 28
    $149 total
    Dec 27 - Dec 28
    Total with taxes and fees
    9.2/10 Wonderful! (2,109 reviews)
    Club Quarters Hotel Wacker at Michigan, Chicago

    Club Quarters Hotel Wacker at Michigan, Chicago

    75 E Wacker Dr Chicago IL
    $88 nightly
    The price is $103 total per night from Dec 16 to Dec 17
    $103 total
    Dec 16 - Dec 17
    Total with taxes and fees
    8.6/10 Excellent! (1,966 reviews)

What is the price range for Winnetka cabin rentals?


Cabins in Winnetka cost from just $95 a night to $149 a night for that something truly special. Prices and availability are subject to change. Additional terms may apply.

What types of Winnetka cabin are available?


You might fancy a luxury log cabin retreat for a romantic getaway. Maybe you’re after a family lodge in the woods or a rustic hideaway by the water. With a fantastic selection of unique Winnetka cabins to choose from, your perfect escape is just a click away.


How do I find cheap cabin rentals in Winnetka?


To see the latest deals on Winnetka cabins rentals, enter your travel details and hit search. Arrange your results by price to see the cheapest options first and use the budget filter, map, and ratings to compare cabins. We find prices are often lower during , so this could be the best time to find a cabin bargain.


Why should I choose a Winnetka cabin rental?


Picture a cozy space full of personality, space, and privacy. A cabin booked through Orbitz is a place where you can escape the rat race, unwind, and make plans on your private deck, cocooned by trees, water, or views for days. Cook for yourself, just as you like it, share special moments, and build memories.






What amenities will I find in Winnetka cabins?


Sink into your outdoor hot tub in a secluded cabin rental or let the kids splash around in a cabin resort’s indoor pool. Our amenities filters make it easy to find cabins in Winnetka that deliver those special extras that make all the difference.


How do I find pet-friendly cabins in Winnetka?


Click on our pet-friendly filter for woof-tastic Winnetka cabins rentals, where your pooch can enjoy a vacation, too. Take walks to dog-happy cafés, explore nature together from sunrise to sundown, then snuggle together in front of a cozy log fire or under the twinkling stars on your deck.


Are there any luxury cabin rentals in Winnetka?


To find those luxury cabins with the top-notch touches you’re looking for, use the budget filter, read customer reviews, and dip into the property listings for the details. You can then compare cabins and choose the best cabins for a truly luxurious experience.


How do I find some of the best cabins in Winnetka on Orbitz?


Enter your travel details, hit search, and use the filters to see our best deals on cabins in Winnetka. Easy! From luxury log cabin rentals to affordable weekend cabin getaways, Orbitz finds your dream cabin in just a few clicks. You can unlock Orbucks when you sign up for Orbitz RewardsOpens in a new window, too.


Winnetka Cabin Rentals essential information

Accommodation
Cabin Rentals
Lowest Price
$95
Highest Price
$149
Popular accommodation
Hilton Chicago/Magnificent Mile Suites, Silversmith Hotel Chicago Downtown, Club Quarters Hotel Wacker at Michigan, Chicago