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Our top choices for Winnetka holiday rentals

1. The Gem Museum Suites
The Gem Museum Suites
2. Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
3. Spacious 2BR Close to it All - Chic Apt in Skokie
Spacious 2BR Close to it All - Chic Apt in Skokie
4. Half a mile from everything in the heart of Evanston, Illinois
Half a mile from everything in the heart of Evanston, Illinois
5. Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
6. King Bed Non-Smoking
King Bed Non-Smoking
7. MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
8. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
9. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
10. Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
11. Cozy studio in Andersonville Chicago
Cozy studio in Andersonville Chicago
12. Spacious 4BR near Northwestern with King Beds + Crib
Spacious 4BR near Northwestern with King Beds + Crib
13. Master qtr close to nature & easy urban facilities
Master qtr close to nature & easy urban facilities
14. Great Area Logan Square Apt Games Pets - Sleeps 5
Great Area Logan Square Apt Games Pets - Sleeps 5
15. "Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
16. Chicago Riverhouse with private fenced in oasis
Chicago Riverhouse with private fenced in oasis
17. Cozy apartment with AC and WiFi in awesome Chicago
Cozy apartment with AC and WiFi in awesome Chicago
18. Wrigleyville Suites
Wrigleyville Suites
19. 1BR/1BA City Comfort
1BR/1BA City Comfort
20. Private Workspace • Sleeps 4 • Modern and Stylish
Private Workspace • Sleeps 4 • Modern and StylishFind holiday rentals that suit your style
Top Winnetka Hotel Reviews

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Find out more about Winnetka
Everything you need to know about Winnetka holiday rentals
Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winnetka holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Winnetka holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Winnetka holiday rentals we have selected for you start as low as £56 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 holiday 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 holiday.
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.




































































