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Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winnetka vacation rentals

Breakfast, lunch and dinner served

1. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (258 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is ￥29,668
￥33,963 total
includes taxes & fees
Sep 28 - Sep 29
The Gem Museum Suites
Terrace/patio

2. Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (57 reviews)
"Great apt, excellent host"
United States
Colleen B.
The price is ￥17,871
￥41,632 total
includes taxes & fees
Sep 23 - Sep 24
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
Interior

3. Stunning & Stylish Downtown Studio - Highland Park

Stunning & Stylish Downtown Studio - Highland Park
Highland Park
8.4 out of 10, Very good, (7 reviews)
"Great location, quiet area, easy walking into town for breakfast etc"
United States
Tom B.
The price is ￥13,031
￥26,799 total
includes taxes & fees
Oct 4 - Oct 5
Stunning & Stylish Downtown Studio - Highland Park
Exterior detail

4. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (288 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveler
The price is ￥10,762
￥12,980 total
includes taxes & fees
Oct 7 - Oct 8
King Bed Non-Smoking
Terrace/patio

5. Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola

Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
South Evanston
10.0 out of 10, Exceptional, (9 reviews)
"It was a great experience! Very nice and clean place. Advertised exactly as seen. Parking was very easy and the location was great. Overall, would definitely stay again!"
United States
Sophia P.
The price is ￥18,150
￥41,953 total
includes taxes & fees
Sep 29 - Sep 30
Sunny Work From Home Apt: Near Northwestern-Chicago-Beaches-Loyola
1 bedroom, iron/ironing board, WiFi (free), bed sheets

6. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (93 reviews)
"The room was clean, comfortable, and well decorated. The location is walkable and safe. The hosts are very kind and accommodating. We would stay there again."
United States
Katie K.
The price is ￥11,169
￥23,351 total
includes taxes & fees
Oct 5 - Oct 6
Cozy studio in Andersonville Chicago
Interior

7. Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge

Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
Downtown Evanston
9.8 out of 10, Exceptional, (39 reviews)
"This is by far the best experience I’ve had with Abnbs! The place was as advertised, the host was very friendly, prompt and accommodating. "
United States
Brian W.
The price is ￥28,382
￥56,255 total
includes taxes & fees
Oct 7 - Oct 8
Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
Interior

8. Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort

Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
Downtown Evanston
10.0 out of 10, Exceptional, (36 reviews)
"Very nice place to stay with a great location. Thanks!"
United States
Robin M.
The price is ￥31,621
￥65,147 total
includes taxes & fees
Oct 7 - Oct 8
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
Exterior detail

9. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (87 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is ￥17,908
￥33,692 total
includes taxes & fees
Sep 20 - Sep 21
Master qtr close to nature & easy urban facilities
1 bedroom, iron/ironing board, WiFi (free), bed sheets

10. Chic Studio - In Downtown Highland Park, by Metra

Chic Studio - In Downtown Highland Park, by Metra
Highland Park
8.4 out of 10, Very good, (16 reviews)
"I enjoyed my stay at this property. It is in a great location, very unique and super clean! The host is really kind and helpful. "
United States
Deborah
The price is ￥13,728
￥25,829 total
includes taxes & fees
Oct 4 - Oct 5
Chic Studio - In Downtown Highland Park, by Metra
Interior

11. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
The price is ￥10,425
￥47,147 total
includes taxes & fees
Sep 22 - Sep 23
Sleeps 7 • Huge Projector • Designated Workspace
Room

12. 1BR Pad with Homey Feel

1BR Pad with Homey Feel
Lincoln Square
The price is ￥10,083
￥35,597 total
includes taxes & fees
Sep 29 - Sep 30
1BR Pad with Homey Feel
Exterior

13. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,322 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
The price is ￥28,877
￥38,452 total
includes taxes & fees
Sep 27 - Sep 28
Sentral Michigan Avenue
Dining

14. Haus Of Hues: MDRN Bright Peaceful Private Apt

Haus Of Hues: MDRN Bright Peaceful Private Apt
South Evanston
9.6 out of 10, Exceptional, (25 reviews)
"This stay was exactly as listed. Very cute apartment and great location!"
United States
Bradie R.
The price is ￥37,066
￥74,200 total
includes taxes & fees
Sep 22 - Sep 23
Haus Of Hues: MDRN Bright Peaceful Private Apt
TV

15. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
Irving Park
10.0 out of 10, Exceptional, (5 reviews)
"The apartment was just as described, modern, comfortable, very clean and perfect for two people for our five night stay. Very comfortable bed and we especially appreciated the easy entry lock. Great location. Good communication with property manager but we had zero complaints. We would stay again!"
United States
Margaret N.
The price is ￥7,428
￥43,241 total
includes taxes & fees
Sep 22 - Sep 23
Private Workspace • Sleeps4 • Modern Stylish Stay
Interior

16. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (23 reviews)
"Beautiful, unique, and clean place to stay. Comfortable beds, quiet, and plenty of space. Great place to stay."
United States
Richie S.
The price is ￥27,559
￥53,712 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Home by O'Hare + EV Plug
Smart TV, books, printers

17. MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking

MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
South Evanston
9.4 out of 10, Exceptional, (27 reviews)
"Parking was convenient and accommodations were comfortable."
United States
Evan Q.
The price is ￥31,647
￥74,444 total
includes taxes & fees
Sep 29 - Sep 30
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
Lake

18. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (31 reviews)
"Location is perfect to visit Chicago for the weekend. The unit is clean and size is perfect for the family."
United States
Xiaoyu
The price is ￥29,947
￥44,826 total
includes taxes & fees
Sep 20 - Sep 21
Kasa Lake Shore Chicago
Dining

19. "Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
Downtown Evanston
10.0 out of 10, Exceptional, (17 reviews)
"Great spot to stay in Evanston, definitely recommend!"
United States
Surath G.
The price is ￥32,732
￥63,812 total
includes taxes & fees
Sep 29 - Sep 30
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
TV

20. Relaxing 3BR Getaway Close to Dining & Shopping

Relaxing 3BR Getaway Close to Dining & Shopping
Portage Park
9.8 out of 10, Exceptional, (7 reviews)
"Great stay for a family weekend - we were within easy uber distance of our family and downtown - where we went to watch the Chicago marathon."
United States
Surya B.
The price is ￥16,909
￥40,872 total
includes taxes & fees
Sep 21 - Sep 22
Relaxing 3BR Getaway Close to Dining & Shopping
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Stayed for 2 nights, room was great and the staff was friendly. Walking distance to a lot of good restaurants."
Adrian A. 2-night trip
Posted less than an hour ago
Eurostars Magnificent Mile

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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Look no further and take a look at our great range of rental properties in Winnetka!

Frequently asked questions

Can I find vacation rentals in Winnetka?

Yes, we offer vacation rentals near the most popular attractions in Winnetka, or you can go with a more remote option if you're looking for relaxation. 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: Visitors like this Winnetka vacation home rental. It is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Winnetka?

Lake Michigan and Maple Street Beach are a couple of lovely local spots to get outside and enjoy nature. While in the area, you can also visit popular places like Wrigley Field and Navy Pier.

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.