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Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winnetka vacation rentals

A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

1. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (272 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is AED 656
AED 751 total
includes taxes & fees
29 Oct - 30 Oct
The Gem Museum Suites
A patio area with outdoor seating and solar-powered lights.

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 AED 423
AED 958 total
includes taxes & fees
30 Sep - 1 Oct
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

3. 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 AED 253
AED 305 total
includes taxes & fees
4 Oct - 5 Oct
King Bed Non-Smoking
A hotel room with a bed, two pillows, a nightstand with a lamp, and two abstract paintings on the wall.

4. 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 AED 327
AED 638 total
includes taxes & fees
8 Oct - 9 Oct
Chic Studio - In Downtown Highland Park, by Metra
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

5. "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, (18 reviews)
"Great spot to stay in Evanston, definitely recommend!"
United States
Surath G.
The price is AED 775
AED 1,432 total
includes taxes & fees
6 Oct - 7 Oct
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
A modern bedroom with a bed, a sofa, and a hanging plant.

6. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (99 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 AED 248
AED 533 total
includes taxes & fees
26 Oct - 27 Oct
Cozy studio in Andersonville Chicago
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

7. 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, (37 reviews)
"Very nice place to stay with a great location. Thanks!"
United States
Robin M.
The price is AED 749
AED 1,457 total
includes taxes & fees
29 Sep - 30 Sep
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

8. 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 AED 426
AED 783 total
includes taxes & fees
30 Sep - 1 Oct
Master qtr close to nature & easy urban facilities
A hotel room with a bed, a view of a cityscape, and a window with curtains.

9. Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.4 out of 10, Very good, (10 reviews)
"Great location and great place! "
United States
Ryinne P.
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
A modern kitchen with white cabinets, a microwave, and a stove. There is a yellow armchair with a white pillow next to a large gray and white flower painting on the wall.

10. 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 AED 345
AED 697 total
includes taxes & fees
4 Oct - 5 Oct
Stunning & Stylish Downtown Studio - Highland Park
A rooftop terrace with a brick wall, large windows, and a metal railing.

11. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (59 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is AED 264
AED 959 total
includes taxes & fees
5 Oct - 6 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Lounge by the fire pit

12. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is AED 910
AED 2,706 total
includes taxes & fees
8 Oct - 9 Oct
Theater • Game Room • Gym • Firepit • 4BR Home
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

13. 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 AED 672
AED 1,269 total
includes taxes & fees
4 Oct - 5 Oct
Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

14. 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 AED 520
AED 1,106 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Home by O'Hare + EV Plug
A courtyard with a garden, stone building, and wooden house.

15. Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (108 reviews)
"We really enjoyed the space, and it was perfect for us."
United States
Nate T.
The price is AED 467
AED 1,120 total
includes taxes & fees
29 Sep - 30 Sep
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

16. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.6 out of 10, Exceptional, (7 reviews)
"Great location and easy on street parking. "
United States
Lori A.
The price is AED 247
AED 1,076 total
includes taxes & fees
5 Oct - 6 Oct
Sleeps 7 • Huge Projector • Designated Workspace
A compact kitchen with white cabinets, a black stove, a blue countertop, and a white refrigerator.

17. Cozy apartment with AC and WiFi in awesome Chicago

Cozy apartment with AC and WiFi in awesome Chicago
Rogers Park
7.4 out of 10, Good, (16 reviews)
"Great location near university, the lake and public transportation. Felt safe in this area. Room was as described but could certainly use some updates and maintenance."
United States
Kevin G.
The price is AED 735
AED 1,546 total
includes taxes & fees
29 Sep - 30 Sep
Cozy apartment with AC and WiFi in awesome Chicago
A modern kitchen with white cabinets, a stainless steel stove, and a coffee maker.

18. 1BR Well-Equipped Apartment

1BR Well-Equipped Apartment
Lakeview
8.4 out of 10, Very good, (11 reviews)
"Clean"
United States
Annette
The price is AED 522
AED 1,142 total
includes taxes & fees
29 Oct - 30 Oct
1BR Well-Equipped Apartment
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

19. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (68 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
The price is AED 522
AED 905 total
includes taxes & fees
13 Oct - 14 Oct
Chic Urban Retreat Near Wrigley Field w/Parking
An outdoor patio with brick flooring, a grill, and a table with chairs.

20. 1 King Bed | Non-Smoking, Kitchen

1 King Bed | Non-Smoking, Kitchen
Chicago
9.6 out of 10, Exceptional, (15 reviews)
"Everything nice neat and clean"
United States
Anonymous traveler
The price is AED 298
AED 329 total
includes taxes & fees
18 Oct - 19 Oct
1 King Bed | Non-Smoking, Kitchen
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

L7 Chicago by LOTTE

L7 Chicago by LOTTE

8/10 Good
"Rooms were very spacious. Great proximity to Michigan Ave."
Zarmouhi 3-night trip
Posted less than an hour ago
L7 Chicago by LOTTE

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.