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Winnetka Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (305 reviews)
"The rooms were clean, and the staff was courteous and the Breakfast was excellent."
United States
Ernest
$176 nightly
The price is $201
Nov 11 - Nov 12
Total with taxes and fees
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, (60 reviews)
"Great apt, excellent host"
United States
Colleen B.
$230 nightly
The price is $263
Nov 23 - Nov 24
Total with taxes and fees
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
A bedroom with a bed, a ceiling fan, a radiator, a window with blinds, and a potted plant.

3. Spacious 2BR Close to it All - Chic Apt in Skokie

Spacious 2BR Close to it All - Chic Apt in Skokie
West Dempster
9.0 out of 10, Wonderful, (4 reviews)
"Excellent communication with the host. Easy and secure access to the unit. Well furnished and perfect for my trip. So clean! "
United States
Jean W.
$193 nightly
The price is $211
Nov 16 - Nov 17
Total with taxes and fees
Spacious 2BR Close to it All - Chic Apt in Skokie
A modern living room with a sofa, a coffee table, and a TV stand. A kitchen with a microwave, refrigerator, and bar stools is visible in the background.

4. Half a mile from everything in the heart of Evanston, Illinois

Half a mile from everything in the heart of Evanston, Illinois
Downtown Evanston
10.0 out of 10, Exceptional, (13 reviews)
"Great place overall! The coffee machine on the 3rd floor was great to have. Beds comfortable."
United States
Lisa m.
$359 nightly
The price is $410
Nov 11 - Nov 12
Total with taxes and fees
Half a mile from everything in the heart of Evanston, Illinois
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

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
Downtown Evanston
9.8 out of 10, Exceptional, (41 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.
$311 nightly
The price is $355
Nov 9 - Nov 10
Total with taxes and fees
Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

6. King Bed Non-Smoking

King Bed Non-Smoking
Chicago
10.0 out of 10, Exceptional, (289 reviews)
"Clean room and friendly staff made it a good stay."
United States
Anonymous traveler
$67 nightly
The price is $75
Dec 1 - Dec 2
Total with taxes and fees
King Bed Non-Smoking
A modern living room with a blue sofa, a round dining table, and a white desk.

7. 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, (29 reviews)
"Parking was convenient and accommodations were comfortable."
United States
Evan Q.
$393 nightly
The price is $449
Nov 16 - Nov 17
Total with taxes and fees
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
A rooftop terrace with a brick wall, large windows, and a metal railing.

8. 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, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
$207 nightly
The price is $249
Nov 9 - Nov 10
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A rooftop terrace with a brick wall, large windows, and a metal railing.

9. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
$207 nightly
The price is $249
Nov 9 - Nov 10
Total with taxes and fees
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

10. 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, (40 reviews)
"Very nice place to stay with a great location. Thanks!"
United States
Robin M.
$360 nightly
The price is $411
Nov 10 - Nov 11
Total with taxes and fees
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
A bathroom with a bathtub, toilet, sink, and a mirror.

11. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (110 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
$120 nightly
The price is $148
Dec 3 - Dec 4
Total with taxes and fees
Cozy studio in Andersonville Chicago
A dining area with a wooden table set for four, chairs, a vase with yellow flowers, and a kitchen in the background.

12. Spacious 4BR near Northwestern with King Beds + Crib

Spacious 4BR near Northwestern with King Beds + Crib
Evanston
10.0 out of 10, Exceptional, (6 reviews)
"Spacious home that accommodates all our guests. Very close to Northwestern University so travel was easy! Home was clean and well taken care of. Would definitely recommend to others and would stay agin when I’m in the area."
United States
Melissa C.
$857 nightly
The price is $978
Nov 28 - Nov 29
Total with taxes and fees
Spacious 4BR near Northwestern with King Beds + Crib
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

13. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (90 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
$182 nightly
The price is $193
Nov 10 - Nov 11
Total with taxes and fees
Master qtr close to nature & easy urban facilities
A modern living room with a blue sofa, a patterned rug, and a television.

14. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
$166 nightly
The price is $184
Nov 9 - Nov 10
Total with taxes and fees
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

15. "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.
$356 nightly
The price is $407
Nov 10 - Nov 11
Total with taxes and fees
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

16. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
$502 nightly
The price is $578
Nov 19 - Nov 20
Total with taxes and fees
Chicago Riverhouse with private fenced in oasis
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
7.6 out of 10, Good, (17 reviews)
"Great location and clean room! Host was very responsive and helpful!"
United States
Andrew O.
$242 nightly
The price is $298
Nov 9 - Nov 10
Total with taxes and fees
Cozy apartment with AC and WiFi in awesome Chicago
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

18. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (49 reviews)
"Clean room"
United States
Michael
$149 nightly
The price is $174
Nov 10 - Nov 11
Total with taxes and fees
Wrigleyville Suites
A living room with a flat-screen TV on a wooden cabinet, a dark sofa, a coffee table, a floor lamp, and a potted plant.

19. 1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
8.6 out of 10, Excellent, (13 reviews)
"good place to stay clean and comfortable!"
United States
patricia r.
$142 nightly
The price is $155
Nov 9 - Nov 10
Total with taxes and fees
1BR/1BA City Comfort
A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

20. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. The communication was great. Check-in was flawless. We were able to find free parking close by. The listing is accurate, and the location was perfect for our visit to Chicago. We would definitely stay again. Well-equipped kitchen, in-unit laundry, plug strips and extra bedding all were appreciated."
United States
Karin S.
$265 nightly
The price is $312
Nov 21 - Nov 22
Total with taxes and fees
Private Workspace • Sleeps 4 • Modern and Stylish
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
"I would say the best part was the view from the 20th floor looking right at the Magnificent Mile! The windows from ceiling to floor were awesome! The view at night was amazing! Everything was AMAZING!!"
Charlotte 1-night trip
Posted less than an hour ago
Eurostars Magnificent Mile

Find out more about Winnetka

Everything you need to know about Winnetka vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winnetka vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winnetka vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winnetka in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winnetka rentals

At Expedia, we put the best Winnetka vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.