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Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (288 reviews)
"Very charming hotel we really enjoyed having breakfast in the morning and ability to have a bottle of wine with dinner at Knight and our bag was very comfortable and nice having the ability to open the window and have some fresh air all in all very charming"
United States
Kathleen
$229 nightly
The price is $262
Nov 12 - Nov 13
Total with taxes and fees
The Gem Museum Suites
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

2. 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.
$406 nightly
The price is $461
Oct 18 - Oct 19
Total with taxes and fees
Chicago's Hidden Treasure "Evanston, IL" Urban Luxury with comfort
A modern kitchen with granite countertops, a double sink, and pendant lighting.

3. "Faith of Evanston" 180°view, 2BDR +2Bath Urban luxury

"Faith of Evanston" 180°view, 2BDR +2Bath Urban luxury
Downtown Evanston
10.0 out of 10, Exceptional, (23 reviews)
"very clean, easy check in, nice location and comfortable beds. would stay again"
United States
Nicole N.
$523 nightly
The price is $594
Oct 18 - Oct 19
Total with taxes and fees
"Faith of Evanston" 180°view, 2BDR +2Bath Urban luxury
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

4. 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.
$352 nightly
The price is $400
Oct 20 - Oct 21
Total with taxes and fees
Executively Appointed Condo, w/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
A patio area with outdoor seating and solar-powered lights.

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

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (59 reviews)
"Great apt, excellent host"
United States
Colleen B.
$247 nightly
The price is $280
Nov 9 - Nov 10
Total with taxes and fees
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

6. "Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite

"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite
Evanston
9.8 out of 10, Exceptional, (63 reviews)
"Great stay!"
United States
Angela D.
$491 nightly
The price is $558
Oct 25 - Oct 26
Total with taxes and fees
"Serenity of Evanston" 2 BDR/2Bath Modern-Luxe Suite
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.

7. 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.
$169 nightly
The price is $179
Nov 16 - Nov 17
Total with taxes and fees
Stunning & Stylish Downtown Studio - Highland Park
A modern living room with a blue sofa, a round dining table, and a white desk.

8. 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.
$427 nightly
The price is $485
Oct 19 - Oct 20
Total with taxes and fees
MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
A building with a stone facade and a large window displaying the text 'LAUNDRY MAT'.

9. 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
$72 nightly
The price is $82
Oct 18 - Oct 19
Total with taxes and fees
King Bed Non-Smoking
A modern interior with a dining area, seating, a fireplace, and large windows offering a view of buildings outside.

10. "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.
$401 nightly
The price is $455
Oct 19 - Oct 20
Total with taxes and fees
"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym
A modern bedroom with a bed, a sofa, and a hanging plant.

11. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (104 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.
$113 nightly
The price is $139
Nov 2 - Nov 3
Total with taxes and fees
Cozy studio in Andersonville Chicago
A modern kitchen with wooden cabinets, a microwave, a stove, and a coffee maker.

12. The Lincoln Square Hideaway

The Lincoln Square Hideaway
Lincoln Square
10.0 out of 10, Exceptional, (27 reviews)
"Great place! Highly recommended."
United States
Ian
$371 nightly
The price is $457
Oct 19 - Oct 20
Total with taxes and fees
The Lincoln Square Hideaway
A hotel room with a bed, two pillows, a nightstand with a lamp, and two abstract paintings on the wall.

13. 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
$149 nightly
The price is $158
Nov 8 - Nov 9
Total with taxes and fees
Chic Studio - In Downtown Highland Park, by Metra
A rooftop terrace with a brick wall, large windows, and a metal railing.

14. 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.
$291 nightly
The price is $351
Oct 21 - Oct 22
Total with taxes and fees
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A modern building with the name 'SENIORAL' prominently displayed on the facade.

15. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,374 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
$143 nightly
The price is $168
Nov 9 - Nov 10
Total with taxes and fees
Sentral Michigan Avenue
A pedestrian bridge with metal railings and a staircase leading up to a building.

16. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (71 reviews)
"The app isn’t letting me give 5 stars but I would give 5 stars for all categories. It was perfect for our needs. Two adults and two kids. Perfect location and easy to get in and out with our car off the street. Beds were comfy and the main rooms were spacious. They were super responsive for our last minute booking. Would definitely stay here again!"
United States
Bridget
$205 nightly
The price is $211
Nov 2 - Nov 3
Total with taxes and fees
Chic Urban Retreat Near Wrigley Field w/Parking
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

17. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (88 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
$196 nightly
The price is $208
Oct 27 - Oct 28
Total with taxes and fees
Master qtr close to nature & easy urban facilities
A hotel room with a bed, a view of a cityscape, and a window with curtains.

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

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.6 out of 10, Excellent, (11 reviews)
"Great location and great place! "
United States
Ryinne P.
$339 nightly
The price is $348
Oct 20 - Oct 21
Total with taxes and fees
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
A modern kitchen with a large island, bar stools, and a city view.

19. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (541 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
$279 nightly
The price is $327
Nov 1 - Nov 2
Total with taxes and fees
Level Chicago – Old Town
A compact kitchen with white cabinets, a black stove, a blue countertop, and a white refrigerator.

20. 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 and clean room! Host was very responsive and helpful!"
United States
Andrew O.
$341 nightly
The price is $421
Oct 20 - Oct 21
Total with taxes and fees
Cozy apartment with AC and WiFi in awesome Chicago
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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Room smelled so clean and fresh! Our room size was perfect for our stay. Staff was super nice and helped a lot. I did wish a microwave was available in the room. Location was great - nearby stores, cafes and a good bagel spot. Neighborhood was safe and secure. Would recommend the hotel for future stays."
Kanae 2-night trip
Posted 3 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

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 $82 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.