Winnetka Vacation Rentals from $173: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Winnetka?

ENVITAE Hotel, 4BR Luxury Modern Apartments : Visitors like this Winnetka vacation home rental. It is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable 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.

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Our top choices for Winnetka vacation rentals

Sentral Michigan Avenue

Downtown Chicago

Luis E.

$245 nightly

Jun 29 - Jun 30

Total with taxes and fees

Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Downtown Chicago

Seke

$409 nightly

Jun 29 - Jun 30

Total with taxes and fees

Wrigleyville Suites

Lakeview

Luka

$248 nightly

Jun 3 - Jun 4

Total with taxes and fees

The Gem Museum Suites

Downtown Evanston

Anton

$151 nightly

Jun 29 - Jun 30

Total with taxes and fees

Cabin 105 by 747 Lofts

West Town

The Oak Park Loft

Oak Park

Linda

$279 nightly

Jun 22 - Jun 23

Total with taxes and fees

Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Lounge

Historic Oak Park Home

Oak Park

Janette

$299 nightly

Jun 23 - Jun 24

Total with taxes and fees

Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Exterior

Historic Oak Park Residence

Oak Park

Ann-Marie

$327 nightly

Jun 22 - Jun 23

Total with taxes and fees

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Top Winnetka Hotel Reviews

Central Loop Hotel

10/10 Excellent

"Had a good time."

Hotel Felix River North/Magnificent Mile

8/10 Good

"The hotel location and room was nice. I didn’t like that you had to pay $5 per bag for storage if you wanted to check out if the room early. I thought giving the room before noon would be better for them especially since I was coming back before that checkout time. So I just brought my stuff back up to the room Other than that the front desk and cleaning ladies was very nice."

Eurostars Magnificent Mile

8/10 Good

"The hotel was in a great location for access to the Magnificent Mile and not too far from the Art Institute and Navy Pier. Because of that though, it was loud all day and night between the sirens and the honking and blasting music. We stayed through a week so this was not just a weekend thing, it’s just loud. If you’re not a light sleeper though, this is a good option"

The Chicago Hotel Collection Ambassador Gold Coast

6/10 Okay

"The room was very clean and well-maintained; however, it was smaller than expected. One issue was the lack of a ventilation fan in the bathroom, which caused odors to linger in the room after use. Additionally, the bathroom layout may be somewhat challenging for larger guests. When I approached the front desk to request a deodorizer, the staff member appeared inconvenienced by the request, which was disappointing. Housekeeping service was also not available during my stay. On a positive note, the lobby was clean and inviting, the bartenders were friendly and attentive, and the view from the property was excellent. Overall, while there were some areas that could be improved, there were also several aspects of the stay that I enjoyed."

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 $173 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.

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Frequently asked questions

Can I find vacation rentals in Winnetka?

Yes, we offer vacation rentals in Winnetka near Chocolate Box, or you can go with a more remote option if you'd like a relaxing place to stay. 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: Visitors like this Winnetka vacation home rental. It is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable 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 enjoy the outdoors, whereas family-friendly attractions include Chocolate Box. While in the area, you can also visit popular places like Wrigley Field and Naval Base Great Lakes.

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.

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Check prices for these dates

Our top choices for Winnetka vacation rentals

Sentral Michigan Avenue

Level Chicago – Old Town

Wrigleyville Suites

The Gem Museum Suites

Cabin 105 by 747 Lofts

The Oak Park Loft

Historic Oak Park Home

Historic Oak Park Residence

River West, Second Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts

Chicago Third Floor Studio by 747 Lofts

Find vacation rentals that suit your style

Top Winnetka Hotel Reviews

Central Loop Hotel

Hilton Chicago

Hotel Felix River North/Magnificent Mile

Hotel Riu Plaza Chicago

The Chicago Hotel Collection - Magnificent Mile

Eurostars Magnificent Mile

The Chicago Hotel Collection Ambassador Gold Coast

River Hotel

Freehand Chicago

Find out more about Winnetka

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