Winnetka Vacations from $255

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Your Winnetka Vacation

Reserve a Winnetka vacation package and concentrate on what matters — having fun. There's no more stressful planning, just a lot more time to savor the best of this interesting city, such as its family-friendly attractions and lively atmosphere. Any trip to Winnetka needs a well-designed itinerary. Fill yours with major attractions like California State University-Northridge, Westfield Topanga and Woodley Park. A few clicks is all it takes to craft a tailor-made Winnetka vacation on Expedia.

The Latest Winnetka vacation packages

Price found within the past 48 hours. Click for updated prices.
The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
Price was $525, price is now $255 per person
$255
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to Los Angeles (LAX)
8.6/10 Excellent! (740 reviews)
This was a great stay. Clean room, quiet and had everything I needed for my time there.

Reviewed on Jul 21, 2026

Encore Inn Inglewood

Encore Inn Inglewood

2.5 out of 5
Lockhaven
Price was $855, price is now $322 per person
$322
per person
Sep 4 - Sep 8
found 2 days ago
Roundtrip flight included
Denver (DEN) to Los Angeles (LAX)
6.4/10 (173 reviews)
Walked in the room and walked out Room had roaches and mice walking around Blanket looked dirty The room had an awful smell The worker offer another room but it was the same The picture on the website showed a nice looking place but once you see it real bad

Reviewed on Jul 13, 2026

SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
South of Wilshire
Price was $1,304, price is now $531 per person
$531
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Los Angeles (LAX)
8.2/10 Very Good! (1,006 reviews)

Dream Inn

Dream Inn

3 out of 5
Lockhaven
Price was $1,374, price is now $581 per person
$581
per person
Sep 4 - Sep 8
found 2 days ago
Roundtrip flight included
Denver (DEN) to Los Angeles (LAX)
7/10 Good! (71 reviews)

Le Bon Hotel Hollywood

Le Bon Hotel Hollywood

2 out of 5
Hollywood
Price was $757, price is now $364 per person
$364
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Los Angeles (LAX)
7.6/10 Good! (431 reviews)
I arrive and am immediately forced to check in with a virtual assistant in India who has zero customer service skills. As he's figuring out how to check me in, I have to stand in a 100 degree waiting room. I immediately asked for a refund and they refused to give it to me. I booked two hours prior and they refused to give me my money back.

Reviewed on Jul 20, 2026

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What to do in Winnetka

Disneyland® Park

Disneyland® Resort Tickets

$166
per adult
88% of travellers recommend
Disneyland® Resort Tickets
Los Angeles: Natural History Museum of LA Entry Ticket

Los Angeles: Natural History Museum of LA Entry Ticket

$18
per adult
96% of travellers recommend
Los Angeles: Natural History Museum of LA Entry Ticket
ae2917ea56584e7da7978b2a97acb30c

City Cruises Marina del Rey: Premier Dinner Cruise

$132
per adult
86% of travellers recommend
City Cruises Marina del Rey: Premier Dinner Cruise
See all activities in Winnetka

Winnetka Hotel Deals

Loews Hollywood Hotel

Loews Hollywood Hotel

4 out of 5
1755 North Highland Avenue Los Angeles CA
Fully refundableReserve now, pay when you stay
$248 nightly
The price is $288 total per night from Jul 29 to Jul 30
$288 total
Jul 29 - Jul 30
Total with taxes and fees
9.2/10 Wonderful! (5,340 reviews)
"It's a good location"

Reviewed on Jul 21, 2026

Loews Hollywood Hotel
Sheraton Universal Hotel

Sheraton Universal Hotel

4 out of 5
333 Universal Hollywood Drive Universal City CA
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $218 total per night from Aug 16 to Aug 17
$218 total
Aug 16 - Aug 17
Total with taxes and fees
8.8/10 Excellent! (4,251 reviews)
"Muy cerca de estudios universales"

Reviewed on Jul 21, 2026

Sheraton Universal Hotel
Hotel Burbank

Hotel Burbank

3 out of 5
150 E Angeleno Ave Burbank CA
Fully refundableReserve now, pay when you stay
$153 nightly
The price is $172 total per night from Aug 16 to Aug 17
$172 total
Aug 16 - Aug 17
Total with taxes and fees
Hotel Burbank
See all 7,504 properties in Winnetka
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.

Find the Best Winnetka Vacation Packages

Winnetka Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Los Angeles Intl. Airport (LAX)
Max Temp Winter
65ºF
Max Temp Summer
80ºF
Top Sights
Getty Center, Topanga State Park and Will Rogers State Beach

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Frequently asked questions

How much does a Winnetka vacation package cost?
You'll find cheap prices from $255 on Expedia for your Winnetka break. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Winnetka costs.
What are the cheapest months to go to Winnetka?
You can generally find lower rates and greater availability in January, June and November. Explore our cheap Winnetka vacation packages and you could get some great off-season deals.
How many days is enough for Winnetka?
Typically, a handful of days is enough to go to the major sights during your Winnetka vacation. However, if you'd like to have more time to unwind or go on day tours, think about extending your itinerary.
How to find the best Winnetka package deals?
Start your search for a Winnetka package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Winnetka package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winnetka getaway off to a flying start.
Is it cheaper to book a Winnetka vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still get the freedom to create a tailored Winnetka vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Winnetka?
If you've got your Winnetka travel dates finalized, book as early as you can to bag some outstanding deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for traveling on a whim.
Does Expedia offer Book Now, Pay Later Winnetka vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Winnetka vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.