Winnetka Vacations from $581

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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.
Glendale Hotel

Glendale Hotel

2.5 out of 5
Somerset
Save 100% on your flight
Price was $989, price is now $581 per person
$581
per person
Jan 30 - Feb 5
found 22 hours ago
Roundtrip flight included
Dallas (DAL) to Los Angeles (LAX)
8.4/10 Very Good! (3,529 reviews)

SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
South of Wilshire
Save 100% on your flight
Price was $1,584, price is now $797 per person
$797
per person
Dec 18 - Dec 25
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
8.2/10 Very Good! (1,005 reviews)
A little bit hard to find, as it’s tucked away, but a great find! It fit my need perfectly, as I was coming from out of town and its right off Santa Monica Blvd., about .5 miles to where I needed to be - easy walking distance. The hotel is clean, the rooms are perfect (especially for a quick trip for one), I loved the soaps in the bathroom, everything you need at a great price. Thank you, Sir Taj!

Reviewed on Nov 13, 2026

The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
Price was $1,647, price is now $999 per person
$999
per person
Dec 27 - Jan 3
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
8.6/10 Excellent! (911 reviews)
Saw German cockroach in the room

Reviewed on Nov 12, 2026

@ Marbella Lane - Luxurious 3BR Penthouse

@ Marbella Lane - Luxurious 3BR Penthouse

4 out of 5
Waterfront
Price was $4,406, price is now $2,736 per person
$2,736
per person
Feb 4 - Feb 8
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Los Angeles (LAX)
No reviews

@ Marbella Lane - Penthouse w/ City & Ocean Views

@ Marbella Lane - Penthouse w/ City & Ocean Views

4.5 out of 5
Waterfront
Price was $4,406, price is now $2,736 per person
$2,736
per person
Feb 4 - Feb 8
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Los Angeles (LAX)
No reviews

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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
Swan Pedal Boat under the Los Angeles skyline

Swan Boat Rental in Echo Park

$13
per adult
Swan Boat Rental in Echo Park
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
$263 nightly
The price is $306 total per night from Nov 22 to Nov 23
$306 total
Nov 22 - Nov 23
Total with taxes and fees
Loews Hollywood Hotel
Hotel Burbank

Hotel Burbank

3 out of 5
150 E Angeleno Ave Burbank CA
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $145 total per night from Dec 14 to Dec 15
$145 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (6,384 reviews)
"A simple hotel with plenty of character… unfortunately, most of that character comes from its age. 😂 The place could definitely use some maintenance and a serious update. It's a bit outdated, quite noisy, and the windows provide such an authentic outdoor experience that you almost forget you're ..."

Reviewed on Nov 13, 2026

Hotel Burbank
The LINE Hotel LA

The LINE Hotel LA

4 out of 5
3515 Wilshire Blvd Los Angeles CA
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $161 total per night from Nov 24 to Nov 25
$161 total
Nov 24 - Nov 25
Total with taxes and fees
The LINE Hotel LA
See all 7,336 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 $581 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.