Winnetka Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Winnetka vacation rentals

Dining

Relaxing Getaway w/ Game Room, Pickleball & More

Relaxing Getaway w/ Game Room, Pickleball & More
Canoga Park
10.0 out of 10, Exceptional, (5 reviews)
"Nice place, great amenities with the game room. Teens loved it, clean and great home. "
United States
Amberly H.
$568 nightly
The price is $638
May 12 - May 13
Total with taxes and fees
Relaxing Getaway w/ Game Room, Pickleball & More
Marina

Cozy Romantic Sailboat Experience, Safe Marina + Walk to Bars, Dining and more!

Cozy Romantic Sailboat Experience, Safe Marina + Walk to Bars, Dining and more!
Marina del Rey
8.6 out of 10, Excellent, (67 reviews)
"The place was perfect for what I needed!"
United States
Taylor
$148 nightly
The price is $155
May 7 - May 8
Total with taxes and fees
Cozy Romantic Sailboat Experience, Safe Marina + Walk to Bars, Dining and more!
Property grounds

Luxury Covered Wagon in Santa Monica Mountains close to Malibu w/ King Bed

Luxury Covered Wagon in Santa Monica Mountains close to Malibu w/ King Bed
Westlake Village
10.0 out of 10, Exceptional, (9 reviews)
"Our whole family loved staying here. Despite this being a glamping spot, the inside of the wagon and the bathroom were very clean. "
United States
Olga C.
$292 nightly
The price is $292
May 10 - May 11
Total with taxes and fees
Luxury Covered Wagon in Santa Monica Mountains close to Malibu w/ King Bed
TV

HILL SIDE GETAWAY next to Magic Mountain, and close to all theme parks

HILL SIDE GETAWAY next to Magic Mountain, and close to all theme parks
Santa Clarita
10.0 out of 10, Exceptional, (4 reviews)
"Located just where I needed it to be and close to lots of convenience items (Costco and several different grocery stores, as well as a wide variety of cuisines at restaurants nearby) "
United States
Breanna D.
$165 nightly
The price is $165
May 11 - May 12
Total with taxes and fees
HILL SIDE GETAWAY next to Magic Mountain, and close to all theme parks
Interior

Topanga Creative Suite + Private Trails & Creeks

Topanga Creative Suite + Private Trails & Creeks
Topanga
9.4 out of 10, Exceptional, (6 reviews)
"Great ground-level suite with large living/dining area, small bedroom, kitchen, and nice bathroom. Very rural and quiet, especially for L.A. "
United States
Jonathan W.
$145 nightly
The price is $145
May 10 - May 11
Total with taxes and fees
Topanga Creative Suite + Private Trails & Creeks
Fridge, microwave, oven, stovetop

Fabulous guest house just minutes away from anything you would need!

Fabulous guest house just minutes away from anything you would need!
Grandview
9.8 out of 10, Exceptional, (63 reviews)
"The kitchen was fully equipped, the walk in closet had more sheets and blankets than I needed. The bathroom was spotless and well equipped also. The outside area was clean and lively, but it was raining so we didn’t use it. I’d stay there again. "
United States
Mer L.
$207 nightly
The price is $222
May 14 - May 15
Total with taxes and fees
Fabulous guest house just minutes away from anything you would need!
Exterior

Modern Studio House - Fully private & 5 min to beach

Modern Studio House - Fully private & 5 min to beach
Culver - West
10.0 out of 10, Exceptional, (17 reviews)
"We had a great experience with this place"
United States
Marissa F.
$192 nightly
The price is $216
May 7 - May 8
Total with taxes and fees
Modern Studio House - Fully private & 5 min to beach
Interior

Mermaid Suite + Private Trails, Cave and Creek!

Mermaid Suite + Private Trails, Cave and Creek!
Topanga
9.0 out of 10, Wonderful, (12 reviews)
"great place"
United States
Harold
$165 nightly
The price is $165
May 7 - May 8
Total with taxes and fees
Mermaid Suite + Private Trails, Cave and Creek!
Fridge, microwave, oven, stovetop

"The Best" Jacuzzi View Private Luxury Guest Cottage-Better than a Room or Suite

"The Best" Jacuzzi View Private Luxury Guest Cottage-Better than a Room or Suite
Thousand Oaks
9.8 out of 10, Exceptional, (43 reviews)
"Quality cottage, clean, comfortable and well thought out. Helpful host. Would stay again"
United Kingdom
Robert
$358 nightly
The price is $358
May 7 - May 8
Total with taxes and fees
"The Best" Jacuzzi View Private Luxury Guest Cottage-Better than a Room or Suite
Smart TV, printers

Family friendly in the heart of Westlake Village! King beds, workstation,printer

Family friendly in the heart of Westlake Village! King beds, workstation,printer
Westlake Village
9.8 out of 10, Exceptional, (30 reviews)
"We enjoyed our stay during a difficult time. Would stay here again in the future. "
United States
Shannon B.
$307 nightly
The price is $318
May 10 - May 11
Total with taxes and fees
Family friendly in the heart of Westlake Village! King beds, workstation,printer
1 bedroom, free WiFi, bed sheets

Secluded Nature Retreat • Near Hiking • Private Studio Escape LA

Secluded Nature Retreat • Near Hiking • Private Studio Escape LA
Chatsworth
$255 nightly
The price is $255
May 11 - May 12
Total with taxes and fees
Secluded Nature Retreat • Near Hiking • Private Studio Escape LA
Family House, City View | Private kitchen | Full-size fridge, microwave, oven, stovetop

Casa Sycamore by Oraklus

Casa Sycamore by Oraklus
4.0 star property
Hollywood
10.0 out of 10, Exceptional, (1 review)
$801 nightly
The price is $857
May 19 - May 20
Total with taxes and fees
Casa Sycamore by Oraklus
Living area

Serene Topanga Mountain Wonderland Cottage with private Creek + Trails

Serene Topanga Mountain Wonderland Cottage with private Creek + Trails
Topanga
2.0 out of 10, (1 review)
$165 nightly
The price is $165
May 7 - May 8
Total with taxes and fees
Serene Topanga Mountain Wonderland Cottage with private Creek + Trails
Exterior

Large luxury studio with view in of golf course ,

Large luxury studio with view in of golf course ,
Sunset Park
9.8 out of 10, Exceptional, (62 reviews)
"Excellent location!"
United States
Tyna J.
$260 nightly
The price is $299
May 7 - May 8
Total with taxes and fees
Large luxury studio with view in of golf course ,
Outdoor dining

Remodeled Designer Cottage with Bicycles

Remodeled Designer Cottage with Bicycles
Carlson Park
10.0 out of 10, Exceptional, (95 reviews)
"The location is fantastic!"
United States
Gili C.
$269 nightly
The price is $302
May 9 - May 10
Total with taxes and fees
Remodeled Designer Cottage with Bicycles
Pool

View Park with Private Pool

View Park with Private Pool
View Park-Windsor Hills
9.8 out of 10, Exceptional, (7 reviews)
"Pool was clean, host very helpful!"
United States
Bridget R.
$221 nightly
The price is $221
May 18 - May 19
Total with taxes and fees
View Park with Private Pool
Interior

Cozy 2-bedroom condo in peaceful studio city with AC

Cozy 2-bedroom condo in peaceful studio city with AC
Burbank
9.0 out of 10, Wonderful, (21 reviews)
"The location was great! We took an uber to Universal Studios, it was roughly an 8 minute ride. Drivers were readily available. The property was clean, well stocked, and cozy for a small family. We had a great trip and the host was responsive and pleasant."
United States
Justin
$294 nightly
The price is $294
May 18 - May 19
Total with taxes and fees
Cozy 2-bedroom condo in peaceful studio city with AC
Beach

Luxury Safari Tent in Santa Monica Mountains close to Malibu and beaches

Luxury Safari Tent in Santa Monica Mountains close to Malibu and beaches
Westlake Village
9.4 out of 10, Exceptional, (11 reviews)
"Exceptional hosts, a beautiful space, out of a story book western. The shower/bath is one of the nicest I've been to, and the exansive views are priceless. I extended by a few days, didn't want to go anywhere, just to be and look at the hills and open sky. "
United States
Erez B.
$230 nightly
The price is $230
May 11 - May 12
Total with taxes and fees
Luxury Safari Tent in Santa Monica Mountains close to Malibu and beaches
Apartment (1 Bedroom) | Front of property

Chic Marina Oasis 5 Star Amenities Central

Chic Marina Oasis 5 Star Amenities Central
3.0 star property
Marina del Rey
$406 nightly
The price is $469
May 11 - May 12
Total with taxes and fees
Chic Marina Oasis 5 Star Amenities Central
Property grounds

Hollywood's Suite

Hollywood's Suite
Hollywood
9.8 out of 10, Exceptional, (46 reviews)
"We gave this stay in Hollywood 5 stars. The parking situation was excellent, and the location was perfect—being so central made it easy to go both east and west around the city. There are great coffee shops and restaurants within walking distance; our favorites were Liberation Coffee and Pizzeria Mozza at the Melrose & Highland intersection.The place itself was very clean and had plenty of thoughtful touches, including a lovely outdoor patio. While it doesn’t have a full kitchen, the provided...
United States
Jeff S.
$209 nightly
The price is $235
Jun 1 - Jun 2
Total with taxes and fees
Hollywood's Suite
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winnetka Hotel Reviews

The LINE Hotel

The LINE Hotel

10/10 Excellent
"Great view. Accodomating."
Trenton 3-night trip
Posted 2 hours ago
The LINE Hotel

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 $155 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

Are there vacation rentals in Winnetka?

Yes, we have vacation rentals where you'll be only 13.4 mi (21.5 km) from Universal Studios Hollywood, offering you a secluded option if you want a quieter place to stay. Our travelers say Winnetka has a good selection of restaurants. Make sure you have time to check out the shopping and entertainment choices during your trip.

What are some of the best vacation rentals that Winnetka has to offer?

Kobe Bryant vacation getaway - 5 minutes to Rodeo Drive, Game console, Hot Tub: This vacation home rental outside of Winnetka offers a balcony, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Winnetka?

Choose from 14 Expedia vacation rentals in Winnetka for a memorable vacation.

What’s there to see and do in Winnetka?

While exploring the area, visit family-friendly sights like Universal Studios Hollywood, or get outside and enjoy nature at Santa Monica Beach. Six Flags Magic Mountain and Venice Beach are other popular places to visit in the area.

What’s a vacation rental in Winnetka like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Winnetka. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for families.