Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Winnetka

Game room
Relaxing Getaway w/ Game Room, Pickleball & More

Relaxing Getaway w/ Game Room, Pickleball & More

Canoga Park
10.0 out of 10, Exceptional, (2)
"The host, Kevin, was very communicative and willing to go out of their way to accommodate my stay in any way they could. Home was exactly as described, with all the amenities imaginable, allowing my group of 7 to sleep comfortably. Couldn’t recommend this place enough!"
United States
Jason E.
$556 nightly
The price is $625
Dec 9 - Dec 10
Total with taxes and fees
Relaxing Getaway w/ Game Room, Pickleball & More
Marina
Cozy good vibes boat experience in Marina Del Rey. Perfect location in safe area

Cozy good vibes boat experience in Marina Del Rey. Perfect location in safe area

Marina del Rey
8.8 out of 10, Excellent, (50)
"Great location, great host, fun little get away!"
United States
vickey m.
$153 nightly
The price is $161
Dec 9 - Dec 10
Total with taxes and fees
Cozy good vibes boat experience in Marina Del Rey. Perfect location in safe area
Exterior detail
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)
"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.
$282 nightly
The price is $282
Dec 11 - Dec 12
Total with taxes and fees
Luxury Covered Wagon in Santa Monica Mountains close to Malibu w/ King Bed
Dining room
Gilmore One

Gilmore One

4.0 star property
Van Nuys
8.6 out of 10, Excellent, (121)
"Everything was awsome, The bulding was clean and spotless..... My secound time staying here highly recommended "
Canada
ISKANDAR
$131 nightly
The price is $150
Jan 4 - Jan 5, 2026
Total with taxes and fees
Gilmore One
Apartment | 1 bedroom
Scenic Retreat With Deck Stunning Views in LA

Scenic Retreat With Deck Stunning Views in LA

2.0 star property
Atwater Village
10.0 out of 10, Exceptional, (2)
"Good"
United States
Shantinique
$231 nightly
The price is $258
Dec 9 - Dec 10
Total with taxes and fees
Scenic Retreat With Deck Stunning Views in LA
Terrace/patio
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, (55)
"Great house in a great neighborhood! This place checks all the boxes! "
United States
Rich D.
Fabulous guest house just minutes away from anything you would need!
Fridge, microwave, oven, stovetop
Cozy Family Hideaway, sleeps 8, yard, hikes, shops, 30 mins to beach

Cozy Family Hideaway, sleeps 8, yard, hikes, shops, 30 mins to beach

Santa Susana
9.8 out of 10, Exceptional, (30)
"Spacious and well-stocked, this was a convenient place for us to stay as a family"
United States
Connor G.
$311 nightly
The price is $315
Dec 9 - Dec 10
Total with taxes and fees
Cozy Family Hideaway, sleeps 8, yard, hikes, shops, 30 mins to beach
Pool
Brand New Charming Guest House in lovely Northwest Glendale CA. Private &Quiet

Brand New Charming Guest House in lovely Northwest Glendale CA. Private &Quiet

Brockmont
10.0 out of 10, Exceptional, (5)
"Nice quiet getaway place. The place was very clean. The location is in a beautiful neighborhood surrounded by beautiful landscaping. The interior decor was aesthetically pleasing. Me and my partner will be coming back to this place when we travel to LA. The bedding was very comfortable and relaxing. The jacuzzi hot tub provided that added comfort after a long day out. Thank you for providing added memories to our life."
United States
Willie S.
$315 nightly
The price is $315
Dec 16 - Dec 17
Total with taxes and fees
Brand New Charming Guest House in lovely Northwest Glendale CA. Private &Quiet
Exterior
Topanga Mountain Retreat - The Wonderland Cabin

Topanga Mountain Retreat - The Wonderland Cabin

Topanga
9.2 out of 10, Wonderful, (26)
"Such a wonderful stay and the host made us feel so welcome and it was so easy to get acclimated. Such a beautiful, quaint property. Definitely a must stay."
United States
Sophie S.
Topanga Mountain Retreat - The Wonderland Cabin
House, 1 Queen Bed, Patio, Mountain View (1733 Los Angeles) | Living area | 42-inch flat-screen TV with digital channels
Scenic Retreat With Deck & Stunning Views in LA

Scenic Retreat With Deck & Stunning Views in LA

3.5 star property
Atwater Village
$577 nightly
The price is $594
Dec 9 - Dec 10
Total with taxes and fees
Scenic Retreat With Deck & Stunning Views in LA
Interior
Mermaid Suite + Private Trails, Cave and Creek!

Mermaid Suite + Private Trails, Cave and Creek!

Topanga
8.6 out of 10, Excellent, (7)
"Wonder place to stay to get out of the city for a great price… would definitely stay again. "
United States
Douglas W.
$150 nightly
The price is $150
Dec 10 - Dec 11
Total with taxes and fees
Mermaid Suite + Private Trails, Cave and Creek!
Pool
View Park Angeles with Private Pool

View Park Angeles with Private Pool

View Park-Windsor Hills
9.8 out of 10, Exceptional, (7)
"Really enjoyed our stay. Location was perfect for us. Had a great time. Easy check in process. Everything was as described. Unfortunately it was too cool to use the pool but will be back again. "
United States
Deb G.
$231 nightly
The price is $231
Dec 9 - Dec 10
Total with taxes and fees
View Park Angeles with Private Pool
Exterior
Topanga Japanese Tea House + Private Creek + Mountain Trails.

Topanga Japanese Tea House + Private Creek + Mountain Trails.

Topanga
9.0 out of 10, Wonderful, (47)
"We really enjoyed our stay here at the Japanese Tea House! We would love to have the opportunity to stay here again. "
United States
natalie c.
$180 nightly
The price is $180
Jan 7 - Jan 8, 2026
Total with taxes and fees
Topanga Japanese Tea House + Private Creek + Mountain Trails.
Dining
5 MIN TO LAX, Private entrance studio apartment. Pet friendly apartment

5 MIN TO LAX, Private entrance studio apartment. Pet friendly apartment

Fox Hills
9.6 out of 10, Exceptional, (19)
"We will be staying there again. Thank you."
United States
Michelle
$182 nightly
The price is $182
Dec 9 - Dec 10
Total with taxes and fees
5 MIN TO LAX, Private entrance studio apartment. Pet friendly apartment
Exterior
Beautiful 1972 Classic Airstream in Santa Monica Mountains

Beautiful 1972 Classic Airstream in Santa Monica Mountains

Thousand Oaks
8.8 out of 10, Excellent, (34)
"Excellent Santa Monica mountain's location Meggan and her husband provided excellent directions and instructions. Great place to stay, wish I had more time to spend there."
United States
Patrick D.
$205 nightly
The price is $205
Dec 9 - Dec 10
Total with taxes and fees
Beautiful 1972 Classic Airstream in Santa Monica Mountains
Outdoor spa tub
Luxury Casita with Top-Tier Jacuzzi

Luxury Casita with Top-Tier Jacuzzi

2.0 star property
Studio Village
$285 nightly
The price is $285
Dec 10 - Dec 11
Total with taxes and fees
Luxury Casita with Top-Tier Jacuzzi
Property grounds
Large luxury studio with view in of golf course

Large luxury studio with view in of golf course

2.0 star property
Sunset Park
9.8 out of 10, Exceptional, (61)
"Excellent location!"
United States
Tyna J.
$333 nightly
The price is $382
Dec 9 - Dec 10
Total with taxes and fees
Large luxury studio with view in of golf course
Fridge, oven, stovetop, dishwasher
Charming 2-bedroom house in Granada Hill- Los Angeles

Charming 2-bedroom house in Granada Hill- Los Angeles

2.0 star property
Granada Hills South
9.4 out of 10, Exceptional, (9)
"Clean, comfortable and cozy.Way better than staying at a hotel.You have your privacy and a lot of commodities."
United States
Eddie V.
$322 nightly
The price is $362
Dec 28 - Dec 29
Total with taxes and fees
Charming 2-bedroom house in Granada Hill- Los Angeles
Living area
Historic 1914 Stone Cabin + Private Trails & Creek

Historic 1914 Stone Cabin + Private Trails & Creek

Topanga
9.2 out of 10, Wonderful, (16)
"Such a wonderful getaway. I enjoyed the nature, the silence, the whimsical decor. Will be happy to stay again if I have the chance."
United States
Shantha S.
Historic 1914 Stone Cabin + Private Trails & Creek
Outdoor dining
Studio Mins to Venice Beach, Sony Studios, LAX & Vibrant Downtown Culver City

Studio Mins to Venice Beach, Sony Studios, LAX & Vibrant Downtown Culver City

Washington Culver
9.2 out of 10, Wonderful, (30)
"Amazing stay after a long day of beach volleyball! Great place to relax for the evening!! Great breakfast spots around for in the morning! Access to TV streaming services too made for such a great stay! "
United States
Alexa S.
$210 nightly
The price is $224
Dec 10 - Dec 11
Total with taxes and fees
Studio Mins to Venice Beach, Sony Studios, LAX & Vibrant Downtown Culver City
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

Loews Hollywood Hotel

Loews Hollywood Hotel

10/10 Excellent
"AMAZING "
Jamel 4-night trip
Posted 1 day ago
Loews Hollywood 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 $150 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?

Santa Monica Beach House: This vacation home rental outside of Winnetka is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Santa Monica Pier 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.