Winnetka Vacation Rentals

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Check prices for these dates

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Winnetka vacation rentals

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

Relaxing Getaway w/ Game Room, Pickleball & More

Relaxing Getaway w/ Game Room, Pickleball & More
Canoga Park
10.0 out of 10, Exceptional, (3)
"Host was very responsive. Lovely, very clean home. We stayed for a week for Thanksgiving. Convenient to shops and restaurants. Would definitely stay again. "
United States
Lisa F.
The price is ￥30,907
￥98,624 total
includes taxes & fees
Jan 19 - Jan 20, 2026
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

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.
The price is ￥16,510
￥24,276 total
includes taxes & fees
Dec 30 - Dec 31
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

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.
The price is ￥31,314
￥46,032 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Luxury Covered Wagon in Santa Monica Mountains close to Malibu w/ King Bed
Dining room
Gilmore One

Gilmore One

Gilmore One
4.0 star property
Van Nuys
8.6 out of 10, Excellent, (124)
"Everything was awsome, The bulding was clean and spotless..... My secound time staying here highly recommended "
Canada
ISKANDAR
The price is ￥12,436
￥23,102 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Gilmore One
Terrace/patio
Fabulous guest house just minutes away from anything you would need!

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.
The price is ￥21,568
￥37,582 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Fabulous guest house just minutes away from anything you would need!
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

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.
The price is ￥27,965
￥49,200 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Brand New Charming Guest House in lovely Northwest Glendale CA. Private &Quiet
Apartment | 1 bedroom
Scenic Retreat With Deck Stunning Views in LA

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, (3)
"Good"
United States
Shantinique
The price is ￥26,144
￥48,221 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Scenic Retreat With Deck Stunning Views in LA
Exterior detail
*Self check-in. Private Entrance. Netflix.*

*Self check-in. Private Entrance. Netflix.*

*Self check-in. Private Entrance. Netflix.*
West Hills
9.2 out of 10, Wonderful, (17)
"GREAT stay! Quaint, cozy room/bathroom that had everything I needed. Excellent location! Owner very responsive! "
United States
Yvette F.
The price is ￥12,839
￥33,118 total
includes taxes & fees
Jan 1 - Jan 2, 2026
*Self check-in. Private Entrance. Netflix.*
Interior
Charming stand alone guest house in Burbank close to universal studios

Charming stand alone guest house in Burbank close to universal studios

Charming stand alone guest house in Burbank close to universal studios
Burbank
10.0 out of 10, Exceptional, (5)
The price is ￥18,632
￥38,203 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Charming stand alone guest house in Burbank close to universal studios
Pool
View Park Angeles with Private 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.
The price is ￥19,023
￥35,619 total
includes taxes & fees
Jan 5 - Jan 6, 2026
View Park Angeles with Private Pool
Interior
Mermaid Suite + Private Trails, Cave and Creek!

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.
The price is ￥17,223
￥25,991 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Mermaid Suite + Private Trails, Cave and Creek!
Exterior
Topanga Japanese Tea House + Private Creek + Mountain Trails.

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.
The price is ￥19,518
￥28,262 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Topanga Japanese Tea House + Private Creek + Mountain Trails.
Terrace/patio
"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

"The Best" Jacuzzi View Private Luxury Guest Cottage-Better than a Room or Suite
2.5 star property
Thousand Oaks
10.0 out of 10, Exceptional, (33)
"Great place "
United States
Gary S.
The price is ￥31,228
￥54,649 total
includes taxes & fees
Jan 2 - Jan 3, 2026
"The Best" Jacuzzi View Private Luxury Guest Cottage-Better than a Room or Suite
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

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.
The price is ￥18,128
￥49,312 total
includes taxes & fees
Dec 30 - Dec 31
Cozy Family Hideaway, sleeps 8, yard, hikes, shops, 30 mins to beach
Fridge, microwave, oven, stovetop
This apartment is a 2 bedroom(s), 2 bathrooms, located in Santa Clarita, CA.

This apartment is a 2 bedroom(s), 2 bathrooms, located in Santa Clarita, CA.

This apartment is a 2 bedroom(s), 2 bathrooms, located in Santa Clarita, CA.
Santa Clarita
10.0 out of 10, Exceptional, (12)
"Really nice, safe property. Close to restaurants, stores and the park. "
United States
Lara S.
The price is ￥21,611
￥51,672 total
includes taxes & fees
Jan 5 - Jan 6, 2026
This apartment is a 2 bedroom(s), 2 bathrooms, located in Santa Clarita, CA.
Exterior
Beautiful 1972 Classic Airstream in Santa Monica Mountains

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.
The price is ￥22,703
￥36,325 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Beautiful 1972 Classic Airstream in Santa Monica Mountains
Exterior
Remodeled Stylish Culver Cottage + Parking

Remodeled Stylish Culver Cottage + Parking

Remodeled Stylish Culver Cottage + Parking
Carlson Park
10.0 out of 10, Exceptional, (86)
"Cute place ! Everything you need in the unit or within walking distance "
United States
Joshua H.
The price is ￥24,112
￥49,454 total
includes taxes & fees
Dec 28 - Dec 29
Remodeled Stylish Culver Cottage + Parking
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

Scenic Retreat With Deck & Stunning Views in LA
3.5 star property
Atwater Village
The price is ￥24,806
￥96,485 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Scenic Retreat With Deck & Stunning Views in LA
Beach
Cozy Home W/Pool & GYM + Parking 10min to Cedars

Cozy Home W/Pool & GYM + Parking 10min to Cedars

Cozy Home W/Pool & GYM + Parking 10min to Cedars
Mid-Wilshire
9.0 out of 10, Wonderful, (6)
"Fantastic, central location. Parking included. Fabulous amenities. Responsive owners. We will definitely attempt to stay here again next time we’re in LA. "
United States
John G.
The price is ￥21,607
￥53,735 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy Home W/Pool & GYM + Parking 10min to Cedars
Exterior
Remodeled Designer Cottage with Bicycles

Remodeled Designer Cottage with Bicycles

Remodeled Designer Cottage with Bicycles
Carlson Park
10.0 out of 10, Exceptional, (89)
"Overall great stay. Easy to get in and out, easy communication, great location."
United States
Edgar C.
The price is ￥22,828
￥47,834 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Remodeled Designer Cottage with Bicycles
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

The Garland

The Garland

10/10 Excellent
"Everything was great "
lisamarie 1-night trip
Posted 17 hours ago
The Garland

Find out more about Winnetka

Search for holiday rentals in Winnetka on Expedia! You can easily find your home rentals, villas, holiday apartments in Winnetka using one of the methods below:

  • View our selection of featured holiday rentals in Winnetka
  • Use the map to find apartments and other holiday homes in the Winnetka neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winnetka while they last

Look no further and take a look at our great range of rental properties in Winnetka!

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?

Heart of Hollywood ★ 2 Car Private Parking ★ Walk To Attractions!: This vacation home rental outside of Winnetka is located in the city center and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Winnetka?

Choose from 13 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. Santa Monica Pier and Six Flags Magic Mountain 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.