Search Vacation Homes in Winnetka

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Winnetka vacation homes

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, (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.
The price is AED 694
AED 2,271 total
includes taxes & fees
15 Dec - 16 Dec
Relaxing Getaway w/ Game Room, Pickleball & More
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 AED 426
AED 1,156 total
includes taxes & fees
11 Dec - 12 Dec
Cozy Family Hideaway, sleeps 8, yard, hikes, shops, 30 mins to beach
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 AED 962
AED 1,522 total
includes taxes & fees
11 Dec - 12 Dec
Scenic Retreat With Deck Stunning Views in LA
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, (4)
"The studio was the perfect fit for our stay! We highly recommend it to others if you need a place to stay in Burbank"
United States
Tatum S.
The price is AED 437
AED 896 total
includes taxes & fees
6 Jan - 7 January 2026
Charming stand alone guest house in Burbank close to universal studios
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 AED 349
AED 551 total
includes taxes & fees
11 Dec - 12 Dec
Mermaid Suite + Private Trails, Cave and Creek!
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 AED 507
AED 2,184 total
includes taxes & fees
11 Dec - 12 Dec
Scenic Retreat With Deck & Stunning Views in LA
Interior
Topanga Creative Suite + Private Trails & Creeks

Topanga Creative Suite + Private Trails & Creeks

Topanga Creative Suite + Private Trails & Creeks
Topanga
10.0 out of 10, Exceptional, (2)
"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.
Topanga Creative Suite + Private Trails & Creeks
Fridge, microwave, oven, stovetop
C. Glamorous NoHo Retreat near Universal & Hollywood w/Games, Hot Tub, & Parking

C. Glamorous NoHo Retreat near Universal & Hollywood w/Games, Hot Tub, & Parking

C. Glamorous NoHo Retreat near Universal & Hollywood w/Games, Hot Tub, & Parking
Los Angeles
The price is AED 261
AED 1,957 total
includes taxes & fees
11 Dec - 12 Dec
C. Glamorous NoHo Retreat near Universal & Hollywood w/Games, Hot Tub, & Parking
Fridge, oven, stovetop, dishwasher
Charming 2-bedroom house in Granada Hill- Los Angeles

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.
The price is AED 496
AED 1,300 total
includes taxes & fees
6 Jan - 7 January 2026
Charming 2-bedroom house in Granada Hill- Los Angeles
Fridge, microwave, oven, stovetop
EV Charger Prominent 5B4B Residence

EV Charger Prominent 5B4B Residence

EV Charger Prominent 5B4B Residence
Los Angeles
9.8 out of 10, Exceptional, (11)
"Check in was easy. Every room was clean. Large garage for parking. Bedrooms on every floor offers separation for guests. The house looks just like the pictures. 2 balconies, 1 in the living room and one in the top level master bedroom. Small outdoor seating would be nice. FYI: The other resident in the complex does not close the driveway gate. They leave it open. "
United States
Thomasa A.
The price is AED 502
AED 1,940 total
includes taxes & fees
15 Dec - 16 Dec
EV Charger Prominent 5B4B Residence
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

HILL SIDE GETAWAY next to Magic Mountain, and close to all theme parks
2.0 star property
Santa Clarita
10.0 out of 10, Exceptional, (3)
"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.
The price is AED 400
AED 698 total
includes taxes & fees
14 Dec - 15 Dec
HILL SIDE GETAWAY next to Magic Mountain, and close to all theme parks
Outdoor dining
The Tiny Home in Thousand Oaks

The Tiny Home in Thousand Oaks

The Tiny Home in Thousand Oaks
Thousand Oaks
9.4 out of 10, Exceptional, (6)
"Such a great spot to stay! Clean, safe and so nice! Will 100% stay here again if I'm in town."
United States
Amanda P.
The price is AED 423
AED 702 total
includes taxes & fees
11 Dec - 12 Dec
The Tiny Home in Thousand Oaks
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 AED 453
AED 754 total
includes taxes & fees
11 Dec - 12 Dec
Beautiful 1972 Classic Airstream in Santa Monica Mountains
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

Luxury Safari Tent in Santa Monica Mountains close to Malibu and beaches
Westlake Village
9.2 out of 10, Wonderful, (10)
"We loved the location, the host, the comfortable bed and the amenities, and the thoughtful touches throughout! Would definitely stay there again!"
United States
Anonymous traveler
The price is AED 496
AED 801 total
includes taxes & fees
11 Dec - 12 Dec
Luxury Safari Tent in Santa Monica Mountains close to Malibu and beaches
TV
Retro Cottage, Hot Tub, Putting Green, walk to all

Retro Cottage, Hot Tub, Putting Green, walk to all

Retro Cottage, Hot Tub, Putting Green, walk to all
Thousand Oaks
10.0 out of 10, Exceptional, (2)
"Myself and a few friends rented the Retro Cottage while we were playing in a field hockey tournament. The location was perfect because you could walk to a main strip where there were coffee shops amd plenty of restaurants. Down the road further there were high end shops and more restaurant options. We loved the hot tub at the house and the outdoor seating because we could relax and be together as a small group. The check in and check out process was very easy and the property manager was very...
United States
Kelsi L.
The price is AED 584
AED 1,653 total
includes taxes & fees
11 Dec - 12 Dec
Retro Cottage, Hot Tub, Putting Green, walk to all
Outdoor dining
Heavenly Staycation in the heart of Los Angeles

Heavenly Staycation in the heart of Los Angeles

Heavenly Staycation in the heart of Los Angeles
2.0 star property
Lake Balboa
9.8 out of 10, Exceptional, (6)
"Host was very nice place was clean and anything that we needed they took care of it"
United States
Iolanda S.
The price is AED 909
AED 2,479 total
includes taxes & fees
14 Dec - 15 Dec
Heavenly Staycation in the heart of Los Angeles
Exterior
Tiny house with AC in vibrant Los Angeles

Tiny house with AC in vibrant Los Angeles

Tiny house with AC in vibrant Los Angeles
2.0 star property
West Los Angeles
The price is AED 405
AED 787 total
includes taxes & fees
11 Dec - 12 Dec
Tiny house with AC in vibrant Los Angeles
Fridge, microwave, oven, stovetop
Over the Oaks - Great View - Whole Home - Stylish

Over the Oaks - Great View - Whole Home - Stylish

Over the Oaks - Great View - Whole Home - Stylish
Thousand Oaks
9.8 out of 10, Exceptional, (16)
"Perfect house for our little family in a nice neighbourhood!"
Germany
Michael H.
Over the Oaks - Great View - Whole Home - Stylish
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 Anza - A Calabasas Hotel

The Anza - A Calabasas Hotel

10/10 Excellent
"Great little boutique hotel!!"
Ashley 1-night trip
Posted 10 hours ago
The Anza - A Calabasas Hotel

Explore a world of travel with Expedia