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Our top choices for Winnetka holiday rentals

1. Relaxing Getaway w/ Game Room, Pickleball & More

Relaxing Getaway w/ Game Room, Pickleball & More
Canoga Park
10.0 out of 10, Exceptional, (7 reviews)
"Lovely stay. Kids really enjoyed the game room. House was clean and as advertised. Very easy check-in process. Kevin was an excellent communicator. I would highly recommend this place."
United States
Adel
The price is £537
includes taxes & fees
10 Nov - 11 Nov
Relaxing Getaway w/ Game Room, Pickleball & More

2. The Stagg Lane Retreat

The Stagg Lane Retreat
Los Angeles
9.2 out of 10, Wonderful, (5 reviews)
"We had an amazing stay here! The host was incredibly friendly, responsive, and helpful throughout our trip. The house was clean, cozy, and had everything our family needed for a comfortable stay. We especially loved that it was located in a gated neighborhood, which made us feel extra safe and gave us added peace of mind during our stay. We had no issues at all and truly enjoyed our time here. We would definitely stay here again and highly recommend it to anyone looking for a great place to...
United States
Yanelis M.
The Stagg Lane Retreat

3. Serene Topanga Mountain Wonderland Cottage with private Creek + Trails

Serene Topanga Mountain Wonderland Cottage with private Creek + Trails
Topanga
8.0 out of 10, Very good, (5 reviews)
"Great location, nice for a quick stay. Lots of good amenities. Overall pretty clean, the only issue was the bath tub, it was rather dirty upon arrival with what seemed like pet fur. There was a lot of white hairs all over the floor of the tub but other than that it was a good stay. Host is nice and communicates well."
United States
Keyrdra O.
The price is £111
includes taxes & fees
16 Nov - 17 Nov
Serene Topanga Mountain Wonderland Cottage with private Creek + Trails

4. Mermaid Suite + Private Trails, Cave and Creek!

Mermaid Suite + Private Trails, Cave and Creek!
Topanga
9.2 out of 10, Wonderful, (22 reviews)
"Unique and artsy room, very much in the spirit of "glamping." We originally stayed in Topanga to be close to Malibu at a better rate, but were pleasantly surprised to find Topanga a lot more fun than Malibu, a little gem of a town with great cafes."
United States
Elizabeth
The price is £114
includes taxes & fees
8 Nov - 9 Nov
Mermaid Suite + Private Trails, Cave and Creek!

5. Topanga Creative Suite + Private Trails & Creeks

Topanga Creative Suite + Private Trails & Creeks
Topanga
8.8 out of 10, Excellent, (17 reviews)
"Thank you for the stay."
United States
Mickey
The price is £111
includes taxes & fees
16 Nov - 17 Nov
Topanga Creative Suite + Private Trails & Creeks

6. 4 Bedroom Encino Home, Amazing Yard, Near Freeways and Attractions

4 Bedroom Encino Home, Amazing Yard, Near Freeways and Attractions
Encino Village
9.8 out of 10, Exceptional, (79 reviews)
"Very clean property, host was super helpful and responsive. Would highly recommend and would definitely stay here again!"
United States
Berj K.
The price is £372
includes taxes & fees
16 Nov - 17 Nov
4 Bedroom Encino Home, Amazing Yard, Near Freeways and Attractions

7. THE Zen Treehouse Retreat- Great Views and Peaceful Decks!

THE Zen Treehouse Retreat- Great Views and Peaceful Decks!
Los Angeles
10.0 out of 10, Exceptional, (72 reviews)
"this was one of the best rentals i’ve ever stayed at. everything about the place was thoughtful and relaxing."
United States
Jason T.
The price is £552
includes taxes & fees
9 Nov - 10 Nov
THE Zen Treehouse Retreat- Great Views and Peaceful Decks!

8. Artistic Dragonfly House with deck + private creek and trails to explore!

Artistic Dragonfly House with deck + private creek and trails to explore!
Topanga
9.8 out of 10, Exceptional, (23 reviews)
"Unique place with a great view, we enjoyed it!"
United States
Josh G.
The price is £131
includes taxes & fees
7 Dec - 8 Dec
Artistic Dragonfly House with deck + private creek and trails to explore!

9. Kasa Sunset Los Angeles

Kasa Sunset Los Angeles
3.0 star property
Hollywood
9.2 out of 10, Wonderful, (442 reviews)
"Lots of things to do nearby, lots of space, kind of loud from the noise outside but they give you ear plugs for when you are trying to sleep"
United States
Michaela
The price is £116
includes taxes & fees
16 Nov - 17 Nov
Kasa Sunset Los Angeles

10. Panoramic Loft with Deck, Private Trails and Creek

Panoramic Loft with Deck, Private Trails and Creek
Topanga
9.4 out of 10, Exceptional, (16 reviews)
"Good stay. The deck was great for mining’s and evenings with coffee/wine. Nice to be away and somewhere secluded but still have stores and restaurants nearby. Bed was very comfy and cool nights with window open."
United States
Laura Beth G.
The price is £111
includes taxes & fees
15 Nov - 16 Nov
Panoramic Loft with Deck, Private Trails and Creek

11. Topanga 3 bdrm/2ba mountain view home with huge deck.

Topanga 3 bdrm/2ba mountain view home with huge deck.
Sylvia Park
9.4 out of 10, Exceptional, (24 reviews)
"1"
United States
Kelly
The price is £326
includes taxes & fees
9 Nov - 10 Nov
Topanga 3 bdrm/2ba mountain view home with huge deck.

12. Modern Tiny House Retreat w/ Sauna, Fire Pit & Workspace

Modern Tiny House Retreat w/ Sauna, Fire Pit & Workspace
Newhall
9.6 out of 10, Exceptional, (9 reviews)
"Hosts went above and beyond will definitely stay here again!"
United States
joseph m.
The price is £113
includes taxes & fees
9 Nov - 10 Nov
Modern Tiny House Retreat w/ Sauna, Fire Pit & Workspace

13. Sherman Oaks Cozy Guest House

Sherman Oaks Cozy Guest House
Sherman Oaks
9.6 out of 10, Exceptional, (27 reviews)
"We had a wonderful stay. We will stay here again in the future."
United States
Justin E.
The price is £226
includes taxes & fees
18 Nov - 19 Nov
Sherman Oaks Cozy Guest House

14. Fenix Hotel Hollywood

Fenix Hotel Hollywood
4.0 star property
Hollywood
8.6 out of 10, Excellent, (532 reviews)
"Clean, nice room, nice staff, great location"
United Kingdom
Maria
The price is £110
includes taxes & fees
6 Dec - 7 Dec
Fenix Hotel Hollywood

15. Mountain Retreat Japanese Tea House + Private Creek and Trails

Mountain Retreat Japanese Tea House + Private Creek and Trails
Topanga
8.4 out of 10, Very good, (12 reviews)
"Great little get away spot!"
United States
David N.
The price is £123
includes taxes & fees
8 Nov - 9 Nov
Mountain Retreat Japanese Tea House + Private Creek and Trails

16. 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
9.8 out of 10, Exceptional, (11 reviews)
"Great little place close our kids! "
United States
Cindy J.
The price is £117
includes taxes & fees
10 Nov - 11 Nov
HILL SIDE GETAWAY next to Magic Mountain, and close to all theme parks

17. Woodland Hills Cottage on beautiful 1/4 acre property

Woodland Hills Cottage on beautiful 1/4 acre property
Los Angeles
10.0 out of 10, Exceptional, (18 reviews)
"Amazing getaway place and wonderful host!"
United States
Gary
The price is £561
includes taxes & fees
11 Nov - 12 Nov
Woodland Hills Cottage on beautiful 1/4 acre property

18. Malibu Beach Paradise Apartments

Malibu Beach Paradise Apartments
3.5 star property
Eastern Malibu
8.6 out of 10, Excellent, (249 reviews)
"The view of the ocean was incredible and the location walking distance to the pier"
United States
Joe
The price is £284
includes taxes & fees
7 Nov - 8 Nov
Malibu Beach Paradise Apartments

19. Granada Hills Estate | Lap Pool, Spa & Guesthouse

Granada Hills Estate | Lap Pool, Spa & Guesthouse
Granada Hills South
9.0 out of 10, Wonderful, (21 reviews)
"Beautiful home, clean and comfortable. All the amenities were great. "
United States
Arsen T.
The price is £872
includes taxes & fees
9 Nov - 10 Nov
Granada Hills Estate | Lap Pool, Spa & Guesthouse

20. The Sanctuary - Be Pampered - Full Kitchen

The Sanctuary - Be Pampered - Full Kitchen
Burbank
9.8 out of 10, Exceptional, (161 reviews)
"We can’t say enough about this property! We loved our stay here and are so very grateful to our hosts for their help, recommendations and communication. "
United States
Melissa G.
The price is £136
includes taxes & fees
8 Nov - 9 Nov
The Sanctuary - Be Pampered - Full Kitchen
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

Find out more about Winnetka

Everything you need to know about Winnetka holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winnetka holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winnetka holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winnetka holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winnetka holiday rentals we have selected for you start as low as £110 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winnetka rentals

At Expedia, we put the best Winnetka holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Winnetka?

Yes, you can find holiday rentals where you'll be only 13.4 mi (21.5 km) from Universal Studios Hollywood, providing a more remote option if you'd like a quiet spot to stay. Our travellers 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 holiday rentals that Winnetka has to offer?

Cute house a block to beach w/ two bikes pet friendly!: This holiday home rental outside of Winnetka is located on the beach, and has a BBQ, a selection of books and free WiFi to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Winnetka?

Choose from 18 Expedia holiday rentals in Winnetka for a memorable holiday.

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 holiday rental in Winnetka like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winnetka. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a family trip or a small group gathering.