House
10.0(16 Reviews)
3 Bedrooms
6 Guests
Child Friendly
US $383/Night
7 Nights - US $2,680
Winnetka Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Winnetka
10.0
New
House
2 Bedrooms
6 Guests
Parking- Child Friendly
Security/Safety
Guest Services
US $258/Night
7 Nights - US $1,808
Hotel
9.2(704 Reviews)
Breakfast- Parking
Pool
Balcony/Terrace
US $192/Night
7 Nights - US $1,346
Apartment
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Parking
Kitchen
Air Conditioner
Internet
US $233/Night
7 Nights - US $1,629
Hotel
9.2(119 Reviews)
Private Pool- Breakfast
- Parking
- Pool
US $229/Night
7 Nights - US $1,604
House
10.0(1 Review)
5 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $231/Night
7 Nights - US $1,616
House
9.8(10 Reviews)
4 Bedrooms
- Private Pool
- Parking
- Pool
Ocean View
US $316/Night
7 Nights - US $2,209
House
3 Bedrooms
6 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
US $256/Night
7 Nights - US $1,794
US $247/Night
7 Nights - US $1,732
Luxury Holiday Rentals in Winnetka
Over 32+ Luxury Holiday Rentals in or Near Winnetka
House
6 Bedrooms
12 Guests
US $1,490/Night
7 Nights - US $10,428
US $209/Night
7 Nights - US $1,463
House
3 Bedrooms
9 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $187/Night
7 Nights - US $1,306
US $168/Night
7 Nights - US $1,173
Hotel
7.9(187 Reviews)
- Breakfast
- Parking
- Balcony/Terrace
- Air Conditioner
US $155/Night
7 Nights - US $1,085
Hotel
8.6(1007 Reviews)
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $152/Night
7 Nights - US $1,063
Hotel
8.7(698 Reviews)
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $144/Night
7 Nights - US $1,010
Hotel
6.5(377 Reviews)
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $108/Night
7 Nights - US $754
Hotel
6.8(1006 Reviews)
- Breakfast
- Kitchen
- Air Conditioner
- Internet
US $107/Night
7 Nights - US $746
Top-Rated Holiday Rentals with a Pool in Winnetka
Over 2+ The Best Private Villas and Holiday Rentals in Winnetka with a Pool
House
10.0(2 Reviews)
4 Bedrooms
8 Guests
Oceanfront- Pool
Spa- Ocean View
US $800/Night
7 Nights - US $5,600
House
1 Bedroom
2 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $241/Night
7 Nights - US $1,687
Pet-Friendly Holiday Rentals in Winnetka
Over 17+ Pet-Friendly Holiday Rentals in or Near Winnetka
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
Laundry
US $228/Night
7 Nights - US $1,595
Apartment
2 Bedrooms
3 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $140/Night
7 Nights - US $980
House
10.0(7 Reviews)
4 Bedrooms
7 Guests
- Oceanfront
Hot Tub- Breakfast
- Parking
US $1,240/Night
7 Nights - US $8,679
House
10.0(3 Reviews)
3 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $267/Night
7 Nights - US $1,866
US $504/Night
7 Nights - US $3,530
US $340/Night
7 Nights - US $2,383
House
3 Bedrooms
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $278/Night
7 Nights - US $1,945
Villa
5 Bedrooms
7 Guests
- Breakfast
- Ocean View
- Balcony/Terrace
View
US $894/Night
7 Nights - US $6,257
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $157/Night
7 Nights - US $1,097
Large Holiday Rentals and Private Villas in Winnetka
Over 3+ Large Holiday Rentals and Private Villas in or Near Winnetka
Villa
4 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,629/Night
7 Nights - US $11,403
US $363/Night
7 Nights - US $2,541
US $325/Night
7 Nights - US $2,275
Wheelchair Accessible Holiday Homes in Winnetka
Over 1+ Wheelchair Accessible Holiday Homes in or Near Winnetka
Apartment
2.0(1 Review)
1 Bedroom
5 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $199/Night
7 Nights - US $1,393
Winnetka Private Villas and Holiday Homes Under $200
Over 2+ Winnetka Private Villas and Holiday Homes Under $200
US $200/Night
7 Nights - US $1,400
House
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $135/Night
7 Nights - US $945
Instantly Bookable Holiday Homes in Winnetka
Over 1+ Instantly Bookable Holiday Homes in or Near Winnetka
House
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Laundry
US $341/Night
7 Nights - US $2,386
Book a Last Minute Place to Stay in Winnetka
About Casai's Private Villas and Holiday Rentals in Winnetka
Discover more than 41 vacation rentals available in Winnetka. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winnetka.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winnetka, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winnetka. On average, places to stay near Winnetka offer 675.57 ft², with nightly prices averaging US $372.
With Casai, finding and comparing holiday rentals in Winnetka is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Winnetka, IL
There are 41 Winnetka, IL Holiday Rentals
- Prices for a holiday home in Winnetka start at US $107
- Top rated vacation home in Winnetka is Warm and Cheerful 3 Bedroom Winnetka Townhouse
- Most popular short term in Winnetka is Renaissance Chicago North Shore Hotel
- Cheapest place to stay in Winnetka is Extended Stay America Suites Chicago Skokie
- Most expensive holiday rental in Winnetka is 6BD/7BA Near Downtown Chicago w/ Game room. Close to Northwestern University
Frequently Asked Questions About Winnetka?
What are the top holiday rentals in Winnetka?
With numerous options available in Winnetka, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winnetka:
- Warm and Cheerful 3 Bedroom Winnetka Townhouse
- Wilmette Apartment - Centrally Located!
- Charming, light-filled 5br Wilmette home
- Fabulous 4-bedroom house with Inground Pool! On quiet cul-de-sac.
- Residence Inn by Marriott Chicago Wilmette/Skokie
- Residence Inn by Marriott Chicago Wilmette/Skokie
- Hampton Inn & Suites Chicago North Shore
- Renaissance Chicago North Shore Hotel
- Sheraton Chicago Northbrook Hotel
- Sheraton Chicago Northbrook
Which holiday homes in Winnetka are best for families?
If you're searching for a family-friendly holiday home in Winnetka, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winnetka:
How many Casai.nz holiday rentals are available in Winnetka?
As of 2026, Casai boasts over 41 properties listed in the Winnetka area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winnetka.
