Short-Term Rentals in Winnetka, IL: Compare 10+ Sites & Save

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182 Best Short-Term Rentals in Winnetka (Starting from $119)

Updated Spacious Home Near Northwestern University
Updated Spacious Home Near Northwestern University
House
Wilmette, IL, USA
2.8k from Winnetka center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$242
Average price / night
Check Availability
Charming, light-filled 5br Wilmette home
Charming, light-filled 5br Wilmette home
House
Wilmette, IL, 60091, United States
2.5k from Winnetka center

AC, Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$252
Average price / night
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Ideal 1-Bedroom Apartment - Hartrey G
Ideal 1-Bedroom Apartment - Hartrey G
Apartment
Evanston, IL, USA
5.8k from Winnetka center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom2 Guests
New to Booking
$232
Average price / night
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Charming 3-bedroom house with AC and WiFi in Wilmette
Charming 3-bedroom house with AC and WiFi in Wilmette
House
Wilmette, IL, 60091, United States
2.7k from Winnetka center

AC, Crib, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$205
Average price / night
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Walk to Train Convenient Skokie Condo!
Walk to Train Convenient Skokie Condo!
Apartment
Skokie, IL, USA
6.5k from Winnetka center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Condos

1 Bedroom4 Guests
5.0

Review score

1 reviews

$192
Average price / night
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Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool!
Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool!
House
Glenview, IL, 60025, United States
2.9k from Winnetka center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms7 Guests
9.8

Exceptional

10 reviews

$383
Average price / night
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Stylish Evanston Retreat Near NU & Lakefront
Stylish Evanston Retreat Near NU & Lakefront
House
Evanston, IL, USA
6.9k from Winnetka center

Internet, Pet Friendly, Fireplace/Heating, Air Conditioner, View, Sports/Activities, Parking

1 Bedroom4 Guests
New to Booking
$392
Average price / night
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Wilmette Apartment - Close to Everything!
Wilmette Apartment - Close to Everything!
Apartment
Wilmette, IL, 60091, United States
3.1k from Winnetka center

AC, Heater, Internet, Microwave, No Smoking, TV

3 Bedrooms6 Guests
New to Booking
$185
Average price / night
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Luxury Suite at Private Beach North Shore Residence
Luxury Suite at Private Beach North Shore Residence
House
Highland Park, IL, USA
7.1k from Winnetka center

B&bs, Luxury, Cheap, Accommodations, Parking, Guest houses, Homestays, Lodgings, Vacation rentals

1 Bedroom2 Guests
9.3

Superb

3 reviews

$152
Average price / night
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Extended Stay Northbrook FHS Rental
Extended Stay Northbrook FHS Rental
House
Northbrook, IL, 60062, United States
3.7k from Winnetka center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms12 Guests
New to Booking
$365
Average price / night
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Rest and Relaxation with Game Room Morton Grove IL 3 BR House
Rest and Relaxation with Game Room Morton Grove IL 3 BR House
House
IL, USA
7.1k from Winnetka center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms11 Guests
8.0

Good

1 reviews

$347
Average price / night
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NEW! Bright Modern 3Bed 2.5Bath Evanston Home w/Parking by AllSet Turnover
NEW! Bright Modern 3Bed 2.5Bath Evanston Home w/Parking by AllSet Turnover
House
Evanston, IL, 60201, United States
4.4k from Winnetka center

AC, Heater, Internet, Microwave, No Smoking, TV

3 Bedrooms9 Guests
New to Booking
$292
Average price / night
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Morton Grove w Game Room & Huge Yard
Morton Grove w Game Room & Huge Yard
House
Morton Grove, IL, USA
7.1k from Winnetka center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms11 Guests
New to Booking
$723
Average price / night
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Cozy 2-bedroom condo in Skokie
Cozy 2-bedroom condo in Skokie
Condo
Skokie, IL, 60077, United States
4.8k from Winnetka center

AC, Dryer, Fitness Equipment, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$227
Average price / night
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Pet-Friendly Family Apartment - Near NU Campus!
Pet-Friendly Family Apartment - Near NU Campus!
Apartment
Evanston, IL, USA
7.1k from Winnetka center

Apartments, Cheap, Accommodations, Parking, Spa, Pet-friendly, Lodgings, Vacation rentals, Places to stay

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$282
Average price / night
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Townhome on the West Fork River - 3br, 3ba, Art-filled home
Townhome on the West Fork River - 3br, 3ba, Art-filled home
House
Glenview, IL, 60025, United States
4.8k from Winnetka center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$309
Average price / night
Check Availability
Modern 2 Beds Apt close Downtown
Modern 2 Beds Apt close Downtown
Apartment
Evanston, IL, USA
7.2k from Winnetka center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$237
Average price / night
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Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood
Kitschy House on a Quiet Tree Lined Street in Upscale Evanston Neighborhood
House
Evanston, IL, 60201, United States
5.2k from Winnetka center

AC, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

15 reviews

$218
Average price / night
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Family Apartment with Deck and Yard Near Northwestern
Family Apartment with Deck and Yard Near Northwestern
Apartment
Evanston, IL, USA
7.2k from Winnetka center

Apartments, Cheap, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms6 Guests
9.4

Superb

8 reviews

$119
Average price / night
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Entire home, close to highway, serene neighborhood
Entire home, close to highway, serene neighborhood
House
Northbrook, IL, 60062, United States
5.3k from Winnetka center

AC, Dryer, Heater, Internet, Laundry, No Smoking, TV, Washer

3 Bedrooms6 Guests
New to Booking
$206
Average price / night
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2 Mi to Northwestern Updated Home with Game Room!
2 Mi to Northwestern Updated Home with Game Room!
House
Evanston, IL, USA
7.3k from Winnetka center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$393
Average price / night
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1 Mi to Metra: Estate w/ Theater, Game Room & More
1 Mi to Metra: Estate w/ Theater, Game Room & More
House
Northbrook, IL, 60062, United States
5.4k from Winnetka center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Kitchen

4 Bedrooms8 Guests
New to Booking
$1264
Average price / night
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Guests Get Free Breakfast Daily! In \"The Glen\" District. Indoor Pool | Staybridge Suites
Guests Get Free Breakfast Daily! In \"The Glen\" District. Indoor Pool | Staybridge Suites
Condo
Glenview, IL, 60026, United States
5.4k from Winnetka center

AC, Barbecue, Breakfast Included, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

1 Bedroom4 Guests
New to Booking
$238
Average price / night
Check Availability
King Suite in \"The Glen\" District. Free Breakfast Daily. Indoor Pool
King Suite in \"The Glen\" District. Free Breakfast Daily. Indoor Pool
Condo
Glenview, IL, 60026, United States
5.5k from Winnetka center

AC, Barbecue, Breakfast Included, Business Services, Dryer, Elevator, Free Parking, Heater, Internet

1 Bedroom2 Guests
9.6

Exceptional

4 reviews

$230
Average price / night
Check Availability
\"The Glen\" District Suite with A/C | Business Center + Heated Indoor Pool!
\"The Glen\" District Suite with A/C | Business Center + Heated Indoor Pool!
Condo
Glenview, IL, 60026, United States
5.5k from Winnetka center

AC, Barbecue, Breakfast Included, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

2 Bedrooms5 Guests
9.2

Superb

11 reviews

$361
Average price / night
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In \"The Glen\" Business District. Free Breakfast. Indoor Pool. Studio at Staybridge.
In \"The Glen\" Business District. Free Breakfast. Indoor Pool. Studio at Staybridge.
Apartment
Glenview, IL, 60026, United States
5.5k from Winnetka center

AC, Barbecue, Breakfast Included, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

9.0

Fabulous

2 reviews

$174
Average price / night
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Gorgeous 15BD & 5.5BR House w/Ninja Gym - Skokie!
Gorgeous 15BD & 5.5BR House w/Ninja Gym - Skokie!
House
Skokie, IL, 60076, United States
5.6k from Winnetka center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

7 Bedrooms18 Guests
8.6

Fabulous

8 reviews

$1633
Average price / night
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Other accommodation types in Winnetka:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Winnetka.

Winnetka Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 182 verified short-term rentals in Winnetka, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Winnetka vary depending on location, property size, and travel dates. Rates typically start from around $119 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Winnetka include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Winnetka, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Winnetka often include amenities such as Fireplace/Heating, Internet, and Wellness Facilities, providing a comfortable and convenient stay.

Short-term rentals in Winnetka are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.