Winnetka Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

26 Houses

(19) Excellent 

8

Just north of Chicago

Illinois / Winnetka

Winnetka cottage

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden
“Comfortable and Convenient” Maggi greeted us pleasantly as soon as we arrived. The rental home was just as we expected. It was clean and had everything we needed for a "home base" while we visited the area. Lake Michigan is very close which is a bi
…see more

Price per night from

$126

Responds fast!
avg. 3 hours 40 minutes

Price per night from

$126

Great rentals within 20 miles that match your search

Distance approx 15.67 km from Winnetka

(1) Excellent 

14

Oak Park Beauty Sleeps 1 to 8 Guests

Illinois / Oak Park

Oak Park apartment

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$161

Responds fast!
avg. 2 hours 1 minutes

Price per night from

$161

Distance approx 13.37 km from Winnetka

16

Rare! Spacious Private 5 Beds for the Holidays

Lake County / Buffalo Grove

Buffalo Grove house

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Child Friendly

Price per night from

$314

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$314

Distance approx 16.7 km from Winnetka

(3) Very Good 

20

Oak Park Bungalow

Illinois / Oak Park

Oak Park house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$241

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$241

Distance approx 16.75 km from Winnetka

11

Make It Your Own - 15 Minutes to Chicago

Illinois / Forest Park

Forest Park apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$125

Price per night from

$125

Distance approx 15.87 km from Winnetka

4

Condo

Illinois / Oak Park

Oak Park house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Air conditioning

Price per night from

$509

Price per night from

$509

Distance approx 15.93 km from Winnetka

(1) Excellent 

13

Charming apartment, fantastic location! Spacious 4 bedroom, a rare find!

Illinois / Forest Park

Forest Park apartment

4 5 1 night min

  • 4 bedrooms
  • sleeps 5
  • 1 night min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$171

Responds fast!
avg. 1 hour 1 minutes

Price per night from

$171

Distance approx 2.16 km from Winnetka Show on Map

(2) Excellent 

30

Beautifully Remodeled 3 BR Townhouse near Chicago

Illinois / Wilmette

Wilmette townhouse

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$149

Responds fast!
avg. 1 hour 10 minutes

Price per night from

$149

Distance approx 10.65 km from Winnetka

(3) Very Good 

27

Completely Remodeled 3-Bedroom House!

Illinois / Wheeling

Wheeling house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$137

Responds fast!
avg. 1 hour 10 minutes

Price per night from

$137

Distance approx 19.45 km from Winnetka

8

Take A Pebble Apartments (Studio)

Lake County / Lake Zurich

Lake Zurich apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning

Price per night from

$113

Price per night from

$113

Distance approx 6.51 km from Winnetka Show on Map

15

Sleep Aboard Adeline’s Sea Moose: 68 ft Private Yacht Rentals Chicago Downtown

Illinois / Lincolnwood

Lincolnwood yacht

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$1,369

Price per night from

$1,369

Distance approx 11.25 km from Winnetka

23

Vintage 3BR in Lake View by Sonder

Illinois / Lincolnwood

Lincolnwood apartment

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$57

Responds fast!
avg. 43 minutes

Price per night from

$57

Distance approx 16.01 km from Winnetka

16

Newly Remodeled Modern Apartment

Illinois / Melrose Park

Melrose Park apartment

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly

Price per night from

$184

Responds fast!
avg. 50 minutes

Price per night from

$184

Distance approx 5.99 km from Winnetka Show on Map

20

Highland Park Luxury Home- 2000 square foot Suite

Lake County / Highland Park

Highland Park b and b

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Car not necessary
  • Air conditioning

Price per night from

$114

Price per night from

$114

Distance approx 8.24 km from Winnetka Show on Map

24

Luxe Chicago Townhome w/ Balcony - 20 Mins to DT!

Illinois / Lincolnwood

Lincolnwood house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Air conditioning

Price per night from

$144

Responds fast!
avg. 9 minutes

Price per night from

$144

Distance approx 16.26 km from Winnetka

9

Cozy master bedroom in Oak Park Arts district

Illinois / Oak Park

Oak Park house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Car not necessary
  • Air conditioning
  • Private garden

Price per night from

$81

Price per night from

$81

Distance approx 4.2 km from Winnetka Show on Map

7

Pinewoods Retreat - Private Room

Illinois / Evanston

Evanston room

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$59

Price per night from

$59

Distance approx 16.05 km from Winnetka

17

Cute, cozy modern apartment 20 min ohare and midway airports and 30 min to dt

Illinois / Melrose Park

Melrose Park apartment

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Air conditioning

Price per night from

$161

Responds fast!
avg. 50 minutes

Price per night from

$161

Distance approx 11.25 km from Winnetka

(1) Excellent 

18

Handsome 3BR in Lake View by Sonder

Illinois / Lincolnwood

Lincolnwood apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$62

Responds fast!
avg. 43 minutes

Price per night from

$62

Distance approx 6.04 km from Winnetka Show on Map

22

Hull Chateau

Illinois / Evanston

Evanston house

2 7 1 night min

  • 2 bedrooms
  • sleeps 7
  • 1 night min
  • Nearest beach 2 mi
  • Child Friendly
  • Car not necessary

Price per night from

$255

Price per night from

$255

Distance approx 9.43 km from Winnetka

24

Opulent Historic 2BR Apartment in Andersonville w/ Contemporary Kitchen

Illinois / Lincolnwood

Lincolnwood apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$173

Price per night from

$173

Distance approx 9.42 km from Winnetka

29

Elegantly Updated Albany Park 4BR/3.5BA w/ Private Fenced Yard & Garage

Illinois / Lincolnwood

Lincolnwood house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$263

Price per night from

$263

Distance approx 11.55 km from Winnetka

21

Grand 3BR in Roscoe Village by Sonder

Illinois / Lincolnwood

Lincolnwood condo

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$132

Responds fast!
avg. 43 minutes

Price per night from

$132

Distance approx 8.52 km from Winnetka

33

Exquisite Interior Designer’s House Short Walk to Lake Michigan

Lake County / Highwood

Highwood house

4 6 min stay varies

  • 4 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0.5 mi
  • Child Friendly
  • Air conditioning

Price per night from

$458

Price per night from

$458

Distance approx 13.25 km from Winnetka

12

Comfy Quarters

Illinois / River Grove

River Grove house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Car not necessary
  • Air conditioning
  • Private garden

Price per night from

$103

Price per night from

$103

Distance approx 13.86 km from Winnetka

9

OAK PARK BEAUTIFUL, HISTORICAL, CONVENIENT TO PUBLIC TRANSPORTATION, AIRPORTS

Illinois / Oak Park

Oak Park b and b

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$40

Responds fast!
avg. 3 hours 44 minutes

Price per night from

$40