Winnetka Station holiday lettings
We found 3,436 holiday rentals — enter your dates for availability
Choose the perfect holiday home within close proximity to Winnetka Station. Holiday homes offer the best amenities for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Winnetka Station
Showing deals for:14 Nov - 21 Nov
Image gallery for HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
9.29.2 out of 10 rating
Wonderful
(50 reviews)
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Chicago, IL
12% off
Price is £1,414
£1,414
£202 per night
includes taxes & fees
Image gallery for River North's Rock N' Roll - In The Heart of the City
9.69.6 out of 10 rating
Exceptional
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
7% off
Price is £2,454
£2,454
£351 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(16 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, IL
7% off
Price is £3,959
£3,959
£566 per night
includes taxes & fees
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
1010 out of 10 rating
Exceptional
(22 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
22% off
Price is £15,688
£15,688
£2,241 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, IL
7% off
Price is £2,388
£2,388
£341 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.29.2 out of 10 rating
Wonderful
(13 reviews)
3BR Luxury Modern Apartment
Chicago, IL
7% off
Price is £2,411
£2,411
£344 per night
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(57 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, IL
7% off
Price is £2,656
£2,656
£379 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, IL
7% off
Price is £2,762
£2,762
£395 per night
includes taxes & fees
Image gallery for Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
9.09.0 out of 10 rating
Wonderful
(15 reviews)
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
Chicago, IL
7% off
Price is £5,000
£5,000
£714 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, IL
7% off
Price is £1,954
£1,954
£279 per night
includes taxes & fees
Image gallery for Chic & Historic Apartment Steps from Mag Mile
9.89.8 out of 10 rating
Exceptional
(40 reviews)
Chic & Historic Apartment Steps from Mag Mile
Chicago, IL
6% off
Price is £946
£946
£135 per night
includes taxes & fees
Image gallery for Brownstone in Gold Coast - Downtown
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Brownstone in Gold Coast - Downtown
Chicago, IL
13% off
Price is £811
£811
£116 per night
includes taxes & fees
Image gallery for Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
1010 out of 10 rating
Exceptional
(6 reviews)
Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
Chicago, IL
6% off
Price is £1,486
£1,486
£212 per night
includes taxes & fees
Image gallery for Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
1010 out of 10 rating
Exceptional
(42 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
14% off
Price is £1,683
£1,683
£240 per night
includes taxes & fees
Image gallery for Family frndly TwnHm by navy base
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Family frndly TwnHm by navy base
Waukegan, IL
15% off
Price is £970
£970
£139 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(20 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
7% off
Price is £3,384
£3,384
£483 per night
includes taxes & fees
Image gallery for 3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
9.09.0 out of 10 rating
Wonderful
(9 reviews)
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Waukegan, IL
8% off
Price is £1,106
£1,106
£158 per night
includes taxes & fees
Image gallery for Trendy|Comfortable|1BR|Lincoln Square
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Trendy|Comfortable|1BR|Lincoln Square
Chicago, IL
7% off
Price is £1,800
£1,800
£257 per night
includes taxes & fees
Image gallery for Experience Chicago living near United Center
9.29.2 out of 10 rating
Wonderful
(26 reviews)
Experience Chicago living near United Center
Chicago, IL
13% off
Price is £913
£913
£130 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, IL
7% off
Price is £3,423
£3,423
£489 per night
includes taxes & fees
Image gallery for Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Chicago, IL
7% off
Price is £1,004
£1,004
£143 per night
includes taxes & fees
Image gallery for Stylish Corner 2BR in the Loop | City & Lake Views
9.69.6 out of 10 rating
Exceptional
(58 reviews)
Stylish Corner 2BR in the Loop | City & Lake Views
Chicago, IL
7% off
Price is £2,440
£2,440
£349 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR in the Loop | City Views
9.09.0 out of 10 rating
Wonderful
(24 reviews)
Spectacular Corner 3BR in the Loop | City Views
Chicago, IL
7% off
Price is £3,507
£3,507
£501 per night
includes taxes & fees
Image gallery for Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
1010 out of 10 rating
Exceptional
(23 reviews)
Re-imagined 1880's cottage walking distance to Highwood, Metra, Lake Michigan
Chicago (and vicinity), IL
12% off
Price is £1,661
£1,661
£237 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Winnetka Station
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
Sleeps 18 · 8 bedrooms · 3 bathrooms
2.02.0 out of 10
1 review(1 review)
6 Kings Ping-Pong Gazebo!
Sleeps 16 · 5 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Minutes from Naval Base & Six Flags
Sleeps 3 · 1 bedroom · 1 bathroom
8.48.4 out of 10
Very goodvery good
5 reviews(5 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value