Holiday rentals near Water Tower Place
We found 3,030 holiday rentals — enter your dates for availability
Choose the right private holiday rental within easy reach of Water Tower Place. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as air conditioning and cable TV. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Water Tower Place
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
13% off
Price is S$2,397
S$2,397
S$342 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
21% off
Price is S$28,426
S$28,426
S$4,061 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 S$6,609
S$6,609
S$944 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 S$4,187
S$4,187
S$598 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 S$1,567
S$1,567
S$224 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 S$4,174
S$4,174
S$596 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 S$4,069
S$4,069
S$581 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 S$4,508
S$4,508
S$644 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 S$4,651
S$4,651
S$664 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 S$8,366
S$8,366
S$1,195 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 S$3,325
S$3,325
S$475 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 S$1,348
S$1,348
S$193 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 S$2,503
S$2,503
S$358 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 S$2,864
S$2,864
S$409 per night
includes taxes & fees
Image gallery for Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
Oak Park, IL
6% off
Price is S$1,385
S$1,385
S$198 per night
includes taxes & fees
Image gallery for Historic 1920s Private Bungalow Near Logan Square!
9.89.8 out of 10 rating
Exceptional
(39 reviews)
Historic 1920s Private Bungalow Near Logan Square!
Chicago, IL
7% off
Price is S$4,368
S$4,368
S$624 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 S$5,773
S$5,773
S$825 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 S$5,917
S$5,917
S$845 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 S$4,160
S$4,160
S$594 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 S$3,068
S$3,068
S$438 per night
includes taxes & fees
Image gallery for 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
1010 out of 10 rating
Exceptional
(62 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Chicago, IL
7% off
Price is S$3,992
S$3,992
S$570 per night
includes taxes & fees
Image gallery for Stunning 3BR Penthouse in the Loop | Roof Deck
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Stunning 3BR Penthouse in the Loop | Roof Deck
Chicago, IL
7% off
Price is S$6,004
S$6,004
S$858 per night
includes taxes & fees
Image gallery for 3BR Prime Hyde Park Location Near University of Chicago and Dining
1010 out of 10 rating
Exceptional
(7 reviews)
3BR Prime Hyde Park Location Near University of Chicago and Dining
Chicago, IL
5% off
Price is S$3,067
S$3,067
S$438 per night
includes taxes & fees
Image gallery for Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Luxury Hyde Park Haven- Perfect for families and digital nomads. Pet Friendly.
Chicago, IL
14% off
Price is S$5,639
S$5,639
S$806 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Water Tower Place
Map Attractions
Find the best place to stay - Water Tower Place
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
465 reviews(465 reviews)
Stylish River North Suites: Luxury Living Near Chicago’s Best Shopping&Nightlife
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
5 reviews(5 reviews)
❤️🔥MAGNIFICENT NEW Home w/8 Beds & Free Parking❤️🔥
Sleeps 17 · 4 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
35 reviews(35 reviews)
The Chicago Hotel Collection Magnificent Mile Sleek Standard Double Queen
Sleeps 4 · 1 bedroom · 1 bathroom
8.08.0 out of 10
Very goodvery good
2 reviews(2 reviews)
Cheerful 4 bedroom smart home w/ indoor fireplace
Sleeps 12 · 4 bedrooms · 3+ bathrooms
8.08.0 out of 10
Very goodvery good
14 reviews(14 reviews)
52nd Floor MagMile Penthouse VIEWS Fireplace Pool
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
398 reviews(398 reviews)
Top rated rentals - Water Tower Place
Great for bonding, cute neighbourhood
1010 out of 10
Exceptionalexceptional
186 reviews(186 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, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value