Holiday rentals near Water Tower Place
We found 3,038 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:24 Oct - 31 Oct
Image gallery for Gorgeous N. Kenwood/Hyde Park
8.08.0 out of 10 rating
Very good
(7 reviews)
Gorgeous N. Kenwood/Hyde Park
Chicago, IL
7% off
Price is AU$4,500
AU$4,500
AU$643 per night
includes taxes & fees
Image gallery for Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
Chicago, IL
7% off
Price is AU$8,542
AU$8,542
AU$1,220 per night
includes taxes & fees
Image gallery for Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Unique And Amazing Gigantic Sunlit Loft ~ One Of A Kind ~ Excellent Location!
Chicago, IL
8% off
Price is AU$19,496
AU$19,496
AU$2,785 per night
includes taxes & fees
Image gallery for Cozy 2 Bedroom 1 Bath. Centrally located with shared porch
8.48.4 out of 10 rating
Very good
(8 reviews)
Cozy 2 Bedroom 1 Bath. Centrally located with shared porch
Chicago, IL
7% off
Price is AU$1,585
AU$1,585
AU$226 per night
includes taxes & fees
Image gallery for Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
1010 out of 10 rating
Exceptional
(6 reviews)
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
Chicago, IL
19% off
Price is AU$5,032
AU$5,032
AU$719 per night
includes taxes & fees
Image gallery for Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
8.88.8 out of 10 rating
Excellent
(19 reviews)
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
Chicago, IL
7% off
Price is AU$2,252
AU$2,252
AU$322 per night
includes taxes & fees
Image gallery for Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field
1010 out of 10 rating
Exceptional
(43 reviews)
Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field
Chicago, IL
7% off
Price is AU$3,779
AU$3,779
AU$540 per night
includes taxes & fees
Image gallery for Chic and Spacious Bi-level 3BD in Bucktown!
1010 out of 10 rating
Exceptional
(6 reviews)
Chic and Spacious Bi-level 3BD in Bucktown!
Chicago, IL
7% off
Price is AU$4,384
AU$4,384
AU$626 per night
includes taxes & fees
Image gallery for Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Chicago, IL
13% off
Price is AU$14,161
AU$14,161
AU$2,023 per night
includes taxes & fees
Image gallery for Enjoy Chicago/suburbs 2BR townhouse fully equipped
1010 out of 10 rating
Exceptional
(5 reviews)
Enjoy Chicago/suburbs 2BR townhouse fully equipped
Chicago, IL
7% off
Price is AU$2,955
AU$2,955
AU$422 per night
includes taxes & fees
Image gallery for Finished Basement in Historic Oak Park with 2 cats
8.48.4 out of 10 rating
Very good
(5 reviews)
Finished Basement in Historic Oak Park with 2 cats
Oak Park, IL
9% off
Price is AU$1,299
AU$1,299
AU$186 per night
includes taxes & fees
Image gallery for Steps from the “L” train to Wrigley & Downtown
1010 out of 10 rating
Exceptional
(48 reviews)
Steps from the “L” train to Wrigley & Downtown
Chicago, IL
7% off
Price is AU$4,638
AU$4,638
AU$663 per night
includes taxes & fees
Image gallery for Entire 2 bedroom with Office & Deck!
9.29.2 out of 10 rating
Wonderful
(11 reviews)
Entire 2 bedroom with Office & Deck!
Chicago, IL
10% off
Price is AU$2,254
AU$2,254
AU$322 per night
includes taxes & fees
Image gallery for Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood
9.49.4 out of 10 rating
Exceptional
(41 reviews)
Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood
Chicago, IL
7% off
Price is AU$4,283
AU$4,283
AU$612 per night
includes taxes & fees
Image gallery for A home away from home! <No events allowed>
9.69.6 out of 10 rating
Exceptional
(122 reviews)
A home away from home! <No events allowed>
Chicago, IL
7% off
Price is AU$4,242
AU$4,242
AU$606 per night
includes taxes & fees
Image gallery for Stunning New 6 Bedroom Home w/ Parking in Chicago (Superhosts)
9.09.0 out of 10 rating
Wonderful
(18 reviews)
Stunning New 6 Bedroom Home w/ Parking in Chicago (Superhosts)
Chicago, IL
7% off
Price is AU$7,172
AU$7,172
AU$1,025 per night
includes taxes & fees
Image gallery for The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
The Hyde Park Hide-A-Way is ready to welcome you with the comfort of home!
Chicago, IL
7% off
Price is AU$2,285
AU$2,285
AU$326 per night
includes taxes & fees
Image gallery for Chicago Oasis - Near United Center & Downtown
8.48.4 out of 10 rating
Very good
(7 reviews)
Chicago Oasis - Near United Center & Downtown
Chicago, IL
7% off
Price is AU$3,632
AU$3,632
AU$519 per night
includes taxes & fees
Image gallery for Comfort/Clean!: Free Parking 15 min ORD/Downtown3
8.48.4 out of 10 rating
Very good
(18 reviews)
Comfort/Clean!: Free Parking 15 min ORD/Downtown3
Chicago, IL
20% off
Price is AU$1,197
AU$1,197
AU$171 per night
includes taxes & fees
Image gallery for Charming 2-bedroom 1 block to Wrigley
9.29.2 out of 10 rating
Wonderful
(12 reviews)
Charming 2-bedroom 1 block to Wrigley
Chicago, IL
10% off
Price is AU$3,355
AU$3,355
AU$479 per night
includes taxes & fees
Image gallery for Spacious 3-bedroom Duplex condo
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Spacious 3-bedroom Duplex condo
Chicago, IL
7% off
Price is AU$2,588
AU$2,588
AU$370 per night
includes taxes & fees
Image gallery for Great 3 bedroom rental unit near Logan Square
9.69.6 out of 10 rating
Exceptional
(48 reviews)
Great 3 bedroom rental unit near Logan Square
Chicago, IL
16% off
Price is AU$1,704
AU$1,704
AU$243 per night
includes taxes & fees
Image gallery for Skyline Duplex Penthouse w private rooftop & optional parking for up to 8 guests
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Skyline Duplex Penthouse w private rooftop & optional parking for up to 8 guests
Chicago, IL
11% off
Price is AU$6,560
AU$6,560
AU$937 per night
includes taxes & fees
Image gallery for Toca Bella ~ 7mins to Downtown
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Toca Bella ~ 7mins to Downtown
Chicago, IL
7% off
Price is AU$2,190
AU$2,190
AU$313 per night
includes taxes & fees
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Find the best place to stay - Water Tower Place
Showing deals for: 24 Oct - 27 Oct
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
451 reviews(451 reviews)
The current price is AU$1,713
AU$1,713
for 3 nights, 1 room
AU$571 per night
includes taxes & fees
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)
The current price is AU$4,834
AU$4,834
for 3 nights, 1 apartment
AU$1,611 per night
includes taxes & fees
❤️🔥MAGNIFICENT NEW Home w/8 Beds & Free Parking❤️🔥
Sleeps 17 · 4 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
The current price is AU$4,730
AU$4,730
for 3 nights, 1 home
AU$1,577 per night
includes taxes & fees
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)
The current price is AU$1,365
AU$1,365
for 3 nights, 1 home
AU$455 per night
includes taxes & fees
Cheerful 4 bedroom smart home w/ indoor fireplace
Sleeps 12 · 4 bedrooms · 3+ bathrooms
7.87.8 out of 10
Goodgood
13 reviews(13 reviews)
The current price is AU$2,511
AU$2,511
for 3 nights, 1 home
AU$837 per night
includes taxes & fees
52nd Floor MagMile Penthouse VIEWS Fireplace Pool
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
398 reviews(398 reviews)
The current price is AU$2,256
AU$2,256
for 3 nights, 1 room
AU$752 per night
includes taxes & fees
Top rated rentals - Water Tower Place
Good location plenty of room
1010 out of 10
Exceptionalexceptional
125 reviews(125 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