Holiday rentals near The Glen Club
We found 3,361 holiday rentals — enter your dates for availability
Choose the perfect holiday home within easy reach of The Glen Club. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - The Glen Club
Showing deals for:3 Oct - 10 Oct
Image gallery for Beautiful Downtown 3BR with Free Parking
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Beautiful Downtown 3BR with Free Parking
Chicago, IL
7% off
Price is NZ$9,220
NZ$9,220
NZ$1,317 per night
includes taxes & fees
Image gallery for Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
9.89.8 out of 10 rating
Exceptional
(30 reviews)
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie, IL
9% off
Price is NZ$7,705
NZ$7,705
NZ$1,101 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(12 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, Illinois
7% off
Price is NZ$14,512
NZ$14,512
NZ$2,073 per night
includes taxes & fees
Image gallery for Cozy, Comfortable and Convenient apartment. Close to everything!
9.89.8 out of 10 rating
Exceptional
(65 reviews)
Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park, IL
8% off
Price is NZ$3,020
NZ$3,020
NZ$431 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(8 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$9,013
NZ$9,013
NZ$1,288 per night
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(39 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$6,997
NZ$6,997
NZ$1,000 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, Illinois
7% off
Price is NZ$2,847
NZ$2,847
NZ$407 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
1010 out of 10 rating
Exceptional
(10 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, Illinois
8% off
Price is NZ$6,672
NZ$6,672
NZ$953 per night
includes taxes & fees
Image gallery for Family frndly TwnHm by navy base
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Family frndly TwnHm by navy base
Waukegan, IL
12% off
Price is NZ$2,176
NZ$2,176
NZ$311 per night
includes taxes & fees
Image gallery for Luxury Designer Penthouse South | Pool | Gold Coast
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Luxury Designer Penthouse South | Pool | Gold Coast
Chicago, Illinois
7% off
Price is NZ$12,849
NZ$12,849
NZ$1,836 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
(38 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
7% off
Price is NZ$4,072
NZ$4,072
NZ$582 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 03 - Terrace - River North
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Luxury Loft Collection 03 - Terrace - River North
Chicago, IL
8% off
Price is NZ$15,383
NZ$15,383
NZ$2,198 per night
includes taxes & fees
Image gallery for Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
1010 out of 10 rating
Exceptional
(16 reviews)
Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
Chicago, IL
7% off
Price is NZ$11,440
NZ$11,440
NZ$1,634 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
(54 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is NZ$6,670
NZ$6,670
NZ$953 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(14 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
7% off
Price is NZ$12,960
NZ$12,960
NZ$1,851 per night
includes taxes & fees
Image gallery for Beautiful Unit CHI in Prime River North - 1
9.09.0 out of 10 rating
Wonderful
(13 reviews)
Beautiful Unit CHI in Prime River North - 1
Chicago, Illinois
15% off
Price is NZ$6,374
NZ$6,374
NZ$911 per night
includes taxes & fees
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field
9.49.4 out of 10 rating
Exceptional
(27 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
8% off
Price is NZ$3,223
NZ$3,223
NZ$460 per night
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
9.49.4 out of 10 rating
Exceptional
(26 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,696
NZ$6,696
NZ$957 per night
includes taxes & fees
Image gallery for Spacious 5 BR / King Size Beds + Private Parking!
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Spacious 5 BR / King Size Beds + Private Parking!
Chicago, IL
8% off
Price is NZ$9,762
NZ$9,762
NZ$1,395 per night
includes taxes & fees
Image gallery for Splendid Corner 3BR in the Loop | City Views
9.49.4 out of 10 rating
Exceptional
(14 reviews)
Splendid Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$8,011
NZ$8,011
NZ$1,144 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 NZ$10,555
NZ$10,555
NZ$1,508 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,982
NZ$3,982
NZ$569 per night
includes taxes & fees
Image gallery for Charming 3-bedroom apartment with AC and WiFi in Waukegan.
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Charming 3-bedroom apartment with AC and WiFi in Waukegan.
Waukegan, IL
8% off
Price is NZ$2,534
NZ$2,534
NZ$362 per night
includes taxes & fees
Image gallery for Spacious 3 bedroom in ideal Roscoe village location
1010 out of 10 rating
Exceptional
(45 reviews)
Spacious 3 bedroom in ideal Roscoe village location
Chicago, IL
7% off
Price is NZ$3,228
NZ$3,228
NZ$461 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - The Glen Club
1BR Gem by Shops & Dining
Sleeps 2 · 1 bedroom · 1 bathroom
Charming 2-bedroom residence in Jefferson Park, Chicago!
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
King Bed | Smart TV | Historic Location
Sleeps 13 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
Wrigleyville Suites
Sleeps 22 · 9 bedrooms
9.29.2 out of 10
Wonderfulwonderful
7 reviews(7 reviews)
The Gem Museum Suites
Sleeps 5 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
69 reviews(69 reviews)
Contemporary house with partial lake views/quiet and private area/gut reno/2023
Sleeps 8 · 4 bedrooms · 4+ bathrooms
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