Cumberland Station holiday homes
We found 3,752 holiday rentals — enter your dates for availability
If you are looking to stay near Cumberland Station, scroll through and discover holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll have the amenities that you expect and more, which might include air conditioning and a pool. No matter what 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 - Cumberland Station
Showing deals for:12 Sept - 19 Sept
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$13,976
NZ$13,976
NZ$1,997 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$14,866
NZ$14,866
NZ$2,124 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
1010 out of 10 rating
Exceptional
(27 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
11% off
Price is NZ$11,504
NZ$11,504
NZ$1,643 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
9.69.6 out of 10 rating
Exceptional
(38 reviews)
Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
Chicago, IL
7% off
Price is NZ$11,608
NZ$11,608
NZ$1,658 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$3,132
NZ$3,132
NZ$447 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(16 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,826
NZ$3,826
NZ$547 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Game Room Access | Chicago
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Kasa | Family Friendly 3 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is NZ$8,761
NZ$8,761
NZ$1,252 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$8,558
NZ$8,558
NZ$1,223 per night
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(29 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, Illinois
7% off
Price is NZ$9,454
NZ$9,454
NZ$1,351 per night
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
1010 out of 10 rating
Exceptional
(9 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, Illinois
8% off
Price is NZ$7,589
NZ$7,589
NZ$1,084 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$6,070
NZ$6,070
NZ$867 per night
includes taxes & fees
Image gallery for Luxury Designer Penthouse North - Pool - Gold Coast
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Luxury Designer Penthouse North - Pool - Gold Coast
Chicago, Illinois
8% off
Price is NZ$11,126
NZ$11,126
NZ$1,589 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
(51 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
7% off
Price is NZ$7,064
NZ$7,064
NZ$1,009 per night
includes taxes & fees
Image gallery for 2BR Designer Loft: Modern Luxe in City Center
1010 out of 10 rating
Exceptional
(6 reviews)
2BR Designer Loft: Modern Luxe in City Center
Chicago, Illinois
7% off
Price is NZ$6,411
NZ$6,411
NZ$916 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$7,097
NZ$7,097
NZ$1,014 per night
includes taxes & fees
Image gallery for #1514 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(10 reviews)
#1514 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,132
NZ$3,132
NZ$447 per night
includes taxes & fees
Image gallery for Kasa | Relaxing Studio + Pet Friendly | Chicago
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Kasa | Relaxing Studio + Pet Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$3,771
NZ$3,771
NZ$539 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$8,761
NZ$8,761
NZ$1,252 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 902 - Terrace - River North
8.88.8 out of 10 rating
Excellent
(5 reviews)
Luxury Loft Collection 902 - Terrace - River North
Chicago, Illinois
7% off
Price is NZ$13,693
NZ$13,693
NZ$1,956 per night
includes taxes & fees
Image gallery for Unbeatable Top Floor: Views, Central, Modern
1010 out of 10 rating
Exceptional
(5 reviews)
Unbeatable Top Floor: Views, Central, Modern
Chicago, IL
8% off
Price is NZ$6,346
NZ$6,346
NZ$907 per night
includes taxes & fees
Image gallery for 2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
8.08.0 out of 10 rating
Very good
(13 reviews)
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
Chicago, IL
11% off
Price is NZ$7,075
NZ$7,075
NZ$1,011 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Kasa | Family Friendly 3 BD + Pet Friendly | Chicago
Chicago, Illinois
8% off
Price is NZ$8,761
NZ$8,761
NZ$1,252 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,826
NZ$3,826
NZ$547 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is NZ$3,493
NZ$3,493
NZ$499 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Cumberland Station
Showing deals for: 11 Sept - 14 Sept
Less is more! Pet friendly Tiny Home near Chicago!
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
The current price is NZ$775
NZ$775
for 3 nights, 1 home
NZ$258 per night
includes taxes & fees
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "
Sleeps 4 · 25 bedrooms · 1 bathroom
6.86.8 out of 10
3 reviews(3 reviews)
The current price is NZ$719
NZ$719
for 3 nights, 1 home
NZ$240 per night
includes taxes & fees
Modern & Spacious Stay in Historic Bronzeville
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
The current price is NZ$1,666
NZ$1,666
for 3 nights, 1 apartment
NZ$555 per night
includes taxes & fees
Private Patio & BBQ - Fireplace | LCP Collection
Sleeps 8 · 3 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
2 reviews(2 reviews)
The current price is NZ$2,509
NZ$2,509
for 3 nights, 1 home
NZ$836 per night
includes taxes & fees
Modern Farmhouse | Yard + Pets OK | LCP Collection
Sleeps 6 · 3 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
The current price is NZ$2,108
NZ$2,108
for 3 nights, 1 home
NZ$703 per night
includes taxes & fees
Dubois Guest House Room 102
Sleeps 2 · 1 bedroom · 1 bathroom
The current price is NZ$1,327
NZ$1,327
for 3 nights, 1 room
NZ$442 per night
includes taxes & fees
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