Cumberland Station holiday rentals
We found 3,740 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
8% off
Price is AU$12,638
AU$12,638
AU$1,805 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 AU$13,469
AU$13,469
AU$1,924 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 AU$10,731
AU$10,731
AU$1,533 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 AU$2,898
AU$2,898
AU$414 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 AU$10,857
AU$10,857
AU$1,551 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 AU$3,535
AU$3,535
AU$505 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 AU$7,963
AU$7,963
AU$1,138 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 AU$7,869
AU$7,869
AU$1,124 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 AU$8,607
AU$8,607
AU$1,230 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 AU$7,070
AU$7,070
AU$1,010 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 AU$5,638
AU$5,638
AU$805 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 AU$10,428
AU$10,428
AU$1,490 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 AU$6,536
AU$6,536
AU$934 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 AU$5,922
AU$5,922
AU$846 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 AU$6,607
AU$6,607
AU$944 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 AU$2,898
AU$2,898
AU$414 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 AU$3,484
AU$3,484
AU$498 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 AU$7,963
AU$7,963
AU$1,138 per night
includes taxes & fees
Image gallery for Kasa | Inviting 1 BD + Game Room Access | Chicago
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Kasa | Inviting 1 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is AU$4,537
AU$4,537
AU$648 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 AU$5,829
AU$5,829
AU$833 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
8% off
Price is AU$12,372
AU$12,372
AU$1,767 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 AU$6,648
AU$6,648
AU$950 per night
includes taxes & fees
Image gallery for #1515 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(23 reviews)
#1515 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is AU$3,535
AU$3,535
AU$505 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 AU$7,963
AU$7,963
AU$1,138 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 AU$732
AU$732
for 3 nights, 1 home
AU$244 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 AU$510
AU$510
for 3 nights, 1 home
AU$170 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 AU$1,538
AU$1,538
for 3 nights, 1 apartment
AU$513 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 AU$2,307
AU$2,307
for 3 nights, 1 home
AU$769 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 AU$2,010
AU$2,010
for 3 nights, 1 home
AU$670 per night
includes taxes & fees
Dubois Guest House Room 102
Sleeps 2 · 1 bedroom · 1 bathroom
The current price is AU$1,240
AU$1,240
for 3 nights, 1 room
AU$413 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