Damen Station vacation rentals
We found 3,731 vacation rentals — enter your dates for availability
Select the perfect vacation home within easy reach of Damen Station. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, such as a garden and pool. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Vacation rentals with weekly discounts - Damen Station
Showing deals for:Nov 14 - Nov 21
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
10% off
Price is CA $733
CA $733
CA $7,234 total
CA $7,234 total
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
10% off
Price is CA $452
CA $452
CA $4,518 total
CA $4,518 total
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
10% off
Price is CA $449
CA $449
CA $4,583 total
CA $4,583 total
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
10% off
Price is CA $501
CA $501
CA $5,058 total
CA $5,058 total
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
10% off
Price is CA $445
CA $445
CA $4,402 total
CA $4,402 total
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(58 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, IL
10% off
Price is CA $495
CA $495
CA $4,874 total
CA $4,874 total
includes taxes & fees
Image gallery for Beautiful, Remodeled Penthouse Unit in Old Town!
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Beautiful, Remodeled Penthouse Unit in Old Town!
Chicago, IL
5% off
Price is CA $431
CA $431
CA $4,361 total
CA $4,361 total
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
10% off
Price is CA $912
CA $912
CA $8,996 total
CA $8,996 total
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
10% off
Price is CA $466
CA $466
CA $4,714 total
CA $4,714 total
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
10% off
Price is CA $231
CA $231
CA $2,692 total
CA $2,692 total
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
10% off
Price is CA $361
CA $361
CA $3,586 total
CA $3,586 total
includes taxes & fees
Image gallery for Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
1010 out of 10 rating
Exceptional
(7 reviews)
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Whiting, IN
10% off
Price is CA $198
CA $198
CA $1,731 total
CA $1,731 total
includes taxes & fees
Image gallery for Cheerful 4 bedroom smart home w/ indoor fireplace
8.08.0 out of 10 rating
Very good
(14 reviews)
Cheerful 4 bedroom smart home w/ indoor fireplace
Chicago, IL
5% off
Price is CA $400
CA $400
CA $4,379 total
CA $4,379 total
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
20% off
Price is CA $128
CA $128
CA $1,488 total
CA $1,488 total
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
10% off
Price is CA $158
CA $158
CA $1,765 total
CA $1,765 total
includes taxes & fees
Image gallery for NEW LUXURY PENTHOUSE CONDO
1010 out of 10 rating
Exceptional
(186 reviews)
NEW LUXURY PENTHOUSE CONDO
Chicago, IL
5% off
Price is CA $478
CA $478
CA $4,903 total
CA $4,903 total
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
7% off
Price is CA $304
CA $304
CA $3,158 total
CA $3,158 total
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
10% off
Price is CA $435
CA $435
CA $4,307 total
CA $4,307 total
includes taxes & fees
Image gallery for Cozy 4-bedroom house in adorable Evanston with WiFi, AC
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Cozy 4-bedroom house in adorable Evanston with WiFi, AC
Evanston, IL
10% off
Price is CA $382
CA $382
CA $3,679 total
CA $3,679 total
includes taxes & fees
Image gallery for Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Chicago, IL
10% off
Price is CA $178
CA $178
CA $1,831 total
CA $1,831 total
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
10% off
Price is CA $630
CA $630
CA $6,305 total
CA $6,305 total
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
10% off
Price is CA $646
CA $646
CA $6,458 total
CA $6,458 total
includes taxes & fees
Image gallery for 4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
9.69.6 out of 10 rating
Exceptional
(10 reviews)
4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
Chicago, IL
15% off
Price is CA $474
CA $474
CA $4,923 total
CA $4,923 total
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
10% off
Price is CA $455
CA $455
CA $4,496 total
CA $4,496 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Damen Station
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
470 reviews(470 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
338 reviews(338 reviews)
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
189 reviews(189 reviews)
Prime Location! Indoor Pool, Near Millenium Park, Shedd Aquarium, Willis Tower
Sleeps 2 · 1 bedroom · 1 bathroom
7.87.8 out of 10
Goodgood
83 reviews(83 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
876 reviews(876 reviews)
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sleeps 8 · 1 bedroom
7.87.8 out of 10
Goodgood
130 reviews(130 reviews)
Top rated rentals - Damen Station
Rooftop is perfect, great location
1010 out of 10
Exceptionalexceptional
186 reviews(186 reviews)
Spent 4 nights, we had everything we needed, plus nice extra touches. Location is central and close to some great neighborhoods. Jessica was very responsive and even accommodated an early check-in for a bit extra. Would definitely stay here again.
Alex P.
Stayed May 2024
Great place in a great neighborhood!
1010 out of 10
Exceptionalexceptional
76 reviews(76 reviews)
Very nice, spacious, top floor of a house. In a great neighborhood, seconds to the train and a huge range of places to eat and drink. Amy is an incredibly friendly and helpful host!.Would love to stay there again.
Tim H.
Stayed Jun 2023
Great place!
1010 out of 10
Exceptionalexceptional
295 reviews(295 reviews)
It was a great place to stay!!
Gordon S.
Stayed Mar 2020
Great Condo, Better Service
1010 out of 10
Exceptionalexceptional
117 reviews(117 reviews)
This property was amazing for a college buddies reunion trip. It was spacious, exactly as advertised, and had all the amenities you can ask for. The location is great and the check-in is a breeze. The host/owner, Carole, is an absolute pro and a joy to deal with.
Would definitely stay here again.
Aaron F.
Stayed Jun 2019
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, yards and more
More for lessMore space, more privacy, more amenities — more value