Search Vacation Homes in Ashland Station

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Ashland Station

Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover

9.0 out of 10, Wonderful, (6)
"Very convenient to the Metra blue line, lots of bars and restaurants in the neighborhood. "
Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover

Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

10.0 out of 10, Exceptional, (90)
"We stayed at the property for a bachelorette party weekend. The house was very nice and the host was so accommodating! The coffee maker was also a big plus. Highly, highly recommend for a large group! Great stay! "
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

Charming 3-bedroom house in marvelous Ukrainian village Chicago

6.0 out of 10, (2)
"We enjoyed our stay, especially the location of the neighborhood."
Charming 3-bedroom house in marvelous Ukrainian village Chicago

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.4 out of 10, Exceptional, (13)
"The house was excellent for our family. It was definitely enough room and everything was okay for our trip. Neighborhood was nice and no one bothered us. "
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

10.0 out of 10, Exceptional, (2)
"We had a great stay! Inna provided us all the info we needed to check in smoothly when we arrived and the garage spot made it easy for us to park and unload luggage straight into the house. Everything was super clean! The house is big enough that even with so many guests everyone felt spread out and had their own space. We were able to take a 5ish min walk to the beach which was such a bonus! "
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE

9.8 out of 10, Exceptional, (19)
"Beautifully maintained property in residential neighborhood proximate to fantastic food and beverage / public transportation and quick cab ride from all major Chicago attractions. "
EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE

MODERN DOWNTOWN 5-LEVEL-HOME WITH ROOFTOP AND 360-DEGREES SKYLINE VIEWS

8.6 out of 10, Excellent, (7)
"For friends traveling to Chicago this is the perfect layout for privacy, modern amenities and a wonderful place to relax. Highly recommend for its location and accommodation."
MODERN DOWNTOWN 5-LEVEL-HOME WITH ROOFTOP AND 360-DEGREES SKYLINE VIEWS

Spacious 4-Level/4-Bedroom Townhouse in West Loop

10.0 out of 10, Exceptional, (57)
"Excellent property, excellent location, excellent host!"
Spacious 4-Level/4-Bedroom Townhouse in West Loop

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

10.0 out of 10, Exceptional, (2)
"Spacious and clean property in a great location. "
Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Secure, Quiet, Solo Traveler's Fave, Free Coffee!

Secure, Quiet, Solo Traveler's Fave, Free Coffee!

Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly

10.0 out of 10, Exceptional, (3)
"Charming home in the Old Town area. Close to so many great restaurants and bars. Very spacious and clean. Our host Inna was so welcoming and helpful with recommendations!"
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (6)
"Upscale tri level home, easy location to get to and Uber from. House is very well designed and set up for a larger family group. 4 nice bedrooms with really nice bathrooms and a small workout area. Living room and kitchen open up to a back deck area with lower level sitting spaces. Great place to stay for concerts or just an easy location to visit the pier or soldier field or Wrigley or white Sox. We enjoyed our week. "
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

The Neighborhood Hotel - Little Italy One Bedroom

9.6 out of 10, Exceptional, (4)
"I would quickly recommend this listing to any friend of mine- it was a highlight of the vacation! The location is a bit outside of the heart of downtown, but is easily accessible by a 30-40 min safe walk. Clean, stylish, safe, and very comfortable. Thanks for a great stay!"
The Neighborhood Hotel - Little Italy One Bedroom

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

9.2 out of 10, Wonderful, (48)
"The space was as promised. Well furnished, clean, and comfortable. "
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

Beautiful Designer Townhome ~ Amazing Location! River West - 4-Bedroom / Unit 1

10.0 out of 10, Exceptional, (30)
"Such a great place!!!! Would 100% stay her again!"
Beautiful Designer Townhome ~ Amazing Location! River West - 4-Bedroom / Unit 1

Charming & Comfy Gem ~ 10 Mins to Downtown ~Patio!

9.0 out of 10, Wonderful, (8)
"We had a great stay! This was an awesome spot for a large group to stay near downtown Chicago!"
Charming & Comfy Gem ~ 10 Mins to Downtown ~Patio!

Secure, Private, Free Wi-Fi and Coffee, Accessible

Secure, Private, Free Wi-Fi and Coffee, Accessible

Downtown Goose Island with access to patio - 1

9.2 out of 10, Wonderful, (5)
"Tuvimos una estancia muy buena en este departamento. Está muy cerca de las principales atracciones de Chicago y tiene acceso inmediato a la vía express que recorre toda la ciudad. Muy apto para ir y regresar al aeropuerto O’Hare. Sus instalaciones fueron confortables y limpias y las indicaciones de los servicios fueron muy buenas y sencillas. Sin duda regresaríamos para aprovechar más el verano e invierno. *****"
Downtown Goose Island with access to patio - 1

2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

The price is SAR 1,620
SAR 2,338 total
includes taxes & fees
27 Jul - 28 Jul
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

Chic ART+1700sqf +3BR Home360° Roof+HotTub+CarGarage+12Guests

10.0 out of 10, Exceptional, (1)
Chic ART+1700sqf +3BR Home360° Roof+HotTub+CarGarage+12Guests
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in