Jackson Station Vacation Rentals

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Browse Select Jackson Station Vacation Homes

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.8 out of 10, Exceptional, (14)
"This duplex in Old Town was very tastefully refurbished and decorated. The kitchen is outfitted with the best appliances, including an electric kettle. (Note to hosts: ALWAYS provide a tea kettle of some kind and you'll get an automatic five-star rating from me!) The house is quite roomy and comfortable and the four of us settled in nicely. It's a bit of a walk to the train, but the neighborhood is nice, so you don't mind. I highly recommend."
Walk to the Beach! Theater-Coffee Bar-Games-Gym

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (50)
"We stayed for a number of weeks at the property - it was an excellent stay! The property is exactly as advertised and the owner was extremely helpful, communicative, and responsive throughout. The house is modern, in good condition, and is an excellent location."
Luxury House in the heart of Old Town with Parking

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

9.2 out of 10, Wonderful, (17)
"Very quiet and close to CTA , Old Town easy access to the city"
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

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

10.0 out of 10, Exceptional, (90)
"Awesome location, plenty of space, timely communication, clean. We loved it!"
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

9.2 out of 10, Wonderful, (58)
"Super convenient for Old Town and train station, will stay there again."
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

9.8 out of 10, Exceptional, (99)
"Great choice for a weekend with friends in Chicago. We were relatively close to Wrigley, Second City, and the bars up and down Wells in Old Town. Plus we could easily take the L to downtown for museums and a boat tour on the river.The house had great bedrooms, beds were comfy and bathrooms were modern and well-appointed.Would stay here again if I ever had a big enough group.Host was very communicative and helped us throughout our stay with making things easier. Felt very welcome. "
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (98)
"Good for our get together."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Historic luxury townhouse on Chicago's Gold Coast

9.4 out of 10, Exceptional, (72)
"All good"
Historic luxury townhouse on Chicago's Gold Coast

2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

The price is CA $527
CA $776 total
includes taxes & fees
Sep 1 - Sep 2
2 Luxury Queen with Rooftop Lounge & City Views Near Attractions

2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago

The price is CA $358
CA $549 total
includes taxes & fees
Sep 1 - Sep 2
2 Spacious King Room with Rooftop Lounge & Scenic Views of Chicago

Beautiful, Remodeled Penthouse Unit in Old Town!

9.4 out of 10, Exceptional, (26)
"Super nice property, and the host was so helpful and kind. Super happy with the house overall, would recommend! "
Beautiful, Remodeled Penthouse Unit in Old Town!

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

Cozy Room with Rooftop Lounge & City Views in River North

10.0 out of 10, Exceptional, (1)
"The hotel was very nice and the location was excellent. Was able to walk to many locations. Noise wasn't bad for a city experience. Hotel restaurant was very good."
The price is CA $215
CA $319 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Room with Rooftop Lounge & City Views in River North

Spacious Room with Rooftop Lounge & Scenic Views of Chicago

The price is CA $227
CA $334 total
includes taxes & fees
Sep 1 - Sep 2
Spacious Room with Rooftop Lounge & Scenic Views of Chicago

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

Luxury SOHO Styled Two-Level Townhouse - Old Town

10.0 out of 10, Exceptional, (16)
"Very convenient to the EL and the zoo. Large clean space. Perfect for a family trip"
Luxury SOHO Styled Two-Level Townhouse - Old Town

GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)

9.8 out of 10, Exceptional, (23)
"My coworkers and I had a wonderful time at this perfectly located property. The property had plenty of privacy, charming At CB textural character, and was perfectly located for shopping and dining. Would definitely stay here again!"
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)

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

Clean & Modern • Central Location • Free Coffee!

Clean & Modern • Central Location • Free Coffee!

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.
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Top Jackson Station Hotel Reviews

Find out more about Jackson Station

Find out more about Jackson Station

What types of Vacation Homes can I find in Jackson Station?

When you’re looking for Jackson Station Vacation Homes in 2025, you can use Expedia’s filters to find accommodation that’s family-friendly or business-friendly, and narrow down your search results by amenities, price per night, and much more. For example, you can search for Vacation Homes that welcome pets, or one with accessibility features. You’ll find a range of places to stay to suit every budget, so if you're looking for cheap Vacation Homes in Jackson Station, use our simple search function to help you secure a good deal. If the exact location of Vacation Homes is important to you, try our map facility to view available places in relation to each other and to Jackson Station.

How much do Vacation Homes cost in Jackson Station?

Prices for Jackson Station Vacation Homes can start from as little as * in 2025. The cost per night varies depending on several factors, including the amenities on offer at Vacation Homes, the exact location of Vacation Homes and how far they are from Jackson Station, as well as how high the demand for accommodation is near Jackson Station on the dates of your booking. At Expedia, we cater for every budget, so if you’re looking for cheap Vacation Homes in Jackson Station, you can sleep easy knowing that we’ll help you to secure some of the very best deals on offer.

How to find the best deals on Jackson Station Vacation Homes?

Expedia’s search function can help you find a great deal on Jackson Station Vacation Homes. Changing the sort order of your search results can help you to find cheap Vacation Homes in Jackson Station at a glance. If you have a specific price range in mind, try selecting minimum and maximum prices per night to narrow your results. You can also filter by guest ratings and star ratings to find some of the best offers for Vacation Homes within your budget. Don’t forget, if you’re an Expedia Rewards member, you can use the ‘Member Prices’ filter to make instant savings on your booking.

Why should I choose Expedia to book Jackson Station Vacation Homes?

One of the many benefits of booking Jackson Station Vacation Homes with Expedia is the clear and simple search function. When you use the many filters on offer, you can easily compile a shortlist of fantastic places to stay, and make comparisons between the different Vacation Homes so that you can choose exactly what you need. At Expedia, it’s possible to create your own customized package and make great savings by booking flights, car hire, and more at the same time as Jackson Station Vacation Homes. And don’t forget that with free membership to Expedia Rewards, you can earn points on all eligible purchases, and build your points total to use towards future travel.

What is the cancellation policy on booking Jackson Station Vacation Homes?

It’s often possible to change or cancel bookings at Jackson Station Vacation Homes without a fee, but it depends on the rules and restrictions of the various Vacation Homes. Many booking options offer a window of flexibility, for example a full refund if you cancel more than 24 or 48 hours before Jackson Station arrival dates. It’s best to check the policies of the individual Vacation Homes before making a booking, if flexibility is important to you. You can filter for the ‘Fully refundable’ payment type when you search for Vacation Homes. You can also view the terms of the different Vacation Homes at any time by checking the details of your booking at Expedia.

*Prices and availability are subject to change. Additional terms may apply 

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