Riverside Holiday Rentals

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Check prices for these dates

Tonight
31 Dec - 1 Jan
Tomorrow
1 Jan - 2 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Riverside holiday rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1028)
"My favorite place to stay hands-down"
United States
Michele
The price is HK$853
HK$1,230 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sentral Michigan Avenue
Front of property
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
The price is HK$1,023
HK$1,201 total
includes taxes & fees
5 Jan - 6 Jan 2026
Chicago luxury home suites
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (17)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is HK$536
HK$1,481 total
includes taxes & fees
5 Jan - 6 Jan 2026
Twice as Nice: Chic 2BR Stay with Style & Space
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$490
HK$1,310 total
includes taxes & fees
1 Jan - 2 Jan 2026
1BR Modern Luxe Apt with In-Unit Laundry
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Stylish 1BR in West Loop
Downtown Chicago
10.0 out of 10, Exceptional, (10)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$490
HK$1,310 total
includes taxes & fees
5 Jan - 6 Jan 2026
Stylish 1BR in West Loop
Interior
Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit

Gold Coast Living: Modern Studio Unit
Downtown Chicago
10.0 out of 10, Exceptional, (5)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is HK$536
HK$1,287 total
includes taxes & fees
5 Jan - 6 Jan 2026
Gold Coast Living: Modern Studio Unit
Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (6)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is HK$490
HK$1,310 total
includes taxes & fees
5 Jan - 6 Jan 2026
West Loop Living – Bright 1BR
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$490
HK$1,310 total
includes taxes & fees
5 Jan - 6 Jan 2026
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very good, (5)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is HK$490
HK$1,310 total
includes taxes & fees
15 Jan - 16 Jan 2026
The One: A 1BR Stay That Feels Like Home
Interior
River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$777
HK$2,442 total
includes taxes & fees
5 Jan - 6 Jan 2026
River North Rooftop With In and Out Parking 3
Business centre
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Private kitchen
ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
Near North Side
9.8 out of 10, Exceptional, (9)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
The price is HK$6,969
HK$9,814 total
includes taxes & fees
5 Jan - 6 Jan 2026
ENVITAE Hotel 4 Bedroom Luxury Apartments
Outdoor dining
3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
2.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (20)
"The apartment was clean and in an easily accessible location just a short walk to public transport. We stayed three nights on a business trip and would definitely stay again. "
United States
Ryan S.
The price is HK$2,091
HK$4,845 total
includes taxes & fees
3 Jan - 4 Jan 2026
3BR Luxury Suite w/Gym and Balcony
Front of property – evening/night
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (407)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is HK$490
HK$1,311 total
includes taxes & fees
7 Jan - 8 Jan 2026
Sleek 1BR Apt w/ Laundry
TV, offices
Complete 1BR Home Sum

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is HK$490
HK$1,310 total
includes taxes & fees
1 Jan - 2 Jan 2026
Complete 1BR Home Sum
Iron/ironing board, travel cot, WiFi, bed sheets
Modern Studio Near UChicago

Modern Studio Near UChicago

Modern Studio Near UChicago
Hyde Park
9.6 out of 10, Exceptional, (11)
"Clean room and convenient location! "
United States
Gabriela
The price is HK$443
HK$1,177 total
includes taxes & fees
5 Jan - 6 Jan 2026
Modern Studio Near UChicago
Terrace/patio
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Uptown
9.6 out of 10, Exceptional, (14)
"The property was close to a venue I was attending, so that was convenient; however, the parking was inconvenient. The recommended parking was a ten minute walk. The deposit that was held was higher than a typical hotel reservation and that was on top of the fees and rules that were provided for the overnight stay. Which is fine, if the room was exceptional, which it was not. The furnishings were the most inexpensive that could be purchased and at the end of its use. Not a comfortable stay...
United States
Janet
The price is HK$420
HK$1,910 total
includes taxes & fees
1 Jan - 2 Jan 2026
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
TV
Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.6 out of 10, Exceptional, (25)
"Great stay"
United States
Kayla K.
The price is HK$490
HK$1,310 total
includes taxes & fees
1 Jan - 2 Jan 2026
Nice 1BR Spot, Unwind & Relax
Fridge, microwave, oven, dishwasher
Cabin 308 by 747 Lofts

Cabin 308 by 747 Lofts

Cabin 308 by 747 Lofts
West Town
9.4 out of 10, Exceptional, (17)
"Beautiful space that is extremely close to the blue line subway. Very cozy apartment, clean, quiet, and in a safe area. Short subway or uber ride to get to the city and direct blue line access to the airport. Check in and check out were easy and we had no issues accessing the space with our temporary code provided. We would absolutely stay here again! "
United States
Robert M.
The price is HK$673
HK$1,741 total
includes taxes & fees
2 Jan - 3 Jan 2026
Cabin 308 by 747 Lofts
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 Riverside Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Everything! Beautiful place "
Margaret 1-night trip
Posted 7 hours ago
InterContinental Chicago Magnificent Mile by IHG

Find out more about Riverside

Search for holiday rentals in Riverside on Expedia! You can easily find your home rentals, villas, holiday apartments in Riverside using one of the methods below:

  • View our selection of featured holiday rentals in Riverside
  • Use the map to find apartments and other holiday homes in the Riverside neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Riverside while they last

Look no further and take a look at our great range of rental properties in Riverside!

Frequently asked questions

Are there holiday rentals in Riverside?

Yes, there are holiday rentals close to the most popular sights in Riverside, or you can select a more secluded option if you're looking for a relaxing stay. Riverside is known for its riverfront and zoo. Make sure you have time to check out the shopping while you're in the area.

What are some of the best holiday rentals that Riverside has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Riverside offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What’s there to see and do in Riverside?

While exploring the area, visit family-friendly sights like Galloping Ghost, or get outside and enjoy nature at Millennium Park. You’ll find favourite places to visit such as Michigan Avenue and Wrigley Field in the wider area.

What’s a holiday rental in Riverside like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Riverside. Holiday rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family trips or small group gatherings.