Book Holiday Homes in Riverdale

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Featured Holiday Homes in Riverdale

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Chicago
Located in Chicago (Humboldt Park), this vacation home is within a 10-minute drive of Michigan Avenue and Wrigley Field.
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

Chicago
With a stay at this vacation home in Chicago (Humboldt Park), you'll be a 5-minute drive from United Center and 8 minutes from Chicago Riverwalk.
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Spacious 5-bedroom house with movie room, game room and more!

Spacious 5-bedroom house with movie room, game room and more!

Berwyn
Located in Berwyn, this vacation home is within a 15-minute drive of Millennium Park and United Center.
Spacious 5-bedroom house with movie room, game room and more!
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Elegant 4 br Old Town Home;  Private Yard; Parking; Amazing Location

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

Chicago
With a stay at this vacation home, you'll be centrally located in Chicago, within a 5-minute drive of Michigan Avenue and Chicago Riverwalk.
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Nestled just behind Marquette Park. 5 minute walk to beach.

Nestled just behind Marquette Park. 5 minute walk to beach.

Gary
With a stay at this vacation home, you'll be centrally located in Gary, within a 5-minute drive of Lake Michigan and Indiana Dunes National Park.
Nestled just behind Marquette Park. 5 minute walk to beach.
Woodlawn Oasis...10 Minutes to Dining & Downtown

Woodlawn Oasis...10 Minutes to Dining & Downtown

Chicago
With a stay at this vacation home, you'll be centrally located in Chicago, within a 5-minute drive of University of Chicago and Chicago Museum of Science and ...
Woodlawn Oasis...10 Minutes to Dining & Downtown
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

Chicago
With a stay at LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins in Chicago (Bronzeville), you'll be within a 5-minute drive of ...
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins
 LakeHouse

LakeHouse

Chicago
A stay at this vacation home places you in the heart of Chicago, just a 3-minute walk from Lake Michigan and within a 5-minute drive of Chicago Museum of Science ...
LakeHouse
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Miller Beach
With a stay at this vacation home in Gary (Miller Beach), you'll be within a 5-minute drive of Indiana Dunes National Park and Lake Michigan.
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park
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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.

Riverdale Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Riverdale vacation homes are the perfect way for you to wing it.

Holiday houses in Riverdale let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Riverdale in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Riverdale adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Riverdale with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Riverdale vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Riverdale Holiday Homes essential information

Accommodation
390 Holiday Homes
Lowest Price
AU$175
Highest Price
AU$309
Popular accommodation
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow, Spacious 5-bedroom house with movie room, game room and more!, Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location, Nestled just behind Marquette Park. 5 minute walk to beach., Woodlawn Oasis...10 Minutes to Dining & Downtown, LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins, LakeHouse, Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Top trending hotels in Riverdale

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 24 Dec to 25 Dec
AU$196
includes taxes & fees
24 Dec - 25 Dec
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 22 Jan to 23 Jan
AU$175
includes taxes & fees
22 Jan - 23 Jan 2025
With a stay at River Hotel, you'll be centrally located in Chicago, steps from Michigan Avenue and 5 minutes by foot from Chicago Riverwalk.
River Hotel
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$309 per night from 10 Jan to 11 Jan
AU$309
includes taxes & fees
10 Jan - 11 Jan 2025
Hyatt Regency Chicago is centrally located in Chicago, a 4-minute walk from Chicago Riverwalk and 7 minutes by foot from Michigan Avenue Bridge.
Hyatt Regency Chicago
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Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is AU$208 per night from 7 Jan to 8 Jan
AU$208
includes taxes & fees
7 Jan - 8 Jan 2025
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel is centrally located in Chicago, a 3-minute walk from Merchandise Mart and 14 minutes by foot from Chicago ...
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Don't see what you're looking for?
See all available properties in Riverdale
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.