Book Holiday Homes in Montgomery

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Featured Holiday Homes in Montgomery

Clarendon Hills Top Floor

Clarendon Hills Top Floor

Clarendon Hills IL
With a stay at this vacation home in Clarendon Hills, you'll be within a 5-minute drive of Ty Warner Park and Twin Lakes Park.
Opens in a new windowClarendon Hills Top Floor
Spacious open concept home w/ game room + firepit

Spacious open concept home w/ game room + firepit

Winfield IL
With a stay at this vacation home in Winfield, you'll be within a 5-minute drive of DuPage Event Center & Fairgrounds and Cosley Zoo.
Opens in a new windowSpacious open concept home w/ game room + firepit
3-bedroom hillside property in woods with fireplace and lake view

3-bedroom hillside property in woods with fireplace and lake view

Lemont IL
The price is AU$353 per night from 5 Jan to 6 Jan
AU$353
5 Jan - 6 Jan 2026
includes taxes & fees
With a stay at this vacation home in Lemont, you'll be within a 10-minute drive of The Forge: Lemont Quarries Adventure Park and Cog Hill Golf & Country ...
Opens in a new window3-bedroom hillside property in woods with fireplace and lake view
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Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

Aurora IL
The price is AU$1,640 per night from 1 Jan to 2 Jan
AU$1,640
1 Jan - 2 Jan 2026
includes taxes & fees
When you stay at this vacation home in Aurora, you'll be within a 10-minute drive of Aurora Regional Fire Museum and Hollywood Casino Aurora.
Opens in a new windowSpacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station

Wheaton IL
The price is AU$464 per night from 29 Dec to 30 Dec
AU$464
29 Dec - 30 Dec
includes taxes & fees
With a stay at this vacation home in Wheaton, you'll be within a 5-minute drive of Wheaton College and Billy Graham Center Museum.
Opens in a new window✽ Charming Cottage ✽ close to College/Town/Station
Modern Home in Trendy Neighborhood 40 from Downtown Chicago

Modern Home in Trendy Neighborhood 40 from Downtown Chicago

Plainfield IL
Located in Shorewood, this vacation home is within a 5-minute drive of Liberty Park and Hampton Glen.
Opens in a new windowModern Home in Trendy Neighborhood 40 from Downtown Chicago
Furnished Private home in Aurora sleeps 9 guests

Furnished Private home in Aurora sleeps 9 guests

Aurora IL
Located in Aurora, this vacation home is within a 5-minute drive of Copley Memorial Hospital and Rush-Copley Medical Center.
Opens in a new windowFurnished Private home in Aurora sleeps 9 guests
"St Geneva" Private With River View! 7 min to the Q Center

"St Geneva" Private With River View! 7 min to the Q Center

St. Charles IL
When you stay at this vacation home in St. Charles, you'll be on a river, within a 15-minute walk of Beith House Museum and St. Charles Heritage Center and Camp ...
Opens in a new window"St Geneva" Private With River View! 7 min to the Q Center
Cozy 5-bedroom with lake views and spacious deck

Cozy 5-bedroom with lake views and spacious deck

Westmont IL
Located in Westmont, this vacation home is on a lake, a 3-minute drive from Ty Warner Park and 6 minutes from Oakbrook Center Mall.
Opens in a new windowCozy 5-bedroom with lake views and spacious deck
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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.

Montgomery 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 Montgomery vacation homes are the perfect way for you to wing it.

Holiday houses in Montgomery 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 Montgomery 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 Montgomery adventures, obvs.

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

Montgomery Holiday Homes essential information

Accommodation
162 Holiday Homes
Lowest Price
AU$79
Highest Price
AU$1,640
Popular accommodation
Clarendon Hills Top Floor, Spacious open concept home w/ game room + firepit, 3-bedroom hillside property in woods with fireplace and lake view, Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall. , ✽ Charming Cottage ✽ close to College/Town/Station, Modern Home in Trendy Neighborhood 40 from Downtown Chicago, Furnished Private home in Aurora sleeps 9 guests, "St Geneva" Private With River View! 7 min to the Q Center, Cozy 5-bedroom with lake views and spacious deck

Top trending hotels in Montgomery

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 28 Dec to 29 Dec
AU$119
28 Dec - 29 Dec
includes taxes & fees
Located in Lombard (Highland Hills), SureStay Plus Hotel by Best Western Chicago Lombard is within a 5-minute drive of Yorktown Shopping Center and Advocate ...
Opens in a new windowSureStay Plus Hotel by Best Western Chicago Lombard
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is AU$104 per night from 7 Jan to 8 Jan
AU$104
7 Jan - 8 Jan 2026
includes taxes & fees
Located in Westmont, Chicago Club Inn & Suites is in the suburbs, within a 10-minute drive of Oakbrook Center Mall and Yorktown Shopping Center.
Opens in a new windowChicago Club Inn & Suites
Motel 6 Naperville, IL

Motel 6 Naperville, IL

2 out of 5
1585 Naperville Wheaton Road Naperville IL
Fully refundableReserve now, pay when you stay
The price is AU$79 per night from 13 Jan to 14 Jan
AU$79
13 Jan - 14 Jan 2026
includes taxes & fees
Located in Naperville, Motel 6 Naperville, IL is within a 5-minute drive of University of Chicago Hospital and Northern Illinois University - Naperville ...
Opens in a new windowMotel 6 Naperville, IL
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The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
The price is AU$178 per night from 6 Jan to 7 Jan
AU$178
6 Jan - 7 Jan 2026
includes taxes & fees
Located in Willowbrook, The Champagne Lodge & Luxury Suites is a 4-minute drive from Willowbrook Community Park and 6 minutes from Waterfall Glen Forest ...
Opens in a new windowThe Champagne Lodge & Luxury Suites
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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.

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^Subject to availability and chosen travel dates.