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 Gregg House Museum and Ty Warner 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$330 per night from 16 Feb to 17 Feb
AU$330
16 Feb - 17 Feb
includes taxes & fees
With a stay at this vacation home in Lemont, you'll be within a 10-minute drive of Oldfield Oaks Dog Park and The Forge: Lemont Quarries Adventure Park.
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$1,478 per night from 11 Feb to 12 Feb
AU$1,478
11 Feb - 12 Feb
includes taxes & fees
Located in Aurora, this vacation home is a 4-minute drive from Nue Medical Solutions and 5 minutes from Aurora Regional Fire Museum.
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$440 per night from 11 Feb to 12 Feb
AU$440
11 Feb - 12 Feb
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
4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.

4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.

Glen Ellyn IL
Located in Glen Ellyn, this vacation home is a 3-minute drive from Adventist GlenOaks Hospital and 7 minutes from Lilacia Park.
Opens in a new window4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom.
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 St. Charles Heritage Center and Camp Kane and Arcada ...
Opens in a new window"St Geneva" Private With River View! 7 min to the Q Center
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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$74
Highest Price
AU$1,478
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, 4bd house, Hot-tub, full-basement, pool table & big yard,3 full bathroom., 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

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$120 per night from 11 Feb to 12 Feb
AU$120
11 Feb - 12 Feb
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
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$186 per night from 11 Feb to 12 Feb
AU$186
11 Feb - 12 Feb
includes taxes & fees
Located in Willowbrook, The Champagne Lodge & Luxury Suites is within a 10-minute drive of Burr Ridge Village Center and Flagg Creek Golf Course.
Opens in a new windowThe Champagne Lodge & Luxury 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$74 per night from 17 Feb to 18 Feb
AU$74
17 Feb - 18 Feb
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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DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr Naperville IL
Fully refundableReserve now, pay when you stay
The price is AU$127 per night from 17 Feb to 18 Feb
AU$127
17 Feb - 18 Feb
includes taxes & fees
Located in Naperville, DoubleTree by Hilton Lisle Naperville is in the business district, a 2-minute drive from Morton Arboretum and 6 minutes from College of ...
Opens in a new windowDoubleTree by Hilton Lisle Naperville
Don't see what you're looking for?
See all available properties in Montgomery
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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.