
Holiday houses in Montgomery
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Top-rated holiday rentals in Montgomery
Guests agree: these stays are highly rated for location, cleanliness and more.

Spacious family friendly home away from home
This spacious suburban home offers 2 bedrooms with 2.5 bathrooms and a loft with a dedicated workspace. Front living room also has a sleeper couch. There is a full kitchen for your daily meals. The property can host up to 8 people, making it a great option for families. Ample parking space with a 2 car garage. Bring the whole family to this great place with lots of room for fun; additionally there is park close by for the kids. Close to shopping options, outlet malls, restaurants and casino.

5 bdrm 7 bed 2.5 bth Ranch w Fenced Yard Sleeps 10
Escape with your family at this tranquil retreat, nestled in the heart of Montgomery near highways 34 and 25. Situated on a quiet street, this spacious home boasts five bedrooms, ensuring ample space for everyone. The master bedroom features a queen-size bed and en-suite bathroom, other bedrooms offer: queen bed, full-size bed, twin bed with twin bed trundle, and the last bedroom offers a bunk bed. The property also has a fenced yard with a patio, ideal for outdoor entertaining & relaxation.

Nice, Private Ranch Home
Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

Penthouse In The Historic Hobbs
Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

“The remote retreat”
We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

1 Bed w/ Full Kitchen A Mile From Downtown Oswego
Enjoy a stay within walking distance of 3 parks and about a mile from downtown Oswego and its quaint shopping area. Nestled in the middle of a great neighborhood, you'll feel safe and be able to enjoy a quick getaway or an extended stay. If you're interested in visiting Chicago, we're close enough for day trips to the city (about 45 miles) but far enough to save some money. You'll definitely have a great time here!

Modern Boho house in Lombard 7 min to Metra
Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!

Cozy Lakeview Studio with Private Access
Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

Cozy Private Apartment Near Fox River & Downtown!
Great one bedroom apartment with queen sized bed in Aurora , IL. 10 mins away from Metra train that will take you anywhere you want to go downtown Chicago and its surrounding neighborhoods. Look forward to having an amazing & stress free stay with us. Guests often say our space "feels like home." We're proud of that tradition! See you soon,

Kaleidoscope: 4 BR, 2BA
Welcome to Kaleidoscope! Our beautifully updated four-bedroom, two-bathroom Airbnb offers a stylish and comfortable stay for families, groups, and travelers. Designed with an open-concept layout, the home features a spacious living room, dining area, cozy seating area, and a fully updated kitchen—all with brand-new, chic furnishings.

Aurora Apt with garage, fast wi-fi and laundry
This home has everything you need, 4k smart TV, 1 car garage, yard, laundry inside unit, full kitchen, comfortable king size bed and a sofa bed. There is also high speed internet available, you will feel like you're right at home.

Loft in Aurora
Enjoy a stylish experience at this centrally-located studio apartment located in the heart of downtown Aurora! Cozy, exposed brick, exposed duct work, a spiral staircase, outdoor decks on both levels and LOTS of natural light!
Popular amenities for Montgomery holiday rentals
Stay near Montgomery's top sights
Other great holiday rentals in Montgomery

“The Warrenville Grove”

Luxury Meets Cozy

Spacious 4 Beds w/ Yard – Near Naperville, Chicago

Spacious 4BR Tudor with Patio near Downtown

Little Rock Woods Retreat

Feathers Home, Cozy, King Bed, WiFi, Smart TV

Beautiful Basement Studio w/ Kitchen by Fox River

Quiet area/Petfriendly/Wi-fi/5 beds/1.5 bath
Destinations to explore
- Chicago Holiday rentals
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- Downtown Chicago Holiday rentals
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- Wrigley Field
- Soldier Field
- United Center
- Lincoln Park
- Grant Park
- Navy Pier
- Millennium Park
- Naval Station Great Lakes
- 875 North Michigan Avenue
- Six Flags Great America
- Chicago River Walk
- The Field Museum
- University of Chicago
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Donald E Stephens Convention Center
- Union Park
- Matthiessen State Park
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Byline Bank Aragon Ballroom





