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.

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Guest favourite
A bright living area features a comfortable sofa arranged around a modern coffee table. A work desk is positioned near the window, with natural light spilling in. Artwork adorns the walls, and greenery adds a touch of life to the space, enhancing the welcoming atmosphere.
Apartment in West Dundee
4.92 out of 5 average rating, 181 reviews

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

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Guest favourite
A treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.
Treehouse in Schaumburg
4.94 out of 5 average rating, 887 reviews

Enchanted Garden Treehouse (Amenity*)

Summer's here, the treehouse air conditioned and cozy, and the hot/cool tub ready! Relax in our luxurious, 420 friendly, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The stream makes this a wildlife refuge, with many birds, squirrels, rabbit & fox. Come experience the magic and make a special memory! See why Chgo Magazine rates us top 3 staycations in Chgo!

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Top Guest favourite
A single-story ranch home is presented with a dark blue exterior and white shutters. A neatly trimmed lawn and concrete pathway lead to the front door. Flanking the entrance, small shrubs add greenery, while a tall evergreen tree stands nearby.
Home in Montgomery
4.88 out of 5 average rating, 177 reviews

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.

LocationFamilyGetting around

Top Guest favourite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Apartment in Aurora
4.98 out of 5 average rating, 277 reviews

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.

LocationFamilyView

Top Guest favourite
A spacious living area features hardwood floors and high ceilings, providing a welcoming ambiance. Modern furniture includes a light-colored sofa and a round coffee table. An entertainment system is positioned near a large window, while a dining table is visible in the adjacent space.
Home in Aurora
5.0 out of 5 average rating, 52 reviews

Spacious 4 Beds w/ Yard – Near Naperville, Chicago

Enjoy comfort and convenience at this stylish 3-bedroom home with plenty of space to relax both inside and out! 🛋️ 2 Cozy Living Rooms 🌳 Beautifully landscaped and fenced backyard – Great for Kids! 🛏 3 Bedrooms All on the 2nd Floor ✔️ 2.5 Bathrooms ✔️ Less than 5 Mins to Fox Valley, shopping, and entertainment ✔️ 8 Mins to Phillips Park Zoo & Aquatic Center ✔️ 18 Mins to Downtown Naperville, ✔️ 50 Mins to Downtown Chicago ✔️ Free Driveway and Street Parking Available

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Top Guest favourite
The living area features a comfortable seating arrangement with a sofa and two armchairs. A round coffee table sits in the center on a patterned area rug. Soft lighting enhances the neutral wall tones, while a decorative plant adds a touch of greenery.
Apartment in Warrenville
4.94 out of 5 average rating, 133 reviews

“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!

ValueFamilyBackyard

Top Guest favourite
A functional kitchen area features wooden cabinetry and modern appliances. Ample countertop space is complemented by tile flooring. A small dining table with chairs is positioned near a window, allowing natural light to illuminate the space. A doorway leads to a cozy bedroom.
Guest suite in Oswego
4.95 out of 5 average rating, 85 reviews

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!

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Top Guest favourite
A tranquil lake scene is depicted, featuring autumnal trees reflecting vibrant hues of yellow, orange, and red in still water. The grassy shoreline enhances the serene environment, while neighboring greenery contributes to the picturesque landscape.
Guest suite in Naperville
4.96 out of 5 average rating, 559 reviews

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.

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Superhost
A cozy bedroom features a spacious bed with dark blue pillows and a textured green blanket. Two geometric lamps provide soft lighting on either side of the bed. A decorative moon wall hanging adds visual interest above the headboard, while a plush throw and rolled towel sit at the foot of the bed.
Apartment in Aurora
4.84 out of 5 average rating, 62 reviews

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,

LocationWalkabilityLong stay

Superhost
Home in Montgomery
4.85 out of 5 average rating, 20 reviews

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.

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Guest favourite
Apartment in Aurora
4.78 out of 5 average rating, 120 reviews

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.

ValueFamilyLaundry

Guest favourite
A modern living space features a spiral staircase leading to an upper level. Exposed brick and ductwork are complemented by pendant lighting. A comfortable sofa, shelving unit, and television create a functional area for relaxation and entertainment.
Apartment in Aurora
4.92 out of 5 average rating, 53 reviews

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!

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Popular amenities for Montgomery holiday rentals