
Holiday houses in Montgomery
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Top-rated holiday rentals in Montgomery
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Sunny Lockport Farmhouse: Studio + Full Kitchen
Experience tranquility in this charming Lockport studio, blending vintage charm with modern comforts. The studio offers a cozy queen-size bed, premium amenities, and a smart TV. The sunlit kitchen, equipped with sleek appliances and a delightful coffee nook, invites culinary adventures. Step into the vast backyard, a serene haven for relaxation or play, complete with laundry facilities for convenient living. Located on Archer Ave, enjoy easy access to I-55 and I-355. Your perfect retreat awaits!

5 bdrm/2.5 bth/Fenced Yard/Quiet St /Pet friendly
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.

AT YOUR SERVICE! Downtown Aurora River Facing Gem
Welcome to your cozy retreat in the heart of Downtown Aurora! This charming 1-bedroom apartment is perfect for up to 2 guests and offers a peaceful river view. The unit is complete with a full kitchen & is pet-friendly. Located steps from Hollywood Casino, Paramount Theatre, RiverEdge Park, and the scenic Riverwalk, you'll have easy access to local attractions. Stroll to restaurants, shops, and entertainment, making this the perfect base for exploring all that Downtown Aurora has to offer.

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.

Tranquility at the Main House at Pond View Acres
Nature lovers will enjoy observing the Pond from the Main house at Pond View Acres - a renovated, ranch-style home on 15 acres in a country setting. With a scenic view of a pond, it is surrounded by forest preserve to the west and south. Just a quick drive to shopping. Beyond the pond are walking trails that may provide wildlife sightings, such as deer, coyote, fox. This small farm is home for four mini donkeys & chickens. A garden area separates the Main house and the Guesthouse.

Cozy 4-bedroom ranch - minutes from everything
Relax and have fun with the whole family at this peaceful place to stay. It is located within walking distance from US Route 34 in the middle of shopping centers such as Meijer, Jewels, Target, Walmart, great restaurants, bars, entertainment, hair and nail salons, gas stations, etc. There are 5 beds (1 king and 4 queens plus a queen-size air mattress and a twin pull-out bed) and 3 couches waiting for their guests. The house is cleaned and sanitized before every reservation.

Riverside Cottage
Peaceful two bedroom cottage newly refurbished. Plenty of outdoor space, woods streams and walking trails nearby. Tucked out of the way of busy roads or city life but only a short drive to all the amenities of civilization. Keep an eye out for deer, ducks, beavers, hawks and other scenic wildlife out the back window/patio. There’s even a couple bald eagles that live nearby. Consider a longer stay to take advantage of discounts on 2, 4 or 7 night stays

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!

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.

Calm, Exciting, King & Queen Beds, Smart TV, WiFi
Welcome to Magic Feathers – a cozy retreat just minutes from Downtown Aurora and the Chicago Premium Outlets. Relax in the elegant Peacock Room with a king bed or the charming Owl Room with a queen bed. Enjoy a fully equipped kitchen, 75” Smart TV, fast Wi-Fi, and thoughtful touches throughout. Perfect for a peaceful stay close to everything! A few blocks from I-88.

Cozy comfortable Studio Condo
Come and relax at this cozy and comfortable studio condo in a family friendly environment. The property is located right for the main interstate so it’s very conveniently located. Just minutes away from the Chicago Prime Outlet mall and the upcoming casino and convention center.
Popular amenities for Montgomery holiday rentals
Other great holiday rentals in Montgomery

Private room in Elgin w/ Amenities & Hot Tub

Modern Naperville Room | Pool. Free Breakfast

The "Hangar" Room Echo

Private room in a nice home w/pond view

Enchanted Egyptian “Treehouse” with Soaking Tub

Cozy Room in Lower level

Skyline Room, near Medical Ctr, Upstairs

Large Private Room in Geneva, Illinois
Destinations to explore
- Chicago Holiday rentals
- Downtown Chicago Holiday rentals
- Platteville Holiday rentals
- Indianapolis Holiday rentals
- Detroit Holiday rentals
- St. Louis Holiday rentals
- Southern Indiana Holiday rentals
- Louisville Holiday rentals
- Cincinnati Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- Windsor Holiday rentals
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Matthiessen State Park
- Oak Street Beach
- The Field Museum
- Wicker Park
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606
- Olympia Fields Country Club