Pet-friendly holiday rentals in Montgomery

Space & Style Near Downtown Parking+Walk To It All

A warm, curated home with two floors of living space. Perfect for families with kids, groups of friends and multi-generational living. The main floor + finished basement total 3 bdrms + 2.5 baths. Primary suite is on the main floor. Two secondary bedrooms are on the lower w/ a full bath. 20 min to downtown Chicago. Walk to dining + train+ FLW Home. Open living/dining/kitchen/sunroom. Remote work space. Coffee bar. Private entry/deck. Driveway parking. Central AC. Upstairs apartment is separate.

Vintage Charm

Welcome to The Vintage Charm! This downstairs apartment is 2 beds & 1 bath of Vintage Charm & Cozy Warmth. The walls are plaster, the ceilings are high, the floors are mostly original oak! Please note that new window AC units are in place for cooling & there is a furnace for heat. Entry is via an enclosed front porch. *Cat/Dogs on property, not in Guest Space* *Please submit pictures of any isssues* *Orkin for Pest Control, please contact host with any pest issues to arrange extra service*

Large Luxury Home: King Beds, Theater & BBQ

Relax and enjoy this sunny, fully outfitted family haven! ### FUN: Finished basement with a Movie Theater (projector), ping-pong, and PlayStation. We even have a toy-filled dresser for the kids! ### COMFORT: Fully stocked chef’s kitchen (mixer/Air Fryer), King/Queen beds, and a large master suite. ### PERKS: Huge yard with a stone patio, grill, and fire pit. Includes a 2-car garage and in-home laundry. ### SAFE: Professionally cleaned and sanitized before every stay for your peace of mind.

Home in Glen Ellyn

Beautiful 5 bedroom, 2.5 bath home in Glen Ellyn, fully furnished with everything you may need for a wonderful stay! Located in the peaceful suburbs of Glen Ellyn, the area is perfect for families or friends who would like a comfortable getaway. Located 40 minutes from downtown Chicago and Midway airport and 30 minutes from O'Hare airport. Located nearby major highways and shopping centers. Large, private and completely enclosed backyard perfect for kids to play in or a relaxed evening of BBQ!

4BR Home Near Naperville! Parking + Pickleball

Welcome to your Warrenville getaway! This 4-bedroom townhouse is perfect for families, groups, and business travelers looking for comfort, convenience, and space. With room for up to 10 guests, a lake view, and private parking, this home combines relaxation and functionality in one. Inside, enjoy a bright and airy layout with an open living and dining area, fully equipped modern kitchen, and plenty of space to unwind. The home is thoughtfully designed for longer stays and group gatherings.

Vintner's Attic- downtown Geneva!

Welcome to our Quaint, Freshly Updated, approx 600 sq ft., 2nd Floor unit in Historic downtown Geneva. This is the perfect place to come back to after a day of activities. The apartment offers a shared front screened porch and backyard, 4 blocks from Geneva Train Station to Chicago and steps from the bars, restaurants, and shops on both 3rd St and Rt 38. Bring a bicycle or walk to the River Bike Path that takes you into St. Charles or Batavia. Wifi and Cable included. Amazing Location!!!

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.

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Bliss in Batavia near the Fox River

Beautifully renovated house with and open floor plan, gourmet fully stocked kitchen, 4 bedrooms, 2.5 bathrooms and smart tv's in all the bedrooms and quick reliable wifi for all to enjoy. Home has large lot with amazing deck and 4 season room that also doubles as a separate work space as well as a smaller second workspace as . House also has a fully finished basement with 2 of the bedrooms, a full bathroom and a large theater room with a sectional sleeper sofa if more space is needed.

Spacious 4BR Modern Home—Walk to Downtown Geneva!

Spacious 4BR/3BA modern home (2,082 sq ft) in Geneva—ideal for families, groups, and pets! Main-floor king suite perfect for mobility needs. Enjoy smart TVs in every bedroom, NEW dual zone HVAC Aug 2025, fast Wi-Fi, dedicated workspace, full kitchen with granite counters, washer/dryer, kid gear, and game options. Relax in the fenced backyard with fire pit and ample seating. Free driveway & street parking. Walk to downtown shops, Fox River Trail, wine bars, and more!

Lockport Farmhouse: Private Entry+Parking By Door

Welcome to our charming Airbnb retreat in Lockport, Illinois! Enjoy the convenience of a full kitchen equipped with sleek stainless steel appliances. Kick back and relax in the cozy living room with a 55-inch smart TV featuring Roku for your entertainment needs. Convenience meets comfort with access to our on-site laundry room. Experience the perfect blend of modern amenities and rustic charm during your stay in Lockport. Book now for a delightful getaway!

Naperville/Aurora | Fenced Yard!

Our 3bd, 1.5ba house is perfect for a group of friends or family looking for a clean place in a safe neighborhood on the Naperville/Aurora border. There is plenty of space for 9 people to sleep comfortably (5 beds & a couple comfy couches), as well as 3 smart TVs, a gas grill & large, private, fully-fenced yard (including outdoor games), a desk space, & much more. Enjoy close access to main roads & many restaurants, stores, parks, & other places of need!