
House vacation rentals in Montgomery
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Top-rated house rentals in Montgomery
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Vacation rentals for every style
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Popular amenities for Montgomery house rentals
House rentals with a pool

Ottawa Oasis. Billiards. Pool. King Bed!
Great place for multiples families with kids. The layout was perfect. Kids were happy, and parents were able to relax.

Harbor Inn - Zuzu's Petals
Richard's place was great and as described. We will stay there again when in the area.

Rosemont 4BD2BA house with Pool
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!

Now Open: Heated Pool with Entire House
Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.

Pearl Street Pool House
This is a great weekend getaway for friends or family! Michelle was a great host by checking in with me during the first couple hours of our stay making sure that we were satisfied with everything. We had zero problems with the state of the house, pool, and hot tub. Our stay was great!

Schaumburg Oasis:Private Pool & Enchanted Garden
We stayed here while our floors were being refinished and Marzena’s Oasis did not disappoint! You can tell she takes great pride in her listing; everything was as described and more. The home was very clean with plenty of linens, dishes, and kitchen/pantry supplies. My kids left more crumbs on the floor than usual during breakfast one day…I could not find a broom so I messaged Marzena. She dropped off a stick vacuum AND some delicious treats. Above and beyond to make us feel welcome and comfortable. Thank you for a home away from home!

The Nautical Nest
We enjoyed our stay at the Nautical Nest and especially appreciate our host’s flexibility and kindness. The nest is cute and comfortable and located in a safe community. With State Parks nearby and great local eats you can’t go wrong booking here!

Relaxing Spanish style Home (w/inground pool)
Stayed here the night before my wedding with my siblings who stayed the night of the wedding. We hosted our getting ready portion here for the morning of the wedding and Olinka and Daniel were gracious enough to allow us to stay in their beautiful home. Made for gorgeous pictures and a comfortable stay both nights. Thank you!!
Weekly house rentals

Your Unique Stay by the Tracks | LCP Collection
We definitely enjoyed our stay. The house beautiful and lots of room! Even though it’s right next to train track we literally only heard the train one time it’s a very quiet and beautiful home inside and out. There is also a beautiful walking trail very close by the water. The beds are absolutely so comfortable! We would definitely choose to stay here again if we are in the area!!!! Thank you so much !!!!

Little house on the river
Beautiful view! The house was cute and clean and very comfortable. The pictures don’t do it justice! Also, the Fox River Trail is right out the back door. It’s great for walking, biking or running along the river.

Cozy Home 3BD 2 BA: Central; I-88/Outlet Mall/Park
The house was just as listed. It actually looked better than the pictures. We came into town for the Naval Boot Camp graduation. This house is FAR from there. 1+ hours away, all toll road. But the listings in the city were smaller and had fewer bathrooms. This house has 2.5 baths. We enjoyed our stay but there were a few things that could be improved. For a 1 week stay with 3 adults and 4 children, we had 4 washcloths and not enough towels. The listing said to buy whatever cleaning supplies that weren’t there but I didn’t expect to have to buy a broom. Yes a vacuum is provided but the house is hardwood and the vacuum didn’t pick up well on those floors. Also, be prepared to go shopping on your vacation for paper towels, dishwasher detergent and body wash (If you fly in and didn’t check a bag with your liquids inside). I don’t want to sound dissatisfied, because I was satisfied. But after looking at several listings, I thought those things should have been included.

Little Blue House
We enjoyed our stay. Very quiet for the location. Very clean and well kept house. The Shop next door was relatively quiet, did spook our pup a couple times while being outside. Didn’t bother me or my wife and dog at all while inside the house. We will gladly stay again at this location. Thank you again alex, you are a great host!

Evergreen Retreat
Spectacular place with so much to offer. Was pleasantly surprised with the outdoor setting. We were in town for a family wedding and the property was selected based on proximity to the venue. After this experience, we're considering scheduling a family reunion since the accommodations were so great!

Chic Cottage close to Metra large enclosed yard.
We had a wonderful experience staying at the Chic Cottage and would recommend it to any one looking for a comfortable home away from home place , available at a great price and good sub urban location with Super Markets and restaurants close by .

Little house on Prairie. Nautical theme 3 bedroom.
Gloria’s place is so cute and spacious! Having three bedrooms was so nice. The bathroom is small but manageable. The area is so pretty and convenient. We walked to a draft pub, Aurora University, ice cream, a park and downtown! It was an exceptionally wonderful stay.

Cute & Cozy Lisle, IL House Near the Best Areas
The hosts communicated well and got back to me quickly when I had questions. The house was clean and had everything we needed.
Private house rentals

Bliss in Batavia near the Fox River
What a lovely little quiet neighborhood to stay in! The home was perfect for our group of moms and kids horse showing at Lamplight. Anything we needed was responded to so quickly- and much appreciated!

Perfect little paradise
My wife and I and our two dogs visit the area every year for the Chicago Drum Show and Kathleen’s home was great for the location to the fairgrounds, restaurants in Geneva. The home was very clean and had everything we needed for a long weekend. For anyone bringing pets, this is a very pet friendly listing but the access to the yard is outside of the home. This would have been a big consideration of ours prior to booking and was only made aware of the outside situation until we got the welcome info.

Charming Guest House on Farm
We had an EXCELLENT time at Marianne's home in Batavia. The home was outfitted with everything that we required and then some. The place is even bigger than it appeared in the listings. There were sectional sofas both upstairs and in the basement that we didn't recall from the listing that provided even more sitting room with family. The property is so beautiful. We had such a wonderful time watching the horses play in the pastures directly out the window. Can't recommend these hosts or their property enough! Thanks again for a wonderful home away from home this holiday season.

Plainfield Home near Harrah’s Casino & Restaurants
Antonio’s home worked out very well! The beds were comfortable, which is always my first concern. The number of bedrooms and beds offered is always the thing I look for most. I travel with 2 young adult daughters and occasionally my parents who are in their 70’s. Antonio’s home worked out well for what we needed. We didn’t do a lot of cooking because we were in the area to help family move into the area. When I had a question Antonio was quick to respond and give guidance which i appreciate. We will keep this home in mind in the future now that we have family a neighborhood or so away! I would stay here again.

Jewel by the river!
Nice house in a quiet neighborhood near downtown. I would stay there again for sure. It's an older house, but nice and roomy and complete kitchen. Nice front porch. Wifi worked great. You do need to do a bit more clean up and sheets to the laundry when leaving but then you avoid a cleaning fee- so that can be worth the effort but do leave extra ten or 15 minutes for chores at the end

Geneva Island Park Retreat
Nice place in a convenient location. Would definitely stay again.

The Gamon Home
Great host and house. my dogs loved having the fenced back yard to run.

Cozy Batavia Residence on Prairie Path
This was a great location for our us for our tournament. The house was very clean, cozy, had lots of games, and extra linen. It’s located in a really nice location, kid friendly, and close to local amenities.
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Matthiessen State Park
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Wicker Park
- Willis Tower
- Brookfield Zoo
- The 606
- Moraine Hills State Park
- Chicago Cultural Center
- Medinah Country Club