
House holiday rentals in Montgomery
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Top-rated house rentals in Montgomery
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Popular amenities for Montgomery house rentals
House rentals with a pool

Ottawa Oasis. Billiards. Pool. King Bed!
We had our 9 person family here with our 3 dogs and the space was perfect. Lots of games and pool time for the kids and adults alike. The charcoal grill was hard to get right but we are just not used to dealing with that type of grill! Lots of hiking in nearby areas.

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

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.

Schaumburg Oasis:Private Pool & Enchanted Garden
They were a fantastic host, very responsive to every question and anything we needed. The location is quiet and amazing, great place to relax and enjoy time. love the pool! Will definitely stay again. 100% recommend!

Pearl Street Pool House
Perfect space for a group of teens! They took full advantage of the pool area. The large bedroom on the top floor accommodated all the girls, so they could gab all night long till they fell asleep. The space is beautiful and Michelle is attentive and approach able. Already planning another stay here!!

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!

Beautiful 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!!

Spacious 4 Bed/3.5 Bath Sleeps 8+
Beautiful house very clean and comfortable. We'll be back very soon
Weekly house rentals

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.

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 !!!!

Moxie - w/ Game Room- 4 Kings, Sleeps 15
Awesome place - great for my big group of 15. Games in the basement were super fun and there was a ton of space for everyone!

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!

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!

Spacious 2082 sq ft Home & 1 Mile Walk 2Town/River
Wonderful stay in Geneva! The host was extremely helpful and communicative. The house was impeccably clean and had everything we needed.

Warm & Peaceful 2BR Home, Heart of Sycamore
A+++++ and completely satisfied!

The Secret Garden
Mary place was beautiful and very comfortable! She is a great host and check in was very easy! Whatever you need she is a text away. Great location, beautiful backyard with games. She does cooking classes too! I would give her a 10 star if I could, ill definitely be back!
Private house rentals

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.

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.

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.

Little Blue House
A Casa de Alex é muito confortável, tem um ótimo espaço para os pets.

Spacious Home in Chicago Suburbs
We enjoyed our stay very much and felt right at home. The hosts were very communicative and helpful. They were very flexible with check in and check out times. The home was fully stocked with lots of extra linens. Simple check out. Very beautiful home! I would 10/10 recommend! 🤩

Suburban Serenity~Grill, Fire pit, Big yard~
The house was very clean, easy to find, and lots of nearby parks. The beds and sofa were very comfortable. The kitchen was well-stocked with plates, pots, and silverware. Maggie was responsive and allowed us late check-out :)

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

Cozy 1-Bedroom Apartment on the Ground Floor
Iryna’s place was just what I needed for a quick stay since my family nearby didn’t have space for me. Slept wonderfully and the shower was really nice
Destinations to explore
- Downtown Chicago Holiday rentals
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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
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Brookfield Zoo
- The 606
- The Beverly Country Club
- Flossmoor Golf Club
- Moraine Hills State Park