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House holiday rentals in Montgomery

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Popular amenities for Montgomery house rentals

House rentals with a pool

Guest favourite
Home in Ottawa
4.93 out of 5 average rating, 72 reviews

Ottawa Oasis. Billiards. Pool. King Bed!

MagdalenaRating, 5 stars2 weeks ago
Great place for multiples families with kids. The layout was perfect. Kids were happy, and parents were able to relax.
Superhost
Home in Ottawa
5 out of 5 average rating, 3 reviews

Harbor Inn - Zuzu's Petals

Jeff - PFS AmericasRating, 5 stars1 month ago
Richard's place was great and as described. We will stay there again when in the area.
Guest favourite
Home in Bloomingdale
4.92 out of 5 average rating, 51 reviews

Now Open: Heated Pool with Entire House

TaraRating, 5 stars1 month ago
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.
Guest favourite
Home in Schaumburg
4.93 out of 5 average rating, 27 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

TeddyRating, 5 stars5 days ago
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!
Guest favourite
Home in Ottawa
4.9 out of 5 average rating, 51 reviews

Pearl Street Pool House

KetiRating, 5 stars1 day ago
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!!
Superhost
Home in Ottawa
4.83 out of 5 average rating, 12 reviews

The Nautical Nest

KaitlynRating, 5 stars4 weeks ago
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!
Guest favourite
Home in Plainfield
4.94 out of 5 average rating, 77 reviews

Beautiful Spanish style Home (w/inground pool)

BethanyRating, 5 stars1 month ago
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!!
Guest favourite
Home in Carol Stream
4.86 out of 5 average rating, 7 reviews

Spacious 4 Bed/3.5 Bath Sleeps 8+

CarmenRating, 5 stars8 months ago
Beautiful house very clean and comfortable. We'll be back very soon

Weekly house rentals

Superhost
Home in Oswego
4.71 out of 5 average rating, 7 reviews

Your Unique Stay by the Tracks | LCP Collection

NicoleRating, 5 stars1 month ago
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 !!!!
Guest favourite
Home in Elgin
4.9 out of 5 average rating, 78 reviews

Little house on the river

AnneRating, 5 stars1 week ago
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.
Superhost
Home in Aurora
4.8 out of 5 average rating, 50 reviews

Cozy Home 3BD 2 BA: Central; I-88/Outlet Mall/Park

TeniyahRating, 5 stars3 weeks ago
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.
Superhost
Home in Oswego
4.81 out of 5 average rating, 79 reviews

Moxie - w/ Game Room- 4 Kings, Sleeps 15

AndrewRating, 5 stars2 weeks ago
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!
Top Guest favourite
Home in Geneva
5 out of 5 average rating, 83 reviews

Center St. Retreat

TracyRating, 5 stars2 weeks ago
We loved staying at Kellie’s place. It was clean, safe, close to restaurants and fun things to do. Decor was fabulous!!
Top Guest favourite
Home in Aurora
5 out of 5 average rating, 27 reviews

Evergreen Retreat

KarenRating, 5 stars1 month ago
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!
Top Guest favourite
Home in Geneva
4.98 out of 5 average rating, 58 reviews

Spacious 2082 sq ft Home & 1 Mile Walk 2Town/River

KristenRating, 5 stars4 days ago
Wonderful stay in Geneva! The host was extremely helpful and communicative. The house was impeccably clean and had everything we needed.
Top Guest favourite
Home in Sycamore
5 out of 5 average rating, 16 reviews

Warm & Peaceful 2BR Home, Heart of Sycamore

JasonRating, 5 stars2 weeks ago
A+++++ and completely satisfied!

Private house rentals

Guest favourite
Home in Batavia
5 out of 5 average rating, 5 reviews

Charming Guest House on Farm

AnnaRating, 5 stars5 months ago
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.
Top Guest favourite
Home in Geneva
5 out of 5 average rating, 33 reviews

Perfect little paradise

DavidRating, 5 stars1 month ago
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.
Top Guest favourite
Home in Elgin
5 out of 5 average rating, 25 reviews

Little Blue House

JanainaRating, 5 stars4 days ago
Alex's house is very comfortable, it has a great space for pets.
Guest favourite
Home in Plainfield
4.84 out of 5 average rating, 38 reviews

Plainfield Home near Harrah’s Casino & Restaurants

RachelRating, 5 stars5 days ago
Truly enjoyed our stay. Pictures were on point, the place was definitely as identified. The extra games allowed my teens to have something to do before we went out. Definitely would stay here again.
Top Guest favourite
Home in Streamwood
4.98 out of 5 average rating, 66 reviews

Suburban Serenity~Grill, Fire pit, Big yard~

ChristineRating, 5 stars2 weeks ago
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 :)
Guest favourite
Home in Morris
4.87 out of 5 average rating, 52 reviews

Jewel by the river!

WeselleyRating, 5 stars2 weeks ago
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
Superhost
Home in Woodridge
4.9 out of 5 average rating, 31 reviews

Cozy 1-Bedroom Apartment on the Ground Floor

BryceRating, 5 stars1 week ago
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
Top Guest favourite
Home in Lombard
5 out of 5 average rating, 12 reviews

Grand Retreat/5Brs/Game Room

LynnRating, 5 stars2 weeks ago
Very nice, comfortable house with room for family to spread out. Very clean w good amenities (plus a few welcoming chocolates)! Grandkids enjoyed the PAC Man game in the game room as well as shooting baskets!

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