
House holiday rentals in Oswego
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Top-rated house rentals in Oswego
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Holiday rentals for every style
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Popular amenities for house rentals in Oswego
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.

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
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!

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

Paradise 4BR w/ Pool & Games
We recently moved backed to the Chicagoland area from Texas. We needed a place to stay while our Chicago home was being renovated. Lily’s place was perfect. It had everything we needed for the duration of our extended stay. It was well appointed. Exceptionally clean. It had all the amenities necessary for our family to live comfortably and it was close to grocery stores, shopping, restaurants, and downtown Chicago. Highly recommend.
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 !!!!

Spacious family friendly home away from home
My stay with my family was wonderful very peaceful and quiet. Everything was great. I also forgot to pack bathroom supplies and I’m so grateful that the host had basic necessities overall wonderful. I had a wonderful Mother’s Day staying. There will definitely come back again.

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!

Little Blue House
Alex's house is very comfortable, it has a great space for pets.

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.

Modern River Cabin
Nicolas is always accommodating and makes me feel at home.

Skip the hotel! Relax here!
Such a cute and cozy place! I was only here for a quick overnight work trip, but I would absolutely love to come back with my family for a more relaxing stay. The house was very clean, well-organized, and thoughtfully set up. I didn’t get a chance to use the hot tub, but it looked so inviting! Just a great little spot overall.
Private house rentals

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.

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!

Naperville Gem
My family personally found this BnB to give us what we needed. A place to stay for a large family. The floors were creaky, but that’s to come with an older property. Betty Val was an accommodating host, letting my family check in a little earlier and answer any questions I had in a timely manner. The location is also near a lot of restaurants and a very quiet area!

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.

Riverview Retreat- Engler’s Escape
Literally one of the best airbnbs I’ve ever stayed at. Very peaceful and quiet and has a homey atmosphere. Will definitely be staying here again. Ms.Dawn was also very helpful and responsive to all of my questions! Literally the perfect stay I did not want to leave.

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.

Family Friendly Farmhouse + Creek View!
We had a fantastic time staying at this place! The surroundings were beautiful. The check-in was easy and Noel was really communicative. I would highly recommend staying at this location for anyone interested in a place right outside of Chicago.
Quick stats about house rentals in Oswego
Total rentals
20 properties
Nightly prices starting at
$51 SGD before taxes and fees
Total number of reviews
780 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Destinations to explore
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- 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
- Chicago Cultural Center