
House vacation rentals in Oswego
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Top-rated house rentals in Oswego
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Vacation rentals for every style
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Popular amenities for Oswego 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

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.

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!
We stayed here while in town for a wedding at heritage prairie farms. It was a convenient spot to stay for a family with little kids.

Retreat on Fox River w/ Stunning Views & Hot Tub!
We are so thankful for the entire team that responded to us when we had questions and ensured we had an amazing stay!

The Secret Garden
Loved this experience in Geneva! Great location and all the amenities you could need. Even snacks, a coffee assortment, and some beverages, which were a lovely extra touch. Mary was a great communicator and we felt right at home. Would definitely stay again!
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.

Waterfront dog friendly 3 bedroom home w/game room
Great vacation with our dogs. Couldn’t be any more dog friendly and pretty human friendly too. Great place to relax and reset. We really enjoyed being in the treetops with all of the wild life. Can’t wait to come back in the summer to float down the river. Book today, you will not be sorry.

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.

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!

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

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.
Quick stats about house rentals in Oswego
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ147 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
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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
- 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
- The Beverly Country Club