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

2-Acre Highland Park Retreat with Heated Pool ~ 5*
We had a great stay overall. From start to finish, Kailash was extremely helpful, friendly and responsive. We needed a long-term stay with 2 big dogs, and this house worked great for us. We didn't get to use the pool much because the weather didn't cooperate, but the pool and patio area are gorgeous. The location is great, close to everything - grocery stores, restaurants, etc. There is a trail behind the house (accessible through a gate in the back yard), and it leads to a beautiful and huge forest preserve - beautiful for walks/hikes in the woods! The kitchen was a great space for us, and it had everything we might need for cooking, etc. The house was very comfortable for our family, and we would come again. Thank you, Kailash!

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.

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.

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!

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.

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 .

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.

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.

Retreat on Fox River w/ Stunning Views & Hot Tub!
We are so thankful to have stayed at this Airbnb for two weeks! It was our home away from home!

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

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!

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

Bolingbrook 4B 2ba Sleeps 8| LCP Collection
Dawn’s house was great. My family traveled to town and the space was what we expected. The beds were comfortable and the kitchen had what we needed. Dawn was very responsive with anything we needed.

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!

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.

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

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.
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
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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