
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 Oswego house rentals
House rentals with a pool

Harbor Inn - Out of Office
The house was beautiful and perfectly clean. We had a great time enjoying the surroundings and going out to Ottawa and Starved Rock

Ottawa Oasis. Billiards. Pool. King Bed!
It was a great stay for me and my son and his wife and my two grandsons. The boys loved all the games and us adults really liked the pool table. Didn't get to enjoy the pool while we were there cause it was too early in the season, but all in all a really nice place to relax. It's got everything you need there minus the food of course.Give it a shot you won't be disappointed.

Whole House With Hot Tub And Spacious Bedrooms
Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again

Pearl Street Pool House
Bachelorette weekend for my daughter in law to be. Loved the pool and hot tub. Beds were very comfortable. Michelle was available for all questions. Great Host!

The Nautical Nest
We had an amazing stay at Paula’s place! She was very helpful with checking in and also very responsive. The house looks exactly like the pictures. Nice neighborhood. We would definitely stay here again!

Relaxing Spanish style Home (w/inground pool)
House was lovely. I enjoyed the homes decor. Every day I woke up with something else I loved. The house had everything we needed. Only thing I wished the pool heater was working and the pillows were flat. I would definitely stay here again.

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.

$10 Cleaning Fee Promo! - Home in Elgin
I had an amazing stay at this Airbnb! The highlight was definitely the backyard — it’s beautifully maintained and perfect for relaxing. We especially enjoyed the bonfire area in the evenings, which made for such a cozy vibe. The theatre room was also a fantastic bonus — perfect for movie nights with great sound and seating. The home was clean, comfortable, and had everything we needed. I’d absolutely stay here again and recommend it to anyone looking for a peaceful and fun getaway!
Weekly house rentals

Family Friendly Duplex/9 min from MDW/Free Parking
Came for c2e2 with my friends and it was perfect for all of us! Would recommend 💗💗

Home in Glen Ellyn
Humongous place to stay for a large group. Master bedroom was so huge! Having 5 bedrooms was great. We really enjoyed our stay.

Massive 8bd/3ba Building w/ Two Car Garage!
I loved this place. Perfectly accommodated 14 adults and 3 children. Only thing it could use was at least 2 extra blankets and a sheet pan for baking. Other then that, it was perfect! Walking distance to the bus stop to get to the train stain. Aldi (grocery store) 5 minutes away walking distance.

Country charmer house near NIU
This is our second year staying at this beautiful and convenient Airbnb. Only 15 minutes from the NIU Convocation Center! Close to a great pizza place that will deliver to the Airbnb. Cynthia is very responsive and very flexible. We love this space!

Suburban Serenity~Grill, Fire pit, Big yard~
Always responsive and helpful owner. The house is just what our family needs in the area convenient for our stay in the Chicago suburbs. Will definitely return again!

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin
Great place with plenty of space. Our family really enjoyed Michael’s home.

Excellent Location for Vacation or Business Stays.
This was our second stay at Rita’s and we found it very accommodating and great of an experience as our last visit. The neighborhood is in a great location and it is cozy and quiet. The property was extremely clean. We would be happy with staying here again in the future.

RANCH, House-tel: updated full kitchen, comfy beds
This was our second time staying at Jehu's home in Itasca, IL. We have family and friends nearby so the location is perfect. The beds are comfortable, and the house is very clean. Having bottled water, coffee, a variety of beverages and snacks at our disposal was a plus. Jehu was very responsive to any questions we had. We would definitely book this property again for our next visit to the Chicagoland area.
Private house rentals

Cozy Ranch duplex close to downtown Geneva
Amazing place to stay. Jane had plenty of snacks in the house. Made cookies and snacks for us. Made us feel at home in a quiet neighborhood that was very walkable to great restaurants, coffee and donuts.

Spacious family friendly home away from home
This was a great stay, I definitely would come here again!! The host was very responsive and friendly!! I enjoyed the area very much!!😀

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath
This is the 2nd time this year we rented from Michael. He continued to impress with the responsiveness. This time we filled the whole house, all bedrooms and both floors, 12 in total, mix of kids and adults. We decorated for Christmas, made it feel like we were home for the holidays. We walked all around the neighborhood, got coffee in the morning, fresh bread from a fabulous bakery in Downtown Oak Park and always felt safe and enjoyed the friendly neighborhood. The home and bedrooms were warm when you wanted them warm during the day and cool at night to sleep in. Kitchens were well equipped and all the appliances worked perfectly. The tankless water heater was a blessing when we were all trying to get out for a family event. At one point we realized that we were out of trash bags on Christmas morning. Michael had them there in less than 30 minutes. Over the top responsiveness. Being 10 minutes from the Eisenhower makes this convenient to either Downtown or Oak Brook.

Bungalow on Vine.
Suzie’s place was great. It was clean and comfortable. We would likely stay again if visiting the area.

Big Family Home with 4 King Beds
I will be recommending this place to everyone for a nice get together. The neighborhood was nice and quiet and it is a beautiful place to relax or to have as an activity weekend. Plenty of stuff to do

Grand Victorian Mansion in Austin Area
The accommodation was spacious and very comfortable for our large group of 16. While the floors creak a bit, it wasn’t an issue. Samantha was always quick to address any questions and issues. The gated parking area provided ample space for our cars, which was a great convenience.

The Country Life! Entire House.
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.

Quiet cul-de-sac with huge fenced in backyard
Tom’s place felt right at home! Spacious backyard, quiet neighborhood, and he’s very friendly. Responded right away with any questions or comments we had! 10/10 recommend anyone to stay here if available!
Quick stats about house rentals in Oswego
Total rentals
20 properties
Nightly prices starting at
$63 AUD 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
Wi-Fi availability
20 properties include access to Wi-Fi
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- The Field Museum
- Matthiessen State Park
- Lincoln Park Zoo
- Lincoln Park
- Wicker Park
- Museum of Science and Industry
- Chicago History Museum
- Willis Tower
- Brookfield Zoo
- Flossmoor Golf Club
- Skokie Country Club
- Garfield Park Conservatory
- Chicago Cultural Center
- Promontory Point