Photo by Anthony Martinez

Search Holiday Rentals in Oswego

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Oswego

4BR Home – Well-Furnished, Garage Included

6.8 out of 10, (3)
"Excellent. Easy location. Will book again."
4BR Home – Well-Furnished, Garage Included

2 Family-Friendly Units Near Downtown Naperville - Free Parking and Breakfast!

The price is £219
includes taxes & fees
12 Aug - 13 Aug
2 Family-Friendly Units Near Downtown Naperville - Free Parking and Breakfast!

Clarendon Hills Top Floor

7.2 out of 10, Good, (7)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor

2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!

10.0 out of 10, Exceptional, (11)
"Great location, great place...perfect!"
The price is £1,001
includes taxes & fees
24 Aug - 25 Aug
2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!

Entire house/4bd 1bath/GlenEllyn

2.0 star property
2.0 out of 10, (1)
"1. Hidden/unclear fees for "additional guests" though we never went over max amount of 10. 2. When first arrived at the house, both doors (outer door, and door access to the house) were wide open. Told host about this, she kept saying only the outer door was open. 3. One of us got locked in the only bathroom available at the house on the first night. Notified the host immediately. person had to climb out through a window. was told maintenance person was on their way. 2 hrs later, maintenance...
Entire house/4bd 1bath/GlenEllyn

Spacious 4BR Warrenville Home- Rep 1

4.0 star property
2.0 out of 10, (1)
Spacious 4BR Warrenville Home- Rep 1

Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed

9.0 out of 10, Wonderful, (2)
"It was nice and everyone was very friendly!!"
The price is £110
includes taxes & fees
12 Aug - 13 Aug
Spacious Unit w/ Free Parking and Breakfast Near I-88 Corridor - Pets Allowed

Stay on Pure Pleasure.

2.0 star property
10.0 out of 10, Exceptional, (12)
"We stayed with kids and everyone loved it. Husband had a blast fishing the area and the kids loved the sunshine. We'll be back for sure!"
The price is £130
includes taxes & fees
18 Aug - 19 Aug
Stay on Pure Pleasure.

Cozy Naperville Stay – Free Breakfast & Parking Near Downtown!

6.0 out of 10, (2)
"Nice and clean!!!! The staff are friendly and helpful and the breakfast was delicious "
The price is £115
includes taxes & fees
12 Aug - 13 Aug
Cozy Naperville Stay – Free Breakfast & Parking Near Downtown!

Spacious 4BR Home - Perfect for Groups!

Spacious 4BR Home - Perfect for Groups!

Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

9.8 out of 10, Exceptional, (23)
"We loved the location! It was perfect for us. Denise was very pleasant. We will definitely stay there again."
The price is £86
includes taxes & fees
2 Sept - 3 Sept
Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

✽ Charming Cottage ✽ close to College/Town/Station

10.0 out of 10, Exceptional, (47)
"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"
The price is £233
includes taxes & fees
2 Sept - 3 Sept
✽ Charming Cottage ✽ close to College/Town/Station

Riverfront rental

9.8 out of 10, Exceptional, (31)
"Impressive AirBb our host really knock it out of the park..Thank you we will definitely be stay again.."
The price is £191
includes taxes & fees
17 Aug - 18 Aug
Riverfront rental

Events Welcome! 12,000 SF Mansion w/ 2 Pools & Lakeview

9.6 out of 10, Exceptional, (8)
"Our trip was fantastic. We had a few questions when we checked in and Dean/Team were very helpful and informative. We spent the majority of our time in the theater and it was all you could ask for. We plan on making this our annual house for our yearly guys weekend. "
The price is £1,883
includes taxes & fees
12 Aug - 13 Aug
Events Welcome! 12,000 SF Mansion w/ 2 Pools & Lakeview

3 Comfy Units with Easy Access to City, Shops & Restaurants - Free Breakfast!

6.0 out of 10, (1)
The price is £334
includes taxes & fees
12 Aug - 13 Aug
3 Comfy Units with Easy Access to City, Shops & Restaurants - Free Breakfast!

2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail

9.8 out of 10, Exceptional, (27)
"Good location, close to the beautiful city center of Geneva and train to Chicago."
The price is £206
includes taxes & fees
2 Sept - 3 Sept
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail

4 Charming Units Near Downtown Naperville - Free Breakfast and Parking!

The price is £446
includes taxes & fees
14 Aug - 15 Aug
4 Charming Units Near Downtown Naperville - Free Breakfast and Parking!

Family Escape w/ Large Yard + Near Oakbrook Mall | LCP Collection

4.0 out of 10, (2)
"Big things: - THIS IS NOT A TWO BATH HOUSE. There is one full bathroom and a powder room. The listing is wrong, there is no second shower and we would never have booked for our party of 6 knowing this, so now you know too. - The cleaning standards are subpar, DO NOT STAY WITH YOUNG CHILDREN. So many examples I could list but, sticking with big things, the worst was the floors were so dirty everyone's feet/socks turned black and we found a plate of moldy hamburgers in the microwave. When we...
The price is £407
includes taxes & fees
3 Sept - 4 Sept
Family Escape w/ Large Yard + Near Oakbrook Mall | LCP Collection

Furnished Private home in Aurora sleeps 9 guests

9.4 out of 10, Exceptional, (86)
"Great yard to grill in the evening. Front room and family room both have TVs so kids can watch different things than the adults, if that's what you need or want. The couch in the family room is really comfortable to unwind on. Bedrooms all have their own TVs as well. The communication was amazing with the owner. They were incredibly responsive! I would definitely rent from them again if the option arises. "
Furnished Private home in Aurora sleeps 9 guests

Cozy Home | King Bed | 10P | Metra | Chicago Suburb

9.8 out of 10, Exceptional, (9)
"The house worked perfectly for our stay. Lots of seating options and a beautiful kitchen for home prepped meals. The house also gets amazing natural light with the abundance of windows."
Cozy Home | King Bed | 10P | Metra | Chicago Suburb
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Oswego Hotel Reviews

Frequently asked questions

Are there holiday rentals in Oswego?

Yes, there are holiday rentals in Oswego close to Keller's Farmstand, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Oswego has a good selection of restaurants. Make sure you have time to check out the art and museums during your trip.

What are some of the best holiday rentals that Oswego has to offer?

Clarendon Hills Top Floor: This holiday home rental outside of Oswego is equipped with a BBQ, air conditioning and free WiFi to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Oswego?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Oswego stay.

What can I see and do in Oswego?

Family-friendly attractions include Keller's Farmstand, whereas Hudson Crossing Park is a spot to enjoy the outdoors. Fox Valley Winery and Aurora University are a couple of places you'll find in the wider area.

What are holiday rentals like in Oswego?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oswego. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for families.