A stone bridge over a calm river, surrounded by lush greenery and buildings.

Oswego Holiday Rentals

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Our top choices for Oswego holiday rentals

1. River Access•Game room•Backyard•King•W/D•Parking

River Access•Game room•Backyard•King•W/D•Parking
Yorkville
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely loved this place. The backyard was amazing and the house was clean and had everything we needed."
United States
Daniela M.
The price is NZ$666
includes taxes & fees
16 Nov - 17 Nov
River Access•Game room•Backyard•King•W/D•Parking

2. Cozy condo

Cozy condo
Aurora
6.0 out of 10, (2 reviews)
"Good for short term stays."
United States
Lindsey H.
The price is NZ$316
includes taxes & fees
11 Nov - 12 Nov
Cozy condo

3. Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath

Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath
Aurora
7.4 out of 10, Good, (3 reviews)
"Overall good I would stay there again if I was to travel to Chicago again"
United States
Avo H.
The price is NZ$699
includes taxes & fees
7 Dec - 8 Dec
Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath

4. PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV

PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV
Naperville
9.4 out of 10, Exceptional, (33 reviews)
"It was a great stay. You will not be disappointed all our needs for a meet"
United States
Kathy R.
The price is NZ$824
includes taxes & fees
19 Nov - 20 Nov
PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV

5. 2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!

2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!
Plano
9.8 out of 10, Exceptional, (17 reviews)
"Great location, great place...perfect!"
United States
David Z.
The price is NZ$1,945
includes taxes & fees
16 Nov - 17 Nov
2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!

6. Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield

Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
Plainfield
10.0 out of 10, Exceptional, (3 reviews)
"Great host and the home location is awesome for hosting family. "
United States
Yolanda P.
The price is NZ$918
includes taxes & fees
11 Nov - 12 Nov
Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield

7. Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
Aurora
10.0 out of 10, Exceptional, (36 reviews)
"Everything was absolutely perfect, from the grounds to the out-buildings, to the main house... everything!The location was a little farther out from the city than some woule've liked, but it was the only place with parking enough to host our family reunion. There was enough sleeping, crashing, and camping space for everybody to be cmfortable and the kitchen was AMAZINGLY well equipped for anything we needed.Thank you, Veronica, for a wonderful stay!"
United States
Deborah K.
The price is NZ$1,907
includes taxes & fees
16 Nov - 17 Nov
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

8. 30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious

30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
Plainfield
9.4 out of 10, Exceptional, (18 reviews)
"Great place to stay."
United States
Taylor E.
The price is NZ$1,052
includes taxes & fees
11 Nov - 12 Nov
30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious

9. 4BR Tudor • Wooded Lot • 10 Min to Downtown

4BR Tudor • Wooded Lot • 10 Min to Downtown
Naperville
9.6 out of 10, Exceptional, (5 reviews)
"This is a spacious house in a very nice, quiet neighborhood. The backyard is a perfect spot to relax and soak in the sun/play games. This is a great house for families. We had a nearby wedding and this was a wonderful house to get ready at. The hosts are extremely welcoming and communicate wonderfully. "
United States
Alicia F.
The price is NZ$1,053
includes taxes & fees
6 Dec - 7 Dec
4BR Tudor • Wooded Lot • 10 Min to Downtown

10. King Size Bed, Work Desk, Near Hwy, Laundry Room Access, Nearby Parking

King Size Bed, Work Desk, Near Hwy, Laundry Room Access, Nearby Parking
Lockport
10.0 out of 10, Exceptional, (1 review)
"A friend and I planned a spur of the moment trip to joliet for some haunted houses and happed to find this apartment. Its pet friendly and super clean! The host is very responsive and answered all our messages promptly. I would stay here again if I was ever in the area. I highly recommend this apartment."
United States
Kathryn K.
The price is NZ$475
includes taxes & fees
11 Nov - 12 Nov
King Size Bed, Work Desk, Near Hwy, Laundry Room Access, Nearby Parking

11. - Fully-Equipped Condo - King Bed - Massive yard -

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (49 reviews)
"We had everything we needed, the host was very responsive and we would stay there again."
United States
Mike A.
The price is NZ$495
includes taxes & fees
16 Nov - 17 Nov
- Fully-Equipped Condo - King Bed - Massive yard -

12. Spacious retreat, walk to downtown and Metra

Spacious retreat, walk to downtown and Metra
Naperville
The price is NZ$660
includes taxes & fees
1 Dec - 2 Dec
Spacious retreat, walk to downtown and Metra

13. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Chicago
9.2 out of 10, Wonderful, (30 reviews)
"Nice people,nice rooms!"
United States
Anonymous traveller
The price is NZ$148
includes taxes & fees
9 Dec - 10 Dec
2 Full Beds | Non-Smoking, Kitchen

14. Renovated 2BR Near Joliet | King Bed, Parking + Patio | Sleeps 6

Renovated 2BR Near Joliet | King Bed, Parking + Patio | Sleeps 6
Crest Hill
The price is NZ$701
includes taxes & fees
16 Nov - 17 Nov
Renovated 2BR Near Joliet | King Bed, Parking + Patio | Sleeps 6

15. Large Private Studio Apartment

Large Private Studio Apartment
Lockport
The price is NZ$465
includes taxes & fees
9 Dec - 10 Dec
Large Private Studio Apartment

16. Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Geneva
9.6 out of 10, Exceptional, (29 reviews)
"The location is amazing! What a cute place. Just right for two people."
United States
Shara B.
The price is NZ$540
includes taxes & fees
11 Nov - 12 Nov
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

17. River Park Paradise w/ Fire Pit & Chef's Kitchen

River Park Paradise w/ Fire Pit & Chef's Kitchen
Bolingbrook
10.0 out of 10, Exceptional, (17 reviews)
"Excellent just what we were looking for"
United States
Sue B.
The price is NZ$1,614
includes taxes & fees
11 Nov - 12 Nov
River Park Paradise w/ Fire Pit & Chef's Kitchen

18. Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong

Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
Naperville
The price is NZ$943
includes taxes & fees
16 Nov - 17 Nov
Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong

19. - Beautiful Condo - King Bed - Free Waffle Breakfast -

- Beautiful Condo - King Bed - Free Waffle Breakfast -
Geneva
9.8 out of 10, Exceptional, (32 reviews)
"This is the perfect place to stay in Chicago "
United States
Cool boss 3.
The price is NZ$512
includes taxes & fees
16 Nov - 17 Nov
- Beautiful Condo - King Bed - Free Waffle Breakfast -

20. Quiet 2 Bedroom Escape Steps from Downtown Joliet

Quiet 2 Bedroom Escape Steps from Downtown Joliet
Joliet
8.0 out of 10, Very good, (3 reviews)
"Amazing communication with the host, she answered all my questions and I got a lot of great info!"
United States
Alicia H.
The price is NZ$588
includes taxes & fees
11 Nov - 12 Nov
Quiet 2 Bedroom Escape Steps from Downtown Joliet
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.
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Top Oswego Hotel Reviews

Find out more about Oswego

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oswego holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oswego. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oswego. Seeing all the best attractions is bound to make you fall in love with Oswego. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oswego short-term rentals, that won’t be hard to do.

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?

Cozy Mother-in-Law Suite w/Laundry, Kitchenette, Walk-In Closet, and Rain Shower: This holiday home rental outside of Oswego offers a garden, 1 hot tub and air conditioning to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Oswego?

With 5 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.