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

Oswego Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Oswego holiday rentals

A modern kitchen with white cabinetry, a dining area with a wooden table and chairs, and a large island with a stove.

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 HK$1,103
HK$2,965 total
includes taxes & fees
28 Oct - 29 Oct
River Access•Game room•Backyard•King•W/D•Parking
A living room with a gray sofa, a blue chair, a fireplace, and a ceiling fan.

2. PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!

PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!
Aurora
9.2 out of 10, Wonderful, (15 reviews)
"The beds were super comfortable and the location for Naperville/Aurora/Wheaton activities was ideal--about 10 minutes or so for everything."
United States
Scott D.
The price is HK$865
HK$2,304 total
includes taxes & fees
27 Oct - 28 Oct
PROMO 10% WEEKLY AND 15% MONTHLY OFF Naperville/Aurora, King Bed, Fenced Yard!
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove.

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 HK$1,045
HK$2,853 total
includes taxes & fees
2 Nov - 3 Nov
Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath
A kitchen with white cabinets, a stainless steel sink, and a light-colored countertop.

4. Cozy condo

Cozy condo
Aurora
6.0 out of 10, (2 reviews)
"Good for short term stays."
United States
Lindsey H.
The price is HK$692
HK$1,472 total
includes taxes & fees
8 Nov - 9 Nov
Cozy condo
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with seating.

5. 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 HK$1,482
HK$3,408 total
includes taxes & fees
28 Oct - 29 Oct
PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV
A bedroom with a bed, a wall-mounted lamp, and a door.

6. 2 BR Stay MINS to Aurora Premium Outlets

2 BR Stay MINS to Aurora Premium Outlets
Aurora
8.4 out of 10, Very good, (8 reviews)
"Everything was as advertised Parking was a little complicated but that’s not controllable. Very happy with my stay"
United States
Mike W.
The price is HK$855
HK$2,169 total
includes taxes & fees
27 Oct - 28 Oct
2 BR Stay MINS to Aurora Premium Outlets
Immediately feel at home when you step into the grand entryway.

7. 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, (16 reviews)
"Great location, great place...perfect!"
United States
David Z.
The price is HK$2,243
HK$8,762 total
includes taxes & fees
27 Oct - 28 Oct
2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!
A modern living room with a sofa set, a coffee table, and a rug.

8. 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.
Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
A patio area with outdoor furniture, a gazebo, and a barbecue grill.

9. 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)
"The property was perfect for our family! There was plenty of room, indoors and out, for us, our kids, and our grandkids. The house was spotless and the kitchen was extensively stocked with dishes, cookware, etc. We also appreciated the numerous comfy places to gather."
United States
Mila M.
The price is HK$3,913
HK$9,010 total
includes taxes & fees
27 Oct - 28 Oct
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
(OUTDOOR SPACE) Where comfort and charm come together. Unwind in the outdoor lounge set under an inviting gazebo with twinkling lights. Stay fresh with a gentle breeze from the fan as you relax.

10. 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 HK$1,779
HK$5,168 total
includes taxes & fees
27 Oct - 28 Oct
30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
A modern kitchen with a central island, bar stools, and pendant lighting.

11. Spacious 7-bedroom house with AC in wonderful Naperville

Spacious 7-bedroom house with AC in wonderful Naperville
Naperville
8.0 out of 10, Very good, (1 review)
"Very smooth booking, checking in, and checking out process. The house was older, and it showed, but was big enough to hold my group. There were problems with the fire detectors randomly beeping, and some mold in the basement, but everything else was fine."
United States
Brett H.
The price is HK$3,670
HK$8,561 total
includes taxes & fees
27 Oct - 28 Oct
Spacious 7-bedroom house with AC in wonderful Naperville
A spacious living room with a fireplace, a large sofa, a coffee table, and a TV.

12. 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 HK$1,804
HK$4,970 total
includes taxes & fees
2 Nov - 3 Nov
4BR Tudor • Wooded Lot • 10 Min to Downtown
A pathway flanked by stone arches, surrounded by lush green grass and trees.

13. Spacious 5-bedroom house in perfect Plano with AC for relaxing stays

Spacious 5-bedroom house in perfect Plano with AC for relaxing stays
Plano
The price is HK$3,921
HK$4,937 total
includes taxes & fees
27 Oct - 28 Oct
Spacious 5-bedroom house in perfect Plano with AC for relaxing stays
A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a view of the outside through the windows.

14. 2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail

2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
Geneva
9.8 out of 10, Exceptional, (40 reviews)
"Property was very clean and well-kept. The neighborhood was quiet and felt safe. In a great location too, about a mile from the Metra/downtown Geneva"
United States
Ethan D.
The price is HK$988
HK$2,484 total
includes taxes & fees
2 Nov - 3 Nov
2CHICAGO Train 1MI/WIFI/KING/Free parking/Fox River Bike Trail
A modern living room with a large white table, grey sofa, and a flat-screen TV mounted on the wall.

15. King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Lockport
10.0 out of 10, Exceptional, (10 reviews)
"Adorable place to stay, decor is done so cute. Very comfortable family room to relax"
United States
Teresa S.
The price is HK$1,037
HK$2,124 total
includes taxes & fees
28 Oct - 29 Oct
King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
A covered outdoor seating area with wicker furniture, a sign reading 'Our Happy Place,' and a view of trees through large windows.

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

Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
Naperville
The price is HK$1,623
HK$4,313 total
includes taxes & fees
27 Oct - 28 Oct
Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
A wooden interior hallway with a staircase, a wooden wardrobe, and a cabinet with glass doors.

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, (16 reviews)
"Excellent just what we were looking for"
United States
Sue B.
The price is HK$3,608
HK$6,940 total
includes taxes & fees
27 Oct - 28 Oct
River Park Paradise w/ Fire Pit & Chef's Kitchen
Two twin beds in a hotel room with a green accent wall, a framed picture, and a nightstand with a lamp.

18. 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 HK$657
HK$727 total
includes taxes & fees
15 Nov - 16 Nov
2 Full Beds | Non-Smoking, Kitchen
A covered porch with wicker furniture, a coffee table, and a potted plant.

19. - 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 HK$1,108
HK$2,429 total
includes taxes & fees
27 Oct - 28 Oct
- Fully-Equipped Condo - King Bed - Massive yard -
A living room with a sofa, two armchairs, a coffee table, and a view of a residential street.

20. Spacious retreat, walk to downtown and Metra

Spacious retreat, walk to downtown and Metra
Naperville
The price is HK$1,451
HK$3,167 total
includes taxes & fees
20 Nov - 21 Nov
Spacious retreat, walk to downtown and Metra
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

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

8/10 Good
"It was ok but I expected a little more based on previous reviews. Breakfast is very basic and after two days I decided to skip it entirely."
Jerry 4-night trip
Posted less than an hour ago
SureStay Plus Hotel by Best Western Chicago Lombard

Find out more about Oswego

Search for holiday rentals in Oswego on Expedia! You can easily find your home rentals, villas, holiday apartments in Oswego using one of the methods below:

  • View our selection of featured holiday rentals in Oswego
  • Use the map to find apartments and other holiday homes in the Oswego neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oswego while they last

Look no further and take a look at our great range of rental properties in Oswego!

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.