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

Oswego Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Oswego vacation 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 AED 560
AED 1,380 total
includes taxes & fees
12 Nov - 13 Nov
River Access•Game room•Backyard•King•W/D•Parking
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with seating.

2. 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 AED 810
AED 1,595 total
includes taxes & fees
9 Nov - 10 Nov
PROMO 15% MONTHLY DISCOUNT! California King Bed, Fast Wi-Fi and 75" Smart TV
A living room with a gray sofa, a blue chair, a fireplace, and a ceiling fan.

3. 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 AED 456
AED 1,086 total
includes taxes & fees
8 Nov - 9 Nov
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.

4. 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 AED 592
AED 1,452 total
includes taxes & fees
2 Dec - 3 Dec
Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath
A patio area with outdoor furniture, a gazebo, and a barbecue grill.

5. 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.
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
Immediately feel at home when you step into the grand entryway.

6. 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 AED 1,128
AED 4,255 total
includes taxes & fees
16 Nov - 17 Nov
2-Acre Retreat on the Fox River with Spectacular Views & Hot Tub!
(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.

7. 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 AED 815
AED 2,288 total
includes taxes & fees
9 Nov - 10 Nov
30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious
A wooden deck with wicker furniture and a view of a green landscape.

8. 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 AED 1,837
AED 2,199 total
includes taxes & fees
8 Nov - 9 Nov
Spacious 5-bedroom house in perfect Plano with AC for relaxing stays
A modern kitchen with a central island, bar stools, and pendant lighting.

9. 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.
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.

10. 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 AED 845
AED 2,289 total
includes taxes & fees
6 Dec - 7 Dec
4BR Tudor • Wooded Lot • 10 Min to Downtown
A kitchen with white cabinets, a stainless steel sink, and a light-colored countertop.

11. Cozy condo

Cozy condo
Aurora
6.0 out of 10, (2 reviews)
"Good for short term stays."
United States
Lindsey H.
Cozy condo
A modern living room with a sofa set, a coffee table, and a rug.

12. 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 AED 837
AED 1,873 total
includes taxes & fees
9 Nov - 10 Nov
Spacious 4BR Home Family & Pet-Friendly 2 Living Rooms + Game Fun in Plainfield
A wooden interior hallway with a staircase, a wooden wardrobe, and a cabinet with glass doors.

13. 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 AED 1,678
AED 3,130 total
includes taxes & fees
8 Nov - 9 Nov
River Park Paradise w/ Fire Pit & Chef's Kitchen
A modern living room with a wooden dining table, two brown leather chairs, a green sofa, and a coffee table. A flat-screen TV is mounted on the wall, and a forest mural is visible.

14. Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Geneva
9.4 out of 10, Exceptional, (38 reviews)
"This is our second time at this property and we will be back. Cita the host is top notch and bent over backwards for every request. lovely neighborhood for walking and quiet. The space is perfect for a quiet dinner with our grown kids. Thank you Cita and the cleaning crew who made it beautiful!"
United States
Gail F.
The price is AED 115
AED 729 total
includes taxes & fees
30 Nov - 1 Dec
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
A covered outdoor seating area with wicker furniture, a sign reading 'Our Happy Place,' and a view of trees through large windows.

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

Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
Naperville
The price is AED 631
AED 1,771 total
includes taxes & fees
9 Nov - 10 Nov
Naperville Oasis: 3 Kings, Yard, Patio, Ping-Pong
Dining

16. 4 BR 3 BATH Naperville Downtown with Wi-fi Desk, Near HighwayTrainStation

4 BR 3 BATH Naperville Downtown with Wi-fi Desk, Near HighwayTrainStation
Naperville
6.8 out of 10, (3 reviews)
"My God the host was extremely helpful and responsive when reaching out, place was super clean, place and area was super peaceful and quiet. She over delivered guys"
United States
Marquis M.
The price is AED 2,130
AED 3,060 total
includes taxes & fees
8 Dec - 9 Dec
4 BR 3 BATH Naperville Downtown with Wi-fi Desk, Near HighwayTrainStation
A modern living room with a sofa, coffee table, and bar stools. There is a kitchen area with cabinets and a countertop.

17. 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 AED 481
AED 1,079 total
includes taxes & fees
9 Nov - 10 Nov
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
A living room with a sofa, two armchairs, a coffee table, and a view of a residential street.

18. Spacious retreat, walk to downtown and Metra

Spacious retreat, walk to downtown and Metra
Naperville
The price is AED 588
AED 1,293 total
includes taxes & fees
1 Dec - 2 Dec
Spacious retreat, walk to downtown and Metra
Two twin beds in a hotel room with a green accent wall, a framed picture, and a nightstand with a lamp.

19. 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 traveler
The price is AED 274
AED 303 total
includes taxes & fees
6 Dec - 7 Dec
2 Full Beds | Non-Smoking, Kitchen
A covered outdoor deck with wicker furniture, a glass-top table, and a potted plant.

20. - 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 AED 430
AED 954 total
includes taxes & fees
9 Nov - 10 Nov
- Beautiful Condo - King Bed - Free Waffle Breakfast -
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oswego Hotel Reviews

Chicago Club Inn & Suites

Chicago Club Inn & Suites

8/10 Good
"The hot tub worked well it was a relaxing night. The room was ok. In the middle of a remodel but everything was ok. The breakfast was prepared nicely."
Tommy 1-night trip
Posted 5 hours ago
Chicago Club Inn & Suites

Frequently asked questions

Are there vacation rentals in Oswego?

Yes, we give you a choice of vacation rentals in Oswego close to Keller's Farmstand, or you can select a more remote option if you're looking for extra privacy while you relax. Our travelers 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 vacation home rentals that Oswego has to offer?

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

How many vacation rentals are there in Oswego?

With 5 Expedia vacation rentals, you're sure 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 larger area.

What are vacation rentals like in Oswego?

Vacation rentals are privately owned properties you can stay in for a few days or a quick weekend in Oswego. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.