Vacation Rentals in Oswego, IL: Compare 10+ Sites & Save

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36 Best Vacation Rentals in Oswego (Starting from $112)

Your Unique Stay by the Tracks by LCP Collection
Your Unique Stay by the Tracks by LCP Collection
House
Oswego, IL, USA
3.9k from Oswego center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$476
Average price / night
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No Stairs Rustic Farmhouse APT King Beds/Fast WIFI
No Stairs Rustic Farmhouse APT King Beds/Fast WIFI
Apartment
Oswego, IL, 60543, United States
3.1k from Oswego center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
9.4

Superb

16 reviews

$217
Average price / night
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Paddock Mardi Gras
Paddock Mardi Gras
House
Oswego, Illinois, USA
5.3k from Oswego center

Parking, Air Conditioner, Internet, Child Friendly

4 Bedrooms8 Guests
6.5

Good

2 reviews

$183
Average price / night
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Rustic Studio Apt. 2 min drive to Downtown Oswego
Rustic Studio Apt. 2 min drive to Downtown Oswego
Apartment
Oswego, IL, 60543, United States
3.1k from Oswego center

AC, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom3 Guests
9.6

Exceptional

4 reviews

$165
Average price / night
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The Little Amazon
The Little Amazon
Apartment
Montgomery, IL, USA
7.8k from Oswego center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms5 Guests
9.4

Superb

19 reviews

$112
Average price / night
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Studio - Sleeps 3 - 2 mins from Downtown Oswego
Studio - Sleeps 3 - 2 mins from Downtown Oswego
Apartment
Oswego, IL, 60543, United States
3.1k from Oswego center

AC, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

1 Bedroom3 Guests
9.6

Exceptional

5 reviews

$141
Average price / night
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3 bedroom 3 bath lovely home in Aurora IL
3 bedroom 3 bath lovely home in Aurora IL
House
Aurora, IL, USA
9.4k from Oswego center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

2 Bedrooms8 Guests
New to Booking
$250
Average price / night
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Moxie- w/ Game Room- 4 Kings, Sleeps 15
Moxie- w/ Game Room- 4 Kings, Sleeps 15
House
Oswego, IL, 60543, United States
3.6k from Oswego center

AC, Dryer, Extra Bed, Internet, Laundry, Living Area, Washer

5 Bedrooms15 Guests
9.0

Fabulous

38 reviews

$489
Average price / night
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\nCozy ranch with 4 bedrooms
\nCozy ranch with 4 bedrooms
House
Oswego, IL, 60543, United States
4.4k from Oswego center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms12 Guests
9.2

Superb

25 reviews

$356
Average price / night
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Spacious 5-bdrm w 7 beds/ 2.5 Bath Ranch Home/ WiFi / Pet Friendly/ Quiet Street
Spacious 5-bdrm w 7 beds/ 2.5 Bath Ranch Home/ WiFi / Pet Friendly/ Quiet Street
House
Montgomery, IL, 60538, United States
4.5k from Oswego center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry, Microwave

5 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$418
Average price / night
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Serene 5-Bedroom Retreat, Oswego
Serene 5-Bedroom Retreat, Oswego
House
Oswego, IL, 60543, United States
5.4k from Oswego center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

5 Bedrooms12 Guests
6.0

Review score

1 reviews

$409
Average price / night
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WATERFRONT LUXURY HOME WILL FEEL LIKE A RESORT FOR 12 or More
WATERFRONT LUXURY HOME WILL FEEL LIKE A RESORT FOR 12 or More
House
Plainfield, IL, 60585, United States
5.4k from Oswego center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

8 Bedrooms14 Guests
10.0

Exceptional

34 reviews

$890
Average price / night
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3bd/1.5bath entire home/Game room/Office/extended stays/FREE Wifi & Parking
3bd/1.5bath entire home/Game room/Office/extended stays/FREE Wifi & Parking
House
Montgomery, IL, 60538, United States
5.4k from Oswego center

AC, Arcade, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
9.4

Superb

17 reviews

$230
Average price / night
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Bring the Family! Suburban Gem in Plainfield
Bring the Family! Suburban Gem in Plainfield
House
Plainfield, IL, 60585, United States
5.5k from Oswego center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$643
Average price / night
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Fun, Spacious, NO STAIRS, Garage, WIFI, Sleeps 8max – Ideal for Families & Crews
Fun, Spacious, NO STAIRS, Garage, WIFI, Sleeps 8max – Ideal for Families & Crews
House
Montgomery, IL, 60538, United States
5.6k from Oswego center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$258
Average price / night
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Aurora/Naperville - Classy, Spacious Family Home!
Aurora/Naperville - Classy, Spacious Family Home!
House
Aurora, IL, 60503, United States
6.5k from Oswego center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms12 Guests
10.0

Exceptional

5 reviews

$302
Average price / night
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Extended Stay- Aurora FHS Rental - Shiloh
Extended Stay- Aurora FHS Rental - Shiloh
House
Aurora, IL, 60503, United States
6.9k from Oswego center

AC, Arcade, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

3 Bedrooms8 Guests
New to Booking
$339
Average price / night
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Aurora FHS Rental - Shiloh
Aurora FHS Rental - Shiloh
House
Aurora, IL, 60503, United States
7.0k from Oswego center

AC, Arcade, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Internet

3 Bedrooms8 Guests
New to Booking
$332
Average price / night
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Private Pickleball Retreat, Seating for Everyone, 2 Hot Tubs, Games, Deer
Private Pickleball Retreat, Seating for Everyone, 2 Hot Tubs, Games, Deer
Cabin
Yorkville, IL, 60560, United States
8.0k from Oswego center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms12 Guests
10.0

Exceptional

3 reviews

$1096
Average price / night
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2bdrms/1.5bath-5beds/Quiet/Laundry/Jungle Theme/FREE Wifi/Sleep6
2bdrms/1.5bath-5beds/Quiet/Laundry/Jungle Theme/FREE Wifi/Sleep6
House
Montgomery, IL, 60538, United States
8.0k from Oswego center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms8 Guests
8.0

Good

5 reviews

$226
Average price / night
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Wooded Retreat, Relaxing Hot Tub, Movie Night - Popcorn & Surround Sound, Pets!
Wooded Retreat, Relaxing Hot Tub, Movie Night - Popcorn & Surround Sound, Pets!
House
Yorkville, IL, 60560, United States
8.2k from Oswego center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$314
Average price / night
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Kaleidoscope: Located in Montgomery - 4 BR, 2BA
Kaleidoscope: Located in Montgomery - 4 BR, 2BA
House
Montgomery, IL, 60538, United States
8.3k from Oswego center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms12 Guests
8.8

Fabulous

5 reviews

$511
Average price / night
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Relaxing Retreat: Hot Tub, Hot Cocoa, Fire Pit, Movie Night with Popcorn, Games
Relaxing Retreat: Hot Tub, Hot Cocoa, Fire Pit, Movie Night with Popcorn, Games
Cabin
Yorkville, IL, 60560, United States
8.4k from Oswego center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$518
Average price / night
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PROMO 10% WEEKLY AND 15% MONTHLY OFF\nNaperville/Aurora, King Bed, Fenced Yard!
PROMO 10% WEEKLY AND 15% MONTHLY OFF\nNaperville/Aurora, King Bed, Fenced Yard!
House
Aurora, IL, 60504, United States
8.7k from Oswego center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms9 Guests
9.8

Exceptional

11 reviews

$313
Average price / night
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Aurora FHS Rental - Johnston Dr - Extended - 2 bedrooms
Aurora FHS Rental - Johnston Dr - Extended - 2 bedrooms
House
Aurora, IL, 60506, United States
8.9k from Oswego center

2 Bedrooms6 Guests
New to Booking
$198
Average price / night
Check Availability
Aurora FHS Rental - Johnston Dr 2 bedrooms
Aurora FHS Rental - Johnston Dr 2 bedrooms
House
Aurora, IL, 60506, United States
9.0k from Oswego center

2 Bedrooms6 Guests
New to Booking
$274
Average price / night
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Cozy Comfort/ 2-Bedroom Plainfield Getaway
Cozy Comfort/ 2-Bedroom Plainfield Getaway
House
Plainfield, IL, 60585, United States
9.1k from Oswego center

AC, Free Parking, Heater, Laundry, Microwave, No Smoking, TV, Washer

2 Bedrooms5 Guests
New to Booking
$287
Average price / night
Check Availability

Other accommodation types in Oswego:

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Oswego.

Oswego Vacation Rentals on the Map

Frequently Asked Questions

You can explore 36 verified vacation rentals in Oswego. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Oswego vary depending on the season, property size, and location. Rates typically start from around $112 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Oswego include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Oswego welcome pets. Currently, 22 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Oswego often include amenities such as Fireplace/Heating, Laundry, and Bedding/Linens. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.