Oswego Holiday Rentals
10.0
Exceptional
(33 Reviews)
- Chicago
- Plainfield
- 2.31 mi to center
3500 ft²
14 Guests
8 Bedrooms
5 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
د.إ.3,210/Night
For 7 Nights د.إ.22,472
6.5
Good
(2 Reviews)
1603.82 ft²
8 Guests
4 Bedrooms
1 Bathroom
House
- Parking
- Air Conditioner
- Internet
د.إ.672/Night
For 7 Nights د.إ.4,704
9.0
Exceptional
(924 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
د.إ.456/Night
For 7 Nights د.إ.3,191
10.0
Exceptional
(6 Reviews)
- Chicago
- Boulder Hill
- 0.83 mi to center
1400 ft²
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.951/Night
For 7 Nights د.إ.6,658
9.4
Exceptional
(19 Reviews)
118.4 ft²
5 Guests
2 Bedrooms
1 Bathroom
Apartment
- Fireplace/Heating
- Balcony/Terrace
- View
د.إ.413/Night
For 7 Nights د.إ.2,894
10.0
Exceptional
(3 Reviews)
3218 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
د.إ.3,470/Night
For 7 Nights د.إ.24,294
10.0
Exceptional
(3 Reviews)
1500 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
د.إ.1,984/Night
For 7 Nights د.إ.13,889
10.0
Exceptional
(2 Reviews)
1000 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
د.إ.1,169/Night
For 7 Nights د.إ.8,186
9.8
Exceptional
(11 Reviews)
- Illinois
- Fox Valley
- 0.56 mi to center
1356 ft²
9 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.1,152/Night
For 7 Nights د.إ.8,065
Luxury Holiday Rentals in Oswego
Over 70+ Luxury Holiday Rentals in or Near Oswego
New
3000 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.2,713/Night
For 7 Nights د.إ.18,990
New
- Chicago
- Plainfield
- 3.09 mi to center
2937 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.2,238/Night
For 7 Nights د.إ.15,667
New
- Chicago
- Plainfield
- 3.09 mi to center
2938.55 ft²
6 Guests
1 Bedroom
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Parking
- Internet
د.إ.2,046/Night
For 7 Nights د.إ.14,319
New
1452 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.1,849/Night
For 7 Nights د.إ.12,946
9.0
Exceptional
(38 Reviews)
15 Guests
5 Bedrooms
3 Bathrooms
Pet Friendly
House
- Pet Friendly
- Air Conditioner
- Internet
د.إ.1,797/Night
For 7 Nights د.إ.12,578
New
- Illinois
- Fox Valley
- 3.21 mi to center
3500 ft²
8 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
د.إ.1,695/Night
For 7 Nights د.إ.11,866
10.0
Exceptional
(3 Reviews)
- Chicago
- Boulder Hill
- 0.76 mi to center
2000 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
د.إ.1,537/Night
For 7 Nights د.إ.10,760
9.4
Exceptional
(6 Reviews)
14 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
د.إ.1,514/Night
For 7 Nights د.إ.10,599
6.0
Good
(1 Review)
- Illinois
- Fox Valley
- 2.57 mi to center
12 Guests
5 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
د.إ.1,505/Night
For 7 Nights د.إ.10,540
Top-Rated Holiday Rentals with a Pool in Oswego
Over 7+ The Best Private Villas and Holiday Rentals in Oswego with a Pool
8.8
Fabulous
(858 Reviews)
- Illinois
- Fox Valley
- 2.95 mi to center
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
د.إ.307/Night
For 7 Nights د.إ.2,152
8.5
Fabulous
(117 Reviews)
333.68 ft²
1 Bathroom
Ocean View
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
د.إ.909/Night
For 7 Nights د.إ.6,364
8.2
Excellent
(554 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.433/Night
For 7 Nights د.إ.3,030
7.6
Very Good
(107 Reviews)
351.62 ft²
12 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
د.إ.496/Night
For 7 Nights د.إ.3,474
7.1
Very Good
(371 Reviews)
258.33 ft²
1 Bathroom
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
د.إ.401/Night
For 7 Nights د.إ.2,806
10.0
Exceptional
(4 Reviews)
- Illinois
- Fox Valley
- 3.77 mi to center
12 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
د.إ.5,558/Night
For 7 Nights د.إ.38,903
New
- Illinois
- Fox Valley
- 4.52 mi to center
11 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
د.إ.7,663/Night
For 7 Nights د.إ.53,644
Pet-Friendly Holiday Rentals in Oswego
Over 33+ Pet-Friendly Holiday Rentals in or Near Oswego
9.6
Exceptional
(5 Reviews)
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.701/Night
For 7 Nights د.إ.4,903
New
1496.18 ft²
8 Guests
2 Bedrooms
3 Bathrooms
House
- Balcony/Terrace
- Pet Friendly
- Parking
د.إ.918/Night
For 7 Nights د.إ.6,427
9.6
Exceptional
(4 Reviews)
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.606/Night
For 7 Nights د.إ.4,242
9.4
Exceptional
(17 Reviews)
- Chicago
- Boulder Hill
- 0.60 mi to center
1500 ft²
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.849/Night
For 7 Nights د.إ.5,938
9.4
Exceptional
(16 Reviews)
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
د.إ.798/Night
For 7 Nights د.إ.5,590
9.2
Exceptional
(105 Reviews)
- Illinois
- Fox Valley
- 0.78 mi to center
2648 ft²
9 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.1,022/Night
For 7 Nights د.إ.7,150
8.0
Excellent
(5 Reviews)
- Chicago
- Montgomery
- 1.31 mi to center
1000 ft²
8 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.829/Night
For 7 Nights د.إ.5,803
10.0
Exceptional
(5 Reviews)
- Illinois
- Fox Valley
- 2.21 mi to center
2900 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
د.إ.1,111/Night
For 7 Nights د.إ.7,775
8.8
Fabulous
(5 Reviews)
- Chicago
- Montgomery
- 0.75 mi to center
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
د.إ.1,358/Night
For 7 Nights د.إ.9,508
Large Holiday Rentals and Private Villas in Oswego
Over 9+ Large Holiday Rentals and Private Villas in or Near Oswego
9.2
Exceptional
(26 Reviews)
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
د.إ.1,311/Night
For 7 Nights د.إ.9,178
7.8
Very Good
(13 Reviews)
- Chicago
- Plainfield
- 3.76 mi to center
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.1,481/Night
For 7 Nights د.إ.10,367
New
3000 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.1,075/Night
For 7 Nights د.إ.7,525
New
2880 ft²
8 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.1,480/Night
For 7 Nights د.إ.10,356
8.8
Fabulous
(6 Reviews)
1900 ft²
12 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.1,361/Night
For 7 Nights د.إ.9,526
5.0
Average
(2 Reviews)
- Chicago
- Montgomery
- 1.21 mi to center
1600 ft²
10 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Air Conditioner
د.إ.507/Night
For 7 Nights د.إ.3,548
4.8
Average
(6 Reviews)
- Chicago
- Montgomery
- 1.12 mi to center
16 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Kitchen
- Air Conditioner
- Internet
د.إ.929/Night
For 7 Nights د.إ.6,504
New
- Illinois
- Fox Valley
- 2.07 mi to center
2200 ft²
8 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,076/Night
For 7 Nights د.إ.7,532
New
- Illinois
- Fox Valley
- 2.07 mi to center
1750 ft²
12 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.955/Night
For 7 Nights د.إ.6,684
Oswego Private Villas and Holiday Homes Under $200
Over 17+ Oswego Private Villas and Holiday Homes Under $200
10.0
Exceptional
(4 Reviews)
1100 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.544/Night
For 7 Nights د.إ.3,808
10.0
Exceptional
(1 Review)
- Illinois
- Fox Valley
- 0.50 mi to center
900 ft²
1 Guest
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
د.إ.452/Night
For 7 Nights د.إ.3,166
New
3000 ft²
6 Guests
2 Bedrooms
3 Bathrooms
House
د.إ.730/Night
For 7 Nights د.إ.5,112
10.0
Exceptional
(1 Review)
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
د.إ.392/Night
For 7 Nights د.إ.2,743
6.0
Good
(2 Reviews)
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
د.إ.320/Night
For 7 Nights د.إ.2,237
5.0
Average
(1 Review)
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Kitchen
- Air Conditioner
- Laundry
د.إ.466/Night
For 7 Nights د.إ.3,265
1.5
Average
(2 Reviews)
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Air Conditioner
د.إ.422/Night
For 7 Nights د.إ.2,956
New
- Illinois
- Fox Valley
- 0.43 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Kitchen
د.إ.551/Night
For 7 Nights د.إ.3,856
New
- Illinois
- Fox Valley
- 2.10 mi to center
1200 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Air Conditioner
د.إ.395/Night
For 7 Nights د.إ.2,769
Instantly Bookable Holiday Homes in Oswego
Over 12+ Instantly Bookable Holiday Homes in or Near Oswego
New
- Chicago
- Plainfield
- 2.95 mi to center
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
د.إ.1,056/Night
For 7 Nights د.إ.7,396
10.0
Exceptional
(1 Review)
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Kitchen
- Air Conditioner
د.إ.819/Night
For 7 Nights د.إ.5,733
9.4
Exceptional
(3 Reviews)
900 ft²
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
د.إ.905/Night
For 7 Nights د.إ.6,331
8.0
Excellent
(1 Review)
1700 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
د.إ.1,242/Night
For 7 Nights د.إ.8,693
New
- Illinois
- Fox Valley
- 0.95 mi to center
1634 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.1,822/Night
For 7 Nights د.إ.12,751
New
- Illinois
- Fox Valley
- 0.19 mi to center
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.1,170/Night
For 7 Nights د.إ.8,190
New
- Illinois
- Fox Valley
- 1.13 mi to center
2067 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Air Conditioner
د.إ.1,158/Night
For 7 Nights د.إ.8,109
New
- Chicago
- Montgomery
- 2.11 mi to center
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Air Conditioner
- Child Friendly
د.إ.970/Night
For 7 Nights د.إ.6,790
New
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Kitchen
- Parking
د.إ.845/Night
For 7 Nights د.إ.5,913
Book a Last Minute Place to Stay in Oswego
About Casai's Private Villas and Holiday Rentals in Oswego
Discover more than 79 vacation rentals available in Oswego. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Oswego.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Oswego, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Oswego. On average, places to stay near Oswego offer 1035.2 ft², with nightly prices averaging د.إ.1,192.
With Casai, finding and comparing holiday rentals in Oswego is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Oswego
| Type | Count |
|---|---|
| Vacation Homes | 51 |
| Holiday Apartments | 15 |
| Cottages | 2 |
Use these Quick Filters to Find a Holiday Rental in Oswego
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Oswego.
Weather in Oswego, IL
View the weather forecast for Oswego before booking your Oswego Vacation Rentals to confirm your best time to go.
December - February
High 47°F Low 28°F
March - May
High 70°F Low 41°F
June - August
High 87°F Low 55°F
September - November
High 78°F Low 42°F
Top Attractions Around Oswego, IL
Casai offers a large selection of top attractions around Oswego . Research things to do on your vacation before you visit Oswego.
Other Places to Stay in Oswego, IL
Frequently Asked Questions About Oswego?
What are the top holiday rentals in Oswego?
With numerous options available in Oswego, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Oswego:
- WATERFRONT LUXURY HOME WILL FEEL LIKE A RESORT FOR 12 or More
- Fun, Spacious, NO STAIRS, Garage, WIFI, Sleeps 8max – Ideal for Families & Crews
- Aurora/Naperville - Classy, Spacious Family Home!
- Affordable Condo on the Lake
- Log Cabin Pickleball Oasis, Seating for Everyone, 2 Hot Tubs, Games, Deer, Pets
- Log Cabin Oasis: Pickleball, Hot Tub, Deer, Corn Hole, Board Games, Arcade, Pets
- Spacious 5-bdrm w 7 beds/2.5 Bath Ranch Home/WiFi/Pet Friendly/Quiet Street
- Wooded Oasis: Pickleball, Hot Tub, Fire Table, Deer, Corn Hole, Arcade, Popcorn
- 30 min to Chicago|2 TVs |Fireplace |W/D|Parking
- PROMO 10% WEEKLY AND 15% MONTHLY OFFnNaperville/Aurora, King Bed, Fenced Yard!
Which holiday homes in Oswego are best for families?
If you're searching for a family-friendly holiday home in Oswego, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Oswego:
- Extended Stay- Aurora FHS Rental - Shiloh
- Aurora FHS Rental - Shiloh
- River Access Game room Backyard King W/D Parking
How many Casai.ae holiday rentals are available in Oswego?
As of 2026, Casai boasts over 79 properties listed in the Oswego area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Oswego.
People Also Ask
Finding the best prices in Oswego
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