Photo by Anthony Martinez

Oswego holiday rentals

We found holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Oswego to find one that's perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as cable TV and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Travel to arty Oswego

The area's art galleries and museums are just some of the reasons to come on holiday to Oswego. Travellers to this romantic city praise the restaurants, shopping and bird watching. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Oswego

Are you searching for top things to see and do in the area? Venture out of your holiday home and check out everything that makes Oswego a fun spot to go on holiday. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Fox Valley Winery (0.8 mi / 1.4 km)
  • Bolingbrook Golf Club (10.5 mi / 17 km)
  • Mistwood Golf Club (12.3 mi / 19.9 km)
  • Cantigny Golf Club (15.2 mi / 24.5 km)
  • Seven Bridges Golf Club (15.6 mi / 25.1 km)
  • St Andrews Golf and Country Club (18.7 mi / 30.1 km)

Exploring the natural features in Oswego

Whether you're an outdoor enthusiast or just want to take in the scenery, Oswego is a great place to get outside. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Centennial Beach (11.7 mi / 18.9 km)
  • Riverwalk Park (11.8 mi / 18.9 km)
  • Fabyan Villa Museum & Japanese Garden (13 mi / 20.9 km)
  • Morton Arboretum (18.1 mi / 29.2 km)
  • Island Park (14.3 mi / 23.1 km)
  • Belmont Prairie Nature Preserve (17.4 mi / 28 km)

Transport options to and around Oswego

Fly into Chicago, IL (DPA-Dupage), the closest airport, located 16.2 mi (26.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Chicago O'Hare International Airport (ORD), which is 30.7 mi (49.4 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Oswego?
Apartments are the most popular type of holiday home in Oswego, according to our data. Even if you have a different idea about what you want, Stayz has holiday homes in all shapes and sizes. Look through our options to find your ideal fit.
How much does it cost to rent a holiday home in Oswego?
The average price for a holiday home in Oswego is based on a number of factors, such as property type, season and length of stay. Whether you’re thinking about a sprawling villa with lots of bedrooms or a cosy cabin for just you and the kids, just add your travel dates to discover stays with unbeatable value.
How much does it cost to rent a beach house in Oswego?
Prices for beach houses in Oswego may vary depending on the type and size of the property and time of year you’re travelling. Simply enter your dates of travel into Stayz and the number of guests to view your options and prices. From there you can use the filters to tailor your search results by nearby activities, ratings, amenities and more.
Are there pet-friendly holiday homes in Oswego?
You’re in luck. There are. Choose from eight stays that welcome pets in Oswego on Stayz. Our cuddly best friends need a break too, so simply use our search function for pet-friendly holiday homes to find a pad where Fido can get in on the fun.
What are popular home amenities in Oswego?
A barbecue grill, a fireplace and nearby museums top the list of most popular home amenities in Oswego. Whether you’re travelling as a party of one, with your significant other or a group of family members, Stayz can help you find a holiday home that suits your style with all the conveniences you’re looking for.
Are there large group holiday homes in Oswego?
Oswego has two holiday homes that can cater to 10 or more guests. These properties come with all the space you need to share good times with friends and family.
Are there holiday homes in Oswego that welcome kids?
With eight family-friendly holiday homes to select from in Oswego, there’s never been a better time to introduce the little ones to the joys of travel. Check our “Properties good for families” filter box to find stays that feature amenities perfect for travelling families, like full kitchens, pools, hot tubs and entertainment areas.
What are the top attractions for families in Oswego?
Keep the kids amused at these popular family-friendly attractions in Oswego:

  • Raging Waves Waterpark
  • Splash Country Waterpark
  • Sugar Grove Family Fun Centre

Are there one-bedroom holiday homes in Oswego?
Yes, you can take your pick from three one-bedroom homes in Oswego. Whether you’re looking for a comfy cottage or a condo, our one-bedroom homes are great if you don’t need lots of space. One of the main perks of having your own pad? You won’t ever have to share your getaway with strangers.
Can I find two-bedroom holiday homes in Oswego?
Select from two two-bedroom holiday homes in Oswego. Settle the kids into the second room or maybe fill it with a couple of your nearest and dearest friends. There’s enough space for whoever’s lucky enough to be coming along.
Are there holiday homes with WiFi in Oswego?
Oswego has two holiday homes with WiFi, so you can stay connected while on holiday. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movies with your family to updating your social media, these Stayz homes will keep you online.
How can I find holiday homes with air conditioning in Oswego?
Oswego has seven holiday homes where you’ll be able to kick back in air-conditioned comfort. To locate a property on Stayz that comes with this amenity, enter your dates of travel and use the handy filter tool to select the “air conditioning” box.
How old do you have to be to rent a holiday home in Oswego?
We advise checking with the Oswego holiday property you’re looking at on Stayz as the minimum age varies. However, normally it’s 16, 18 or 21.
How long can I rent a holiday home in Oswego for?
How long you can book a holiday home in Oswego is down to the property. Just enter your chosen dates to display a list of options offering extended stays. With tons of creature comforts such as air conditioning and kitchens, as well as some offering discounted weekly or monthly prices, you’re sure to find somewhere perfect to call your home away from home in Oswego.

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