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Oswego vacation rentals

We found 133 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Oswego to find one that's perfect for your trip. Vacation rentals provide the amenities you need and want for your family, friends, or furry companion, such as parking and a washer and dryer. What you'll find is a rental for everyone's needs, including places that are non-smoking or accessible.
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    Enjoy full kitchens, laundry, pools, yards and more
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  • A place for everyone
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Travel to artsy Oswego

The area's art galleries and museums are just a few of the reasons to vacation in Oswego. Travelers 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

Do you want to discover things to do while you're in the area? Venture out of your cozy vacation rental and check out everything that Oswego has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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 looking for exciting outdoor activities or just want to appreciate the scenery, Oswego is a great spot to appreciate mother nature. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city center:

  • 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)

Transportation options to and around Oswego

Fly into Chicago, IL (DPA-Dupage), the closest airport, located 16.2 mi (26.1 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Chicago O'Hare Intl. Airport (ORD), which is 30.7 mi (49.4 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Oswego?
Apartments are the most popular type of vacation rental in Oswego, according to our data. Even if you have a different idea about what you’d like, Vrbo has properties in loads of shapes and sizes. Filter our options to find your perfect Oswego pad.
How much does it cost to rent a vacation rental in Oswego?
The average price for a vacation rental in Oswego is based on several factors, such as property type, length of stay and season. Whether you’re thinking about a sprawling villa with space for the whole family or a cozy cottage for just you and your sweetheart, just add your dates of travel to discover stays with exceptional value.
How much does it cost to rent a beach house in Oswego?
Prices for beach houses in Oswego vary depending on the type and size of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and the number of guests to see available options and prices. From there you can use our filters to narrow your search by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Oswego?
Pack a travel bag and a bone for the pooch in your life because Oswego has 10 stays that put out the welcome mat to pets. Let your four-legged friend enjoy the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates and destination, then check the “Pets allowed” filter box.
Can I rent a house with a pool in Oswego?
Tick the “pool” box in our handy filter tool and choose from two houses with private pools in Oswego on Vrbo. Morning dip, sunset soak or midnight swim? Downtime is up to you when your vacation home comes with a swimming pool.
What are popular rental amenities in Oswego?
When it comes to rental amenities that people are on the lookout for in Oswego, a fireplace, a swimming pool and a barbecue grill rank highest. With Vrbo vacation rentals, there are options to fit your style and taste, whether you’re going away with your partner, your family or even pets.
Are there large group vacation rentals in Oswego?
Oswego has three vacation homes that can fit 10 or more people. These stays come with plenty of space to share good times with loved ones.
Are there vacation rentals in Oswego that welcome kids?
Oswego has 10 family-friendly vacation homes. And finding a stay that welcomes children is a breeze with Vrbo’s “Properties good for families” filter. Besides having the whole place to yourselves, you’ll have access to conveniences and perks like extra bedrooms, full kitchens and yards.
What are the top attractions for families in Oswego?
If you’re traveling with the kids, stick these family-friendly attractions in Oswego on your to-do list:

  • Hudson Crossing Park
  • Keller’s Farmstand

Are there one-bedroom vacation rentals in Oswego?
Yes, Oswego has three one-bedroom rentals available. Usually situated in sought-after areas due to their smaller size, a one-bedroom rental is ideal if you’re getting away with a buddy or your partner. And with plenty of home comforts like laundry facilities and more privacy than a standard hotel, you’ll be able to relax while sightseeing around this exciting destination.
Can I find two-bedroom vacation rentals in Oswego?
Oswego has two two-bedroom properties that you can choose from. Enjoy a vacation home with all the comfort and privacy you want at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Oswego?
Pick from four vacation rentals with WiFi in Oswego. If you want to disconnect from the world while on vacation, but still need to be connected to the internet, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Oswego?
Oswego has eight vacation rentals where you can relax and recharge in air-conditioned comfort. To book a stay on Vrbo that offers this perk, enter your dates of travel and use the filter tool to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Oswego?
We recommend you check with the Oswego vacation home you want on Vrbo as the minimum age differs. However, it’s normally 16, 18 or 21.
How long can I rent a vacation rental in Oswego for?
How long you can rent a vacation rental in Oswego varies according to the property. Just enter your preferred dates to display a list of options offering extended stays. With loads of creature comforts such as full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to discover somewhere perfect to call your home away from home in Oswego.
Does Vrbo offer discounts for vacation homes in Oswego?
On Vrbo, you’ll find amazing discounts and deals for Oswego. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re off on a mini vacay or a longer stay, Vrbo has options for every budget and style.

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