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Oswego vacation rentals

We found 157 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.

Vacation rentals with weekly discounts - Oswego

Showing deals for:Nov 14 - Nov 21

Image gallery for Pool•Outdoor Grill + Bar•Playground•3 king beds•2 Ovens•Fire table

{Outside} Gather under the glow - cozy up for laughter and fireside chats.
9.4 out of 10 rating
Exceptional
(16 reviews)

Pool•Outdoor Grill + Bar•Playground•3 king beds•2 Ovens•Fire table

Plainfield, IL

10% off
Price is CA $469
CA $4,568 total
includes taxes & fees
Pool•Outdoor Grill + Bar•Playground•3 king beds•2 Ovens•Fire table

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Find out more about Oswego

Find out more about Oswego

Why visit Oswego

  1. Family-friendly outdoor adventures: Oswego is ideal for families, offering numerous parks and recreational activities.
  2. Charming neighbourhoods: Explore serene bungalows and enjoy scenic water views close to urban conveniences.
  3. Local art scene: Stroll through downtown to experience local art and a warm, welcoming atmosphere.
  4. Variety of accommodations: Choose from cozy apartments, stylish condos, or private vacation homes for a comfortable stay.
  5. Challenging golf courses: Golf enthusiasts can enjoy the beautiful and challenging courses available in the area.

Popular types of accommodation in Oswego

Planning a getaway to Oswego? The excitement starts with selecting the perfect place to stay. Explore our top recommendations for vacation rentals, including houses, cozy apartments, and stylish condos. Whether you're seeking a charming holiday cottage or a spacious vacation home, we have the best options to ensure your stay is comfortable and memorable. Dive into your Oswego adventure with confidence, knowing you'll find the ideal accommodation for your needs!

  • Houses: The top choice for visitors seeking a spacious and comfortable stay, perfect for families or groups in Oswego.
  • Apartments: A popular option for those desiring convenient amenities and a home-like atmosphere during their visit.
  • Condos: Ideal for travellers looking for modern living spaces with shared facilities in a community setting.
  • Cabins: A charming retreat for nature enthusiasts wanting a rustic experience amidst Oswego's scenic beauty.
  • Cottages: Quaint and cozy, these rentals offer a delightful escape for those seeking a peaceful getaway.**

Top attractions in Oswego

Oswego, Illinois, is perfect for family-friendly outdoor adventures and urban exploration. Visitors can enjoy beautiful urban parks, challenging golf courses, and the charm of historic colleges and universities. With a variety of attractions that cater to both outdoor enthusiasts and those seeking a city experience, Oswego promises an enjoyable getaway for all types of travellers.

  1. Aurora University: A historic institution located 8.0km from Oswego, offering rich cultural experiences and a charming campus atmosphere that reflects its long-standing heritage.
  2. Hudson Crossing Park: Nestled in Oswego, this urban park is perfect for families, featuring outdoor activities, beautiful walking trails, and a welcoming city vibe, ideal for a day of relaxation and fun.
  3. Waubonsee Community College: Situated 9.7km from Oswego, this modern college offers a vibrant city atmosphere, with state-of-the-art facilities and diverse educational programs.

Things to do recommended for couples

For a romantic getaway in Oswego, visit Fox Valley Winery for delightful wines and a charming atmosphere. Alternatively, take a scenic drive to Acquaviva Winery, 29.0km away, where you can enjoy exquisite wines and a picturesque setting perfect for couples.

Things to do recommended for families

Experience family fun at Raging Waves Waterpark, only 8.0km away, or enjoy exciting adventures at Aurora Skate Center, also 8.0km from Oswego. Don't miss Vaughan Aquatic Center, located 11.3km away, perfect for a day of splashing around together!

Things to do recommended for groups

Groups visiting Oswego can enjoy a captivating performance at the Paramount Theater, try their luck at the Hollywood Casino Aurora, or indulge in shopping at the Chicago Premium Outlets, all within a short drive, providing a delightful mix of culture, entertainment, and city vibes.

What do I need to keep in mind when booking a vacation in Oswego

When planning your trip, whether with a group, family, or pets, or if you're seeking extended stays, it's important to prioritize your preferences. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Oswego with a group: Think about how many bedrooms you require, as well as features like a complete kitchen or outdoor space for group gatherings. Thankfully, you can easily narrow down your options on Vrbo to include all of these amenities and more.
  • Traveling to Oswego with young kids: Traveling with young children can be demanding. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is a wise choice.
  • Taking your pets with you to Oswego: For many families, a getaway isn’t truly complete without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oswego: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Oswego

Oswego, Illinois, offers a delightful blend of family-friendly activities and outdoor adventures, making it an ideal vacation spot. Explore charming neighborhoods with serene bungalows and enjoy water views, all while being close to city conveniences. Stroll through downtown for a taste of local art and a warm atmosphere filled with friendly people. Whether you're seeking relaxation or excitement, Oswego promises a memorable experience for every traveller.

  • Boulder Hill: Nestled only 3.2km from Oswego, Boulder Hill is a quaint village that invites visitors to immerse themselves in nature. Known for its stunning outdoor scenery, this area is ideal for those seeking romance and recreational activities. Adventure awaits at local campgrounds and scenic recreational areas, while nearby attractions like serene lakes and a national state park provide ample opportunities for exploration. Whether you’re picnicking by the beach or hiking picturesque trails, Boulder Hill promises a refreshing escape into the great outdoors.
  • Montgomery: Located 4.8km away from Oswego, Montgomery is a vibrant city perfect for family outings and outdoor adventures. The area boasts excellent campgrounds and shopping mall centres, making it easy for visitors to find both relaxation and entertainment. Families can enjoy the beauty of the national state park and spend quality time at urban parks and scenic lakes. With its blend of adventure and leisure, Montgomery is an ideal destination for those looking to create lasting memories with loved ones.
  • Aurora: Situated 9.7km from Oswego, Aurora stands out as a bustling city that caters to families, business travellers, and city explorers alike. The city offers a variety of shopping centres and educational opportunities, making it a hub of activity. Visitors can also discover historic college campuses, the national state park, and a vibrant stadium that hosts numerous events throughout the year. Aurora’s dynamic atmosphere, combined with its rich history and modern amenities, ensures a fulfilling experience for everyone.

Best time to go to Oswego

If you're planning a trip to Oswego, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like January and October to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January23.4°F (-4.8°C)Light RainMostly CloudySlightly LowSlightly Low
February25.7°F (-3.5°C)Light RainMostly CloudyAverageSlightly Low
March38.7°F (3.7°C)Light RainMostly CloudyAverageAverage
April48.7°F (9.3°C)Light RainMostly SunnySlightly HighSlightly Low
May60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
June70.0°F (21.1°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighSlightly High
August72.0°F (22.2°C)Light RainMostly SunnyAverageAverage
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October53.4°F (11.9°C)Light RainMostly SunnySlightly LowAverage
November40.5°F (4.7°C)Light RainMostly SunnySlightly LowAverage
December30.9°F (-0.6°C)Light RainMostly CloudyAverageSlightly High

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as this can lead to significant price differences. Moreover, extending your stay often results in additional savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's user-friendly Trip Board offers you a convenient platform to plan new trips, pick up from where you last stopped, and manage your travel arrangements. You can easily access properties you've saved or booked, which are categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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)
  • Grundy County Speedway (19.1 mi / 30.8 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)
  • Blackwell Forest Preserve (14.2 mi / 22.8 km)
  • Morton Arboretum (18.1 mi / 29.2 km)
  • Forest Preserve District of Will County (21.1 mi / 33.9 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 best area to stay in Oswego when booking a vacation rental?
When considering a vacation rental in Oswego, Illinois, a popular area to stay is the charming downtown district. This vibrant neighbourhood boasts a delightful mix of shops, cafés, and restaurants, making it an ideal spot for those who enjoy a lively atmosphere. The proximity to the Fox River adds a picturesque element, with scenic walking paths that invite leisurely strolls along the water.

You'll also find the beautiful Hudson River Park nearby, which is great for families and outdoor enthusiasts looking to enjoy picnics or play areas for children. The downtown area typically offers a variety of properties, suiting different tastes and budgets, ensuring you can find something that suits your needs.

Another excellent option is the area around the Oswego Village Hall, which features a lovely blend of residential charm and community spirit. This neighbourhood is close to the Oswego Historic District, where you can explore charming architecture and learn about the local history. The presence of local amenities, parks, and friendly community events makes this area particularly inviting for visitors.
How much does it cost to rent a vacation home in Oswego?
Prices for vacation rentals in Oswego vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oswego to more spacious homes.
Are there any discounts for Oswego vacation house rentals?
You can find great discounts on house rentals in Oswego on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Oswego?
In Oswego, vacation houses are the most popular type of rental accommodation, with several available throughout the area. These homes typically offer spacious living environments, featuring multiple bedrooms, fully equipped kitchens, and private outdoor spaces, ideal for families or larger groups. Additionally, apartments and condos are also prevalent, providing a more compact option for travellers seeking convenience. These rooms generally include modern amenities such as kitchen facilities, comfortable living areas, and access to shared recreational facilities.
Are there any family house rentals in Oswego?
In Oswego, Illinois, there are several family-friendly house rentals available that cater to groups and families looking for a comfortable stay. The neighbourhoods within and around the area offer a variety of properties, many of which include spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces for children to enjoy.
Can I find long-stay vacation rentals in Oswego?
A long-stay vacation rental in Oswego is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Oswego?
In Oswego, there are several pet-friendly house rentals available, making it an attractive destination for travellers with furry companions. The area offers a variety of accommodations, including single-family homes and townhouses, many of which come equipped with modern amenities such as full kitchens, spacious living areas, and private outdoor spaces like patios or gardens where pets can play.
Are there any remote work vacation rentals in Oswego?
In Oswego, Illinois, there are several remote work vacation rentals available, providing a suitable environment for those looking to blend work and leisure. Many of these properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces, and comfortable desk setups, making them ideal for productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oswego vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Oswego with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Oswego?
In Oswego, popular vacation rental amenities include well-equipped kitchens featuring essential appliances like refrigerators, microwaves, and cookware. Many properties also provide coffee makers, allowing guests to enjoy freshly brewed coffee at their convenience. These amenities cater to travellers seeking a cozy feel, ideal for preparing meals and relaxing after exploring the charming local area.
When is the best time to visit Oswego for a vacation rental?
The best time to visit Oswego for a vacation rental is during the peak season from May to July. This period is particularly popular among families and outdoor enthusiasts, as the warmer temperatures create a friendly space for a variety of activities. Expect daytime highs in the mid to high 20s Celsius, great for enjoying local parks, riverside picnics, and outdoor festivals that abound in the area.

July stands out as the most vibrant month, offering a lively community spirit with numerous events and activities. Families can take advantage of the seasonal farmers' markets and enjoy summer concerts, all while soaking in the picturesque surroundings. With so much happening, it's a fantastic time to connect with fellow travellers and make unforgettable memories.

For those looking to save a bit while still enjoying the charms of Oswego, consider planning your visit in November. This quieter month allows for a more relaxed experience, providing ample opportunities for exploring the local shops and enjoying the serene beauty of the area as it transitions into autumn.
How early should I book a Oswego vacation rental?
Book your Oswego vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Oswego home rental booking on Vrbo?
To find Oswego vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Oswego vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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