Oswego holiday lettings

We found 163 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, 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)
  • Splash Country Waterpark (6 mi / 9.6 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)

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)
  • Morton Arboretum (18.1 mi / 29.2 km)
  • Mather Woods Park (8.8 mi / 14.2 km)
  • Windsor Ridge Park (9.3 mi / 15 km)
  • Theodore Crossing Park (11 mi / 17.7 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 best area to stay in Oswego when booking a holiday rental?
When considering a holiday rental in Oswego, Illinois, a wonderful area to stay is the charming downtown district. This vibrant neighbourhood offers a delightful mix of local shops, cafes, and restaurants, providing visitors with a true taste of the community. One of the top attractions nearby is the beautiful Fox River, where you can enjoy scenic walks or even engage in activities like kayaking. Additionally, the historic Oswego Village Hall, with its picturesque architecture, is a lovely spot to explore.

Another appealing option is the area near the popular parks, such as the expansive Hudson River Park. This green space is superb for families and offers recreational facilities, walking trails, and playgrounds, making it an excellent choice for those looking for outdoor activities.

In terms of accommodation, Oswego has a range of properties available, suiting various tastes and budgets, ensuring that you can find a suitable place to stay while enjoying all the local attractions and amenities the area has to offer.
How much does it cost to rent a holiday home in Oswego?
Prices for holiday 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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oswego holiday 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 holiday rental accomodation in Oswego?
In Oswego, holiday houses are the most popular type of holiday rental, with about 12 available throughout the area. These houses typically offer spacious living environments, featuring multiple bedrooms, fully equipped kitchens, and private outdoor spaces such as gardens or patios for relaxation. Additionally, there are several condos and apartments, which provide a more compact option for travellers while still offering essential amenities like kitchen facilities and comfortable living areas.
Are there any family house rentals in Oswego?
In Oswego, Illinois, there are several family-friendly house rentals available, making it an excellent choice for those seeking a comfortable stay. The neighbourhoods offer spacious homes with ample living areas, superb for families to gather and relax. Many of these properties come equipped with full kitchens, allowing guests to prepare meals together, and outdoor spaces where children can play and families can enjoy barbecues.

Nearby, visitors can explore the scenic Fox River, which provides opportunities for walking and cycling along the riverfront paths. Additionally, the local parks, such as Hudson River Park, feature playgrounds and picnic areas, ensuring plenty of recreational options for families.
Can I find long-stay holiday rentals in Oswego?
A long-stay holiday 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 a great destination for travellers looking to bring their furry companions along. Many of these holiday homes come equipped with spacious backyards, ideal for pets to roam and play. Inside, you can expect amenities such as modern kitchens, comfortable living areas, and sometimes even pet-specific features like dog beds or bowls.

The town's location provides easy access to nearby parks, such as the beautiful Oswego East Park, where you can enjoy leisurely strolls and outdoor activities with your pets. The welcoming community atmosphere and local pet-friendly cafes enhance the experience for those travelling with animals.
Are there any remote work holiday rentals in Oswego?
In Oswego, Illinois, there are around 20 remote work-friendly holiday rentals available, making it a suitable destination for those looking to blend work and leisure. These properties typically offer amenities tailored for remote workers, such as dedicated desks, free Wi-Fi, and comfortable seating arrangements, ensuring a productive environment.

Situated near the picturesque Fox River, Oswego provides a charming backdrop with opportunities for outdoor activities, including walking trails and parks. Many rentals also come with well-equipped kitchens, allowing guests to prepare their own meals, and spacious living areas that provide a comfortable setting for both work and relaxation. Additionally, the local community boasts a variety of cafes and restaurants that can serve as alternative workspaces or spots for unwinding after a busy day. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oswego holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 rental amenities include well-equipped kitchens, allowing guests to prepare their own meals. Many rentals feature comfortable sofa beds, providing extra sleeping space for larger groups or families. Additionally, coffee and tea makers are commonly available, ensuring that guests can enjoy a warm beverage at their leisure. Work-friendly spaces are also a highlight, with desks and chairs provided in many properties, suiting those who may need to catch up on work during their stay. For added comfort, some rentals include fireplaces, creating a cosy atmosphere, especially during the cooler months.
When is the best time to visit Oswego for a holiday rental?
The best time to visit Oswego for a holiday rental is during the peak season from May to July, with July being particularly popular. This vibrant period attracts families and outdoor enthusiasts alike, as the warm weather invites a lot of activities. Visitors can enjoy local festivals, farmers' markets, and numerous outdoor adventures, all set against the charming backdrop of the Fox River.

During these summer months, temperatures can reach the low 30s Celsius, making it ideal for picnics in the park, boating on the river, or simply exploring the picturesque downtown area. The lively option is further enhanced by community events that bring people together, creating a welcoming environment for all.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, superb for those who appreciate the tranquillity of autumn in Oswego. You can enjoy leisurely strolls through the scenic landscape, with the added bonus of fewer crowds.

Ultimately, your choice will depend on whether you prefer the bustling summer vibe filled with activities or the peaceful charm of the off-season.
How early should I book a Oswego holiday rental?
Book your Oswego holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oswego?
In Oswego, visitors can enjoy a variety of attractions that showcase the charm of this suburban area. The Fox River runs through the town, offering scenic views and opportunities for outdoor activities such as kayaking and fishing. The Riverwalk is a pleasant path that allows for leisurely strolls alongside the river.

Oswego's historic downtown area features quaint shops and local eateries, making it a great spot for exploring and dining. The Oswego Public Library District also hosts various community events and activities for families.

For those interested in nature, the nearby Prairie Point Park provides open spaces and recreational facilities, including sports fields and playgrounds, which are ideal for families and outdoor enthusiasts.
Can I change or cancel my Oswego home rental booking on Vrbo?
To find Oswego holiday 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Oswego holiday 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More holiday ideas