Oswego vacation rentals

We found 153 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Oswego that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation rentals have the amenities you expect for your stay, which might include cable TV and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Oswego

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Find out more about Oswego

Find out more about Oswego

Why visit Oswego

  1. Outdoor Adventures: Oswego offers scenic lakes and urban parks, perfect for hiking, fishing, and picnicking.
  2. Charming Downtown: Stroll through the friendly downtown area, ideal for family outings and leisurely exploration.
  3. Romantic Getaways: The picturesque surroundings make Oswego an excellent destination for couples seeking a romantic escape.
  4. Diverse Accommodations: Choose from charming holiday cottages, cozy cabins, and unique vacation homes tailored to every traveller's needs.
  5. Local Culture: Immerse yourself in the vibrant local culture and community events that Oswego has to offer.

Popular types of accommodation in Oswego

Planning a getaway to Oswego? You’ll love exploring the diverse vacation rentals available, from charming holiday cottages to cozy cabins and houses. Whether you're searching for seaside retreats or unique stays, Oswego has something to suit every traveller’s needs. Discover the perfect Eugene vacation rentals and cottage rentals in the United States to make your trip unforgettable!

  • Houses: The most sought-after option in Oswego, ideal for families or groups seeking a home-like atmosphere during their stay.
  • Cottages: A charming choice for those looking for a cozy retreat, perfect for a relaxing getaway amidst nature.
  • Cabins: Popular among travellers wanting a rustic experience, providing a unique connection to the outdoors.
  • Condos: A modern accommodation option offering convenience and amenities, suitable for a comfortable stay.
  • Apartments: A practical choice for visitors wanting a homey feel with easy access to local attractions.**

Top attractions in Oswego

Oswego, Indiana, is perfect for outdoor enthusiasts and those seeking a romantic getaway, offering a blend of scenic lakes, urban parks, and modern college campuses. The area provides an array of attractions that cater to families and city explorers alike, ensuring a memorable experience for all visitors. Whether you’re enjoying nature or exploring the local culture, Oswego has something special to offer everyone.

  1. Tippecanoe Lake: A serene getaway only 3.2km from Oswego, Tippecanoe Lake offers a romantic atmosphere with stunning scenery, perfect for outdoor enthusiasts and beach lovers.
  2. Grace College: Situated 11.3km away, this modern college boasts a vibrant city vibe, making it an ideal spot for those interested in education and campus life.
  3. Lakeside Park: Located 12.9km from Oswego, this urban park is perfect for families, featuring outdoor activities amidst a lively city backdrop.

Things to do recommended for couples

For a charming getaway in Oswego, consider dining at Amish Acres, located 24.1km away. This delightful restaurant offers a romantic atmosphere perfect for couples, blending city vibes with a touch of family warmth. Enjoy a memorable meal together in a cozy setting.

Things to do recommended for families

Families visiting Oswego can enjoy a day of fun at the City-County Athletic Complex, a vibrant sports facility located 12.9km away. This venue offers a variety of sports activities that will keep kids excited and engaged during your family vacation.

Things to do recommended for groups

Experience the charm of Oswego with a visit to the Wagon Wheel Theatre for a delightful performance, enjoy a round of golf at South Shore Golf Club, or explore the shops and eateries at Coppes Commons for a perfect blend of culture, sports, and family entertainment.

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

If you're planning a trip with a group, family, or pets, or if you're considering a longer stay, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Oswego with a group: Think about how many bedrooms you'll require, along with additional features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily refine your search to include all these options and more on Vrbo.
  • Traveling to Oswego with young kids: Travelling with young children can be quite a task. It's important to prioritize their comfort and safety, along with 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 fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo accommodations that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Oswego: If you're in search of vacation rentals that offer discounts 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 consider including amenities like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Oswego

Oswego, Indiana, is a delightful village ideal for a romantic getaway or an outdoor adventure. Surrounded by charming neighborhoods and serene bungalows, visitors can enjoy picturesque water views and the conveniences of city life. Stroll through downtown for a friendly atmosphere, perfect for family-friendly excursions or a relaxing day out. Whether you're seeking relaxation or adventure, Oswego offers a unique blend of experiences that will make your vacation truly memorable.

  • Syracuse: Syracuse is a charming city located 12.9km from Oswego, offering visitors an enticing blend of outdoor beauty and romantic scenery. The area is perfect for those seeking leisurely activities such as golfing at local courses or enjoying recreational areas. Nature lovers can explore nearby lakes and the stunning national state park, where the scenic dunes add to the picturesque landscape. Whether you’re looking for a serene picnic spot or a place to enjoy water activities, Syracuse provides an idyllic escape into nature.
  • Leesburg: Just 4.8km from Oswego, Leesburg is a quaint city that beckons tourists with its captivating outdoor experiences and scenic views. Here, you can partake in various recreational activities, including golfing and exploring beautiful parks. The local landscape is dotted with lakes and the expansive national state park, which features stunning dunes that enhance the area's natural charm. Leesburg is an excellent destination for a romantic getaway or a peaceful day spent in the embrace of nature.
  • North Webster: Located 8.0km from Oswego, North Webster is a delightful city that offers a wealth of outdoor adventures and picturesque scenery. This area is ideal for those looking to connect with nature through various activities like camping and hiking on local trails. The proximity to beautiful lakes and the national state park with its awe-inspiring dunes makes North Webster a must-visit for outdoor enthusiasts. Whether you're hiking through lush landscapes or enjoying a relaxing day at the campground, North Webster promises a memorable experience.

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 from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.2°F (-3.8°C)Light RainMostly CloudyLowAverage
February27.5°F (-2.5°C)Light RainMostly CloudyLowSlightly Low
March38.8°F (3.8°C)Light RainMostly CloudyLowSlightly Low
April48.7°F (9.3°C)Light RainMostly CloudyAverageSlightly Low
May60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
June69.4°F (20.8°C)Light RainMostly SunnyHighSlightly High
July72.5°F (22.5°C)Light RainMostly SunnyHighSlightly High
August70.9°F (21.6°C)Light RainMostly SunnyHighSlightly High
September64.9°F (18.3°C)Light RainMostly SunnyAverageAverage
October53.4°F (11.9°C)Light RainMostly SunnyAverageAverage
November40.8°F (4.9°C)Light RainMostly SunnyAverageAverage
December32.4°F (0.2°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is simple

Are you eager to save on your upcoming adventure? It's worth considering some flexibility with your travel dates, as prices can vary significantly. Additionally, opting for an extended stay often leads to substantial savings. To help you discover the perfect Vrbo property that fits your budget, take advantage of our filters, which allow you to sort by price, location, and type of vacation rental. We're here to assist you in finding the best options for your Canadian getaway!

Vrbo Trips: Planning made easy

Vrbo's unique Trip Board offers you a dedicated area to plan new trips, pick up right where you paused, or manage your travel arrangements. You can easily locate the properties you've saved or booked under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your Oswego getaway

Experience the unique character of Oswego with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. 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 hoping to discover attractions to see while you're in town? Venture out of your cozy vacation rental and experience everything that makes Oswego a fun spot to vacation. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • South Shore Golf Club (6.5 mi / 10.5 km)
  • Wawasee Golf Club (8.2 mi / 13.2 km)
  • Maxwelton Golf Club (8.5 mi / 13.7 km)
  • New Paris Speedway (12.3 mi / 19.8 km)
  • McCormick Creek Golf Course (13.9 mi / 22.4 km)

Exploring the natural features in Oswego

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Oswego is a great spot to appreciate mother nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Tippecanoe Lake (1.5 mi / 2.5 km)
  • Chapman Lakes (2.3 mi / 3.6 km)
  • Dewart Lake (3.7 mi / 6 km)
  • Big Barbee Lake (4.9 mi / 7.9 km)
  • Hidden Lake (5.3 mi / 8.5 km)
  • Webster Lake (5.6 mi / 9 km)

How to get to and around Oswego

Fly into Goshen, IN (GSH-Goshen Municipal), the closest airport, located 14.1 mi (22.7 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Fort Wayne Intl. Airport (FWA), which is 38.7 mi (62.3 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, Indiana, a popular area to stay is the charming downtown district. This vibrant neighbourhood offers a delightful mix of historic architecture and modern amenities, making it an ideal base for exploring the local culture. You'll find a variety of restaurants, cafes, and boutique shops just a short stroll away. A highlight of downtown Oswego is the picturesque Fox River, where you can enjoy scenic walks or picnics by the water.

Another excellent option is the area near the scenic parks, such as the popular Waubonsie Lake Park. This location not only provides access to lush green spaces for outdoor activities but also offers a peaceful retreat for those looking to unwind. The park features walking trails, picnic areas, and lovely views, making it superb for families and nature enthusiasts alike.
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.
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 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.
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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