Photo by Vin Lane-Kieltyka

Oshkosh holiday lettings

We found 840 holiday rentals — enter your dates for availability

Discover a selection of 303 homes, 23 apartments and other holiday rentals in Oshkosh that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your stay with friends, family or just your pet, such as a garden and pool. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Oshkosh

Showing deals for:26 Sept - 3 Oct
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Why visit Oshkosh

  • Charming Downtown: Explore Oshkosh's vibrant downtown, filled with friendly locals and a welcoming atmosphere, perfect for leisurely strolls.
  • Beautiful Lakes: Enjoy the stunning scenery of the nearby lakes, ideal for romantic outings or family picnics.
  • Aviation Museums: Visit fascinating aviation museums that showcase the rich history of flight and aviation.
  • Outdoor Activities: Engage in a variety of outdoor adventures, from tranquil parks to exciting recreational options.
  • Quaint Accommodation: Choose from cosy cabins, charming cottages, and private vacation homes for a comfortable stay.

Popular types of accommodation in Oshkosh

If you're considering a getaway to Oshkosh, you're in for a treat! The most sought-after types of accommodation here include houses, charming cottages, and cosy cabins. Whether you're looking for rental homes or apartments, Oshkosh offers a variety of options to suit your needs. Enjoy transparency and savings as you explore the perfect place to unwind and create lasting memories in this delightful destination.

  • Houses: The top choice for holiday rentals in Oshkosh, offering a home-like atmosphere perfect for families or groups.
  • Cottages: A charming option for those seeking a quaint escape, ideal for peaceful retreats amidst nature.
  • Cabins: Popular among nature enthusiasts, these rustic lodgings provide a cosy and adventurous stay.
  • Apartments: Convenient and modern, apartments are perfect for couples or solo travellers wanting easy access to city amenities.
  • Condos: Offering a blend of comfort and luxury, condos are great for those desiring more space and upscale facilities.**

Top attractions in and around Oshkosh

Oshkosh, Wisconsin, is perfect for a romantic outdoor getaway, offering stunning scenery and a variety of attractions. Visitors can explore modern colleges and universities, fascinating aviation museums, and the beautiful lakes in the area. Whether you're travelling as a family, a couple, or in a group, Oshkosh provides a delightful mix of outdoor activities and cultural experiences that cater to all types of tourists.

  • EAA Aviation Museum: A fascinating aviation museum showcasing the history of flight with extensive exhibits, vintage aircraft, and interactive displays. This cultural hub offers a unique glimpse into aviation's past, making it a must-visit for enthusiasts and families alike.
  • Lake Winnebago: A stunning lake located 3.1km from Oshkosh, perfect for outdoor activities. Enjoy picturesque scenery, sandy beaches, and opportunities for romantic strolls or picnics amid nature's beauty.
  • University of Wisconsin-Oshkosh: A modern college campus in the heart of Oshkosh, known for its vibrant atmosphere and engaging community. Explore its beautiful grounds, impressive facilities, and various student activities.

Things to do recommended for couples

Seeking a romantic getaway in Oshkosh? Visit Vines and Rushes Winery, 10.6km away, for a delightful experience filled with wine and charm. Alternatively, Rushford Meadery and Winery, located 8.7km from Oshkosh, offers a magical atmosphere perfect for couples to unwind together.

Things to do recommended for families

Families visiting Oshkosh can enjoy exciting events at the Menominee Nation Arena, splash about at Pollock Community Water Park, and indulge in delightful treats at Hughes Home Maid Chocolates, ensuring a fun-filled experience for all ages in this charming town.

Things to do recommended for groups

Groups visiting Oshkosh can indulge in retail therapy at The Outlet Shoppes, savour local produce at the Saturday Farmers Market, and enjoy a round of golf at the scenic Bridgewood Golf Course, located 6.8km away, perfect for outdoor enthusiasts.

Booking with Vrbo is simple

Are you hoping to cut costs on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of holiday rental.

Where to stay in and around Oshkosh

Oshkosh, Wisconsin, offers a delightful blend of outdoor adventures and charming scenery, making it an ideal destination for a romantic getaway or a family-friendly holiday. Explore the vibrant downtown, where friendly locals and a welcoming atmosphere await. Nearby attractions provide a wealth of experiences, from tranquil parks to bustling neighbourhoods, ensuring a memorable visit. Discover the allure of this quaint city and its surrounding regions, perfect for relaxation and exploration.

  • Black Wolf: Nestled in the vicinity of Oshkosh, Black Wolf is a charming village that offers a delightful escape for those seeking outdoor adventures and picturesque scenery. This area is perfect for couples looking for a romantic getaway. Visitors can enjoy various activities, including exploring the local recreational area and spending a fun-filled day at the water park. Notable attractions nearby include a scenic lake, an intriguing aviation museum, and a lively stadium, which all contribute to the village's welcoming atmosphere.
  • Winnebago: Located a mere 2.5km from Oshkosh, Winnebago is a vibrant city that entices travellers with its splendid outdoor experiences and stunning landscapes. This city is particularly popular for skiing enthusiasts, boasting access to excellent ski resorts and recreational areas. Visitors can immerse themselves in the natural beauty of the region, while also enjoying local events at the conference venue. The nearby lake and river provide additional opportunities for relaxation and adventure, making Winnebago a fantastic destination for those looking to connect with nature.
  • Neenah: Situated 7.5km away from Oshkosh, Neenah is a picturesque city that captivates visitors with its lovely outdoor spaces and shopping opportunities. The city features a variety of recreational areas and shopping centres, making it a great spot for both relaxation and retail therapy. Sports fans will appreciate the local stadium and sports facilities, which host a range of events throughout the year. With its scenic lake and charming atmosphere, Neenah offers a delightful blend of leisure and entertainment, making it a must-visit during your holiday.

Best time to go to Oshkosh

If you're planning a trip to Oshkosh, 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 October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January18.0°F (-7.8°C)No Rain (Dry)Mostly CloudyAverageSlightly Low
February19.2°F (-7.1°C)No Rain (Dry)Mostly CloudyAverageSlightly Low
March32.0°F (0.0°C)Light RainMostly CloudyAverageSlightly Low
April42.6°F (5.9°C)Light RainMostly CloudySlightly HighAverage
May55.6°F (13.1°C)Light RainMostly SunnyAverageAverage
June65.7°F (18.7°C)Light RainMostly SunnySlightly HighSlightly High
July70.9°F (21.6°C)Light RainMostly SunnySlightly HighSlightly High
August69.3°F (20.7°C)Light RainMostly SunnyAverageSlightly High
September62.1°F (16.7°C)Light RainMostly SunnyAverageAverage
October49.5°F (9.7°C)Light RainMostly SunnySlightly LowAverage
November36.9°F (2.7°C)Light RainMostly SunnySlightly LowAverage
December25.9°F (-3.4°C)Light RainMostly CloudySlightly LowAverage

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

If you’re travelling with a group, as a family, with pets, or seeking extended stays, be sure to apply the appropriate filters to meet your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Oshkosh with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Oshkosh with young kids: Going on holiday with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Oshkosh: For many, a family holiday wouldn’t be the same without their furry companion by their side. If this resonates with you, be sure to explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at ease.
  • Planning for a long term stay visiting Oshkosh: If you're seeking holiday rentals with discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private swimming pool to your search as well.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new holidays, progress with your travel arrangements, or manage your bookings effectively. You’ll find that your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Head to the arty city of Oshkosh

Take a holiday to Oshkosh and enjoy the area's art galleries, museums and festivals. This city's shopping, sporting events and zoo draw many visitors. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Oshkosh

Are you hoping to discover attractions to see during your stay? Venture out of your cosy holiday rental and check out everything that makes Oshkosh a one-of-a-kind holiday spot. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Larson's Famous Clydesdales (20.2 mi / 32.5 km)
  • Pollock Community Water Park (1.8 mi / 2.9 km)
  • Bridgewood Golf Course (10.6 mi / 17.1 km)
  • Hickory Hills Country Club (17.3 mi / 27.9 km)
  • Chaska Golf Course (17.5 mi / 28.2 km)
  • Hughes Home Maid Chocolates (1.5 mi / 2.3 km)

Exploring the natural features in Oshkosh

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Oshkosh is a great place to get outside. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Paine Art Center and Gardens (1.4 mi / 2.3 km)
  • Lake Winnebago (5.2 mi / 8.3 km)
  • Lakeside Park (16.1 mi / 25.9 km)
  • Pierce Park (17.1 mi / 27.5 km)
  • Lake Poygan (17.4 mi / 28 km)
  • Erb Park (19.1 mi / 30.7 km)

Travelling to and around Oshkosh

Fly into Appleton, WI (ATW-Appleton Intl.), the closest airport, located 16.7 mi (26.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Fond du Lac, WI (FLD-Fond du Lac County), which is 17.5 mi (28.1 km) away.

Frequently asked questions

What is the best area to stay in Oshkosh when booking a holiday rental?
Among the most sought-after neighbourhoods to find an Oshkosh holiday home is Black Wolf. When you book your stay with Vrbo, you will have the whole place to yourselves. So you don't have to share it with anyone except for your group.
What is the most popular type of holiday rental accommodation in Oshkosh?
Houses are the most popular style of holiday rental in Oshkosh, according to our data. Even if you have a different idea about what you'd like, Vrbo has holiday homes in a variety of shapes and sizes. Filter our options to find your perfect fit.
How much does it cost to rent a holiday rental in Oshkosh?
The average price for a holiday rental in Oshkosh depends on several factors, such as property type, length of stay and time of year. Whether you're thinking about a sprawling villa with a pool or a comfy cabin perfect for just you and the kids, just enter your dates of travel to see stays with unbeatable value.
How much does it cost to rent a beach house in Oshkosh?
Prices for beach houses in Oshkosh may vary depending on the size and style of the property and when you plan to travel. Just enter your travel dates into Vrbo and the number of guests to view available options and prices. From there you can use our filter tool to refine your search by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday rentals in Oshkosh?
Yes. You'll have a choice of 40 holiday rentals that allow pets in Oshkosh. Plenty of our pet-friendly holiday rentals even come with a backyard for your fur baby to play in, complimentary treats, special dog beds and proximity to parks. Apply the "Pets allowed" filter to find a pad that'll set tails wagging on Vrbo.
Can I rent a house with a pool in Oshkosh?
Check the "pool" box in our handy filter tool and choose from six houses with private pools in Oshkosh on Vrbo. Lazy soak or races and ball games? How you spend your leisure time is up to you when your holiday home boasts its own swimming pool.
What are popular rental amenities in Oshkosh?
The most popular rental amenities people search for in Oshkosh include a nearby waterfront, a lake view and a firepit. Whether you're going on holiday with your besties, family or even pets, Vrbo holiday rentals provide the best amenities for making epic memories with the people you cherish the most.
Are there large group holiday rentals in Oshkosh?
With 10 properties that can host 10 people or more in Oshkosh, you don't have to keep anyone off the invite list. From family holidays to special events like weddings and birthday parties, Vrbo can help you find a large group rental that fits the occasion.
Are there holiday rentals in Oshkosh that welcome kids?
Bring the entire family together for a fun-filled adventure in Oshkosh at one of our 39 family-friendly holiday homes. These stays provide amenities that are suitable for getaways with children, including dining rooms, living rooms and private pools. Just click on the "Properties good for families" filter box and decide on your favourite.
What are the top attractions for families in Oshkosh?
You'll find loads of amazing things to see and do with the family in Oshkosh, such as:

  • EAA Aviation Museum
  • Menominee Park
  • Pollock Community Water Park

Are there one-bedroom holiday rentals in Oshkosh?
Yes, Oshkosh has two one-bedroom rentals on offer. Usually situated in well-regarded areas thanks to their smaller size, a one-bedroom holiday property is great if you're travelling with your partner or a pal. And with home comforts like wireless internet and more privacy than a standard hotel, you'll be able to kick back and relax while enjoying this exciting destination.
Can I find two-bedroom holiday rentals in Oshkosh?
You can select from 12 two-bedroom holiday rentals in Oshkosh. Put your little ones in the second room or maybe fill it with a couple of your favourite people. There's a comfy spot for whoever's fortunate enough to come along for the ride.
Are there holiday rentals with WiFi in Oshkosh?
You can choose from 12 holiday rentals with WiFi in Oshkosh. If you'd like to disconnect from the world during your trip, but still need to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Oshkosh?
Pick your dates and then use our filters to search for holiday rentals with ac in Oshkosh on Vrbo. With 38 air-conditioned properties on offer here, you can enjoy a cool and comfortable stay.
How old do you have to be to rent a holiday rental in Oshkosh?
The minimum age allowed can differ across properties on Vrbo, so be sure to look at the rules of the holiday rental in Oshkosh you're considering. But usually, it's 16, 18 or 21.
How long can I rent a holiday rental in Oshkosh for?
It really depends on the Oshkosh property. To see all available options offering extended stays, just type your dates and guest number into Vrbo. You can enjoy having the whole property to yourself, along with home comforts such as a kitchen, air conditioning and outdoor spaces where the kids can run and play. Keep your eyes peeled for long-term stays that offer weekly or monthly discounts.

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