Photo by Vin Lane-Kieltyka

Oshkosh holiday lettings

We found 838 holiday rentals — enter your dates for availability

Discover a selection of 308 homes, 13 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.

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

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.

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.

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

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.

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:

  • Pollock Community Water Park (1.8 mi / 2.9 km)
  • The Plaid Squirrel (12.4 mi / 19.9 km)
  • Larson's Famous Clydesdales (20.2 mi / 32.5 km)
  • Hughes Home Maid Chocolates (1.5 mi / 2.3 km)
  • Rushford Meadery and Winery (14.3 mi / 23 km)
  • Vines and Rushes Winery (17 mi / 27.3 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)
  • Ford Festival Park (4.7 mi / 7.6 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)

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?
When considering a holiday rental in Oshkosh, Wisconsin, the downtown area emerges as a fantastic option. This vibrant neighbourhood offers a charming blend of historic architecture and modern conveniences, making it a delightful place to explore. One of the main attractions is the Oshkosh Museum, which provides fascinating insights into the local history and culture. Additionally, the scenic banks of the Fox River are great for leisurely strolls or picnics, and you can often find community events taking place in the parks nearby.

Another appealing area is the waterfront along Lake Winnebago. Here, you can enjoy stunning views and access to various recreational activities. The local marina is a highlight for those who love boating or fishing, while the nearby parks are ideal for families looking to enjoy some outdoor fun. Both neighbourhoods offer a range of holiday rental properties, providing visitors with plenty of choices to suit their needs, whether it be a cosy apartment or a spacious family home.
How much does it cost to rent a holiday home in Oshkosh?
Prices for holiday rentals in Oshkosh 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 Oshkosh 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 Oshkosh holiday house rentals?
You can find great discounts on house rentals in Oshkosh 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.
Where are the best areas for renting a beach house in Oshkosh?
For renting a beach house in Oshkosh, the areas along the shores of Lake Winnebago are particularly appealing. The neighbourhoods near Menominee Park offer a lovely lakeside setting, where you can find properties with direct access to sandy beaches and scenic views of the water. Many of these rentals come equipped with amenities such as outdoor decks, barbecues, and spacious living areas, making them great for families or groups wanting to enjoy a relaxing lakeside holiday.

Additionally, the area around the Oshkosh Convention Centre provides convenient access to both the lake and local attractions. Here, you can discover charming waterfront homes that often feature private docks for boating enthusiasts, along with modern kitchens and comfortable furnishings. The proximity to parks and walking trails enhances the outdoor experience, allowing guests to fully enjoy the natural beauty of the surroundings.

For those who enjoy local culture, the downtown Oshkosh area is a short drive away, offering a vibrant setting with shops, restaurants, and events throughout the year. Rentals in this region often include amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay while being close to the lake's recreational activities.
Where are the best Oshkosh ski resort rentals?
For those seeking ski resort rentals near Oshkosh, Wisconsin, the closest ski area is in the nearby town of Fond du Lac, approximately a 30-minute drive away. In Fond du Lac, travellers can find various accommodations that cater to skiing enthusiasts. Many options include cozy cabins and lodges that provide easy access to the slopes at local ski areas. These properties often feature amenities such as fireplaces, hot tubs, and fully equipped kitchens, making them ideal for families and groups looking for a comfortable retreat after a day on the snow.

Additionally, the surrounding areas, including the scenic Kettle Moraine State Forest, offer opportunities for those interested in cross-country skiing and snowshoeing, with numerous trails to explore. Rentals in this region typically provide a warm and inviting atmosphere, with some properties boasting spacious living areas and outdoor patios for enjoying the winter landscape.
What is the most popular type of holiday rental accomodation in Oshkosh?
In Oshkosh, holiday houses are the most popular type of holiday rental, with around 596 available throughout the city. These homes often provide ample space, featuring multiple bedrooms, fully equipped kitchens, and outdoor areas such as patios or gardens, making them ideal for families or larger groups. Additionally, there are about 24 condos and 24 apartments, which tend to offer a more compact yet comfortable stay, often equipped with modern amenities such as Wi-Fi and laundry facilities. For those seeking a quaint experience, approximately 20 cottages are also available, typically located in scenic areas and offering a charming, rustic atmosphere.
Are there any family house rentals in Oshkosh?
In Oshkosh, Wisconsin, there are numerous family-friendly holiday rentals available, with around 105 options to choose from. The city is well-known for its welcoming atmosphere and proximity to various attractions, making it an excellent choice for families. Many properties offer spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play safely.

Visitors can explore nearby points of interest, such as the Oshkosh Public Museum, which provides insight into local history, or the scenic Lake Winnebago, great for outdoor activities like fishing and boating. Additionally, some rentals may include amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable and convenient stay for families.
Can I rent a holiday home with a pool or hot tub in Oshkosh?
In Oshkosh, Wisconsin, there are several holiday homes available for rent that feature pools and hot tubs, with around 14 options to choose from. This charming city, located on the shores of Lake Winnebago, offers a mix of residential and lakeside neighbourhoods where these properties can be found.

Travellers can expect amenities such as private swimming pools, hot tubs, spacious outdoor areas for relaxation, and fully equipped kitchens ideal for family meals or gatherings. Many rentals also provide additional comforts like air conditioning, laundry facilities, and easy access to local parks and the lake, enhancing the overall holiday experience.
Can I find long-stay holiday rentals in Oshkosh?
A long-stay holiday rental in Oshkosh 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 Oshkosh?
In Oshkosh, there are numerous pet-friendly house rentals available, with a total of 55 options for travellers seeking accommodations that welcome their furry companions. These holiday rentals often come equipped with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups.

The neighbourhoods around Lake Winnebago offer scenic views and plenty of outdoor activities, superb for pet owners. Nearby parks, such as the expansive Menominee Park, provide ample space for walks and playtime with pets, featuring trails and picnic areas. Additionally, the city has several dog-friendly cafes and shops, which further enhance the experience for visitors who want to explore the area with their pets.
Are there any remote work holiday rentals in Oshkosh?
In Oshkosh, Wisconsin, there are plenty of remote work holiday rentals available, with around 596 options to choose from. This city offers a variety of accommodations suiting remote workers, featuring amenities that make it easy to maintain productivity while enjoying a change of scenery. Most properties come equipped with high-speed Wi-Fi, dedicated workspaces like desks and comfortable chairs, and some even provide free internet access in rooms.

The downtown area of Oshkosh boasts charming historical buildings and is close to local cafes and restaurants, providing great spots for a break during work hours. Additionally, the nearby Fox River offers beautiful views and opportunities for outdoor activities, allowing for a refreshing escape after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oshkosh holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Oshkosh 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 Oshkosh?
In Oshkosh, popular rental amenities include kitchens, allowing guests to prepare their own meals, and onsite parking for convenience. Many properties also feature decks or patios, providing a lovely space to relax outdoors. Additionally, rentals often come equipped with coffee and tea makers for a morning boost, as well as blenders for those who enjoy smoothies or cooking.
When is the best time to visit Oshkosh for a holiday rental?
The peak season for visiting Oshkosh is during the vibrant summer months of June to August, with July being the most popular time for travellers. This period is ideal for those seeking outdoor adventures and lively community events, including the renowned EAA AirVenture Oshkosh, which draws aviation enthusiasts from around the world. The warm weather, with temperatures typically ranging from 20 to 30 degrees Celsius, makes it superb for exploring the beautiful lakes and parks, or enjoying a leisurely stroll along the scenic waterfront.

If you prefer a quieter experience, consider visiting Oshkosh in November. This month offers a unique charm, with fewer crowds and the opportunity to enjoy the picturesque autumn scenery. The crisp air and beautiful fall colours can make for a lovely backdrop while you explore local attractions at a more relaxed pace.

Ultimately, the best time to visit Oshkosh for a holiday rental depends on your interests.
How early should I book a Oshkosh holiday rental?
Book your Oshkosh 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 Oshkosh?
In Oshkosh, visitors can enjoy a variety of attractions that highlight the city's rich history and natural beauty. The Oshkosh Public Museum, located on Algoma Boulevard, offers fascinating exhibits on local history, including the area's Native American heritage and the impact of the lumber industry. Nearby, the historic district features charming architecture and the beautiful Riverside Park, where guests can stroll along the Fox River and enjoy the scenic views.

For those interested in aviation, the EAA Aviation Museum is a must-visit, showcasing an impressive collection of historic aircraft and offering interactive exhibits. Additionally, the Menominee Park provides a wonderful outdoor experience, complete with a zoo, picnic areas, and walking trails. The nearby Paine Art Centre and Gardens is another highlight, featuring stunning gardens and rotating art exhibitions in a historic mansion.
Can I change or cancel my Oshkosh home rental booking on Vrbo?
To find Oshkosh 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 Oshkosh 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