Oshkosh holiday rentals

We found 858 holiday rentals — enter your dates for availability
Discover a selection of 319 homes, 14 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:30 Oct - 6 Nov

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Why visit Oshkosh

  • AirVenture Festival: Experience the world-renowned aviation event showcasing innovative aircraft and engaging displays.
  • Urban & Scenic Blend: Enjoy a mix of vibrant downtown life and tranquil outdoor retreats, ideal for leisurely strolls.
  • Local Heritage: Discover the city's rich history through its museums, parks, and cultural landmarks.
  • Riverside Walks: Delight in scenic river walks that offer both relaxation and picturesque views.
  • Family & Romantic Getaways: Enjoy diverse attractions suitable for families and couples seeking a memorable escape.

Popular types of accommodation in Oshkosh

Welcome to Oshkosh, Wisconsin, a city rich in heritage and charm. Discover comfortable accommodations, including private holiday homes, cottages, and cabins, perfect for a memorable stay. Explore local attractions like museums, parks, and scenic river walks. Enjoy the best Oshkosh accommodation as you immerse yourself in its unique blend of history and modern comforts.

  • Private Holiday Homes: Enjoy the luxury of a self-catered retreat, offering privacy and space for families or groups.
  • Cottages: Experience a quaint, countryside dwelling ideal for a traditional British getaway.
  • Cabins: Embrace a rustic escape in cosy woodland lodgings perfect for nature enthusiasts.
  • Apartments: Choose urban comfort with modern amenities, suitable for shorter stays or city breaks.
  • Condos: Revel in contemporary living spaces, offering both style and convenience for your visit.**

Top attractions in and around Oshkosh

Oshkosh, Wisconsin, offers a delightful mix of outdoor activities, scenic lakes, and urban parks perfect for a romantic holiday. Visitors can immerse themselves in local culture at aviation museums and enjoy the vibrant atmosphere of events like the renowned EAA AirVenture Oshkosh. This charming city provides plenty of opportunities for leisurely exploration and memorable experiences, ensuring an enriching getaway for every traveller.

  • EAA Aviation Museum: This museum showcases the rich history of aviation with interactive exhibits, vintage aircraft, and educational programs, making it a must-visit for aviation enthusiasts and families alike.
  • Lake Winnebago: A picturesque destination, Lake Winnebago offers stunning scenery, sandy beaches, and various outdoor activities perfect for a romantic getaway or a family picnic.
  • Hearthstone Historic House Museum: Step back in time at this beautifully preserved Victorian home, featuring original furnishings and fascinating stories that highlight the region's cultural heritage.

Things to do recommended for couples

Oshkosh offers charming riverside walks and intimate dining at local bistros. Enjoy a sunset cruise on Lake Winnebago or explore the enchanting gardens at the Paine Art Center. For a unique experience, visit a local winery for a tasting session, perfect for couples seeking romance.

Things to do recommended for families

Families will delight in the interactive exhibits at the Oshkosh Public Museum, explore the hands-on activities at the EAA Aviation Museum, and enjoy outdoor fun at Menominee Park, complete with a zoo and playground, ensuring a memorable holiday for all ages.

Things to do recommended for groups

Discover Oshkosh with your group by exploring its local attractions and enjoying activities tailored for travellers. Visit vibrant markets, savour regional delicacies and take part in community events, all while immersing in the distinct charm of this Wisconsin town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

Whether you’re journeying with a group, travelling as a family, accompanied by your pets, or seeking extended stays, be sure to apply the appropriate filters. Here are some Stayz booking suggestions for you.

  • Traveling to Oshkosh with a group: Consider how many bedrooms you'll require, in addition to features like a fully-equipped kitchen or an outdoor area suitable for group get-togethers. Luckily, you can refine your search for all these options, and more, on Stayz.
  • Traveling to Oshkosh with young kids: Traveling with young children can present its difficulties. It is important to prioritise their comfort and safety, as well as ensure that appropriate amenities, like a private swimming pool, are available. Additionally, it is wise to consider how close you are to family-friendly attractions.
  • Taking your pets with you to Oshkosh: For many, a family holiday is simply not complete without the presence of their four-legged companion. If this resonates with you, then explore Stayz properties that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Oshkosh: If you are seeking holiday lets with offers for stays of a month or more, you've come to the right destination. By applying the appropriate filter, you can effortlessly locate and secure savings on monthly lets. You might also want to consider including options such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Oshkosh

Oshkosh, Wisconsin offers a charming blend of urban and scenic delights. Explore the vibrant downtown for lively experiences, stroll through quaint neighbourhoods, and enjoy peaceful retreats. Ideal for family excursions and romantic getaways, the city promises a friendly atmosphere with plenty of outdoor adventures and cultural attractions, ensuring a memorable visit for every traveller.

  • Neenah: Neenah, a vibrant city situated 19km from Oshkosh, offers a delightful blend of natural landscapes and urban conveniences. Visitors are drawn by its scenic outdoor settings and romantic ambience, ideal for leisurely strolls and memorable experiences. The area boasts a variety of shopping centres and malls, as well as a recreational area perfect for a day out. Notable landmarks include a picturesque lake, a well-equipped sports facility stadium, and an aviation museum that adds a unique historical flavour to your visit.
  • Black Wolf: Nestled within the vicinity of Oshkosh, Black Wolf is a charming village that promises an enchanting outdoor experience with breathtaking scenery. The village is renowned for its recreational areas and golf courses, ideal for those seeking a blend of relaxation and invigorating activity. Local attractions such as a serene lake, a fascinating aviation museum, and a sports facility stadium further enhance the appeal of this quaint locale.
  • Harbor Springs: Located 13km from Oshkosh, Harbor Springs is a picturesque village that captures the essence of a delightful outdoor retreat. Its scenic landscapes and romantic settings make it a perfect destination for those eager to explore nature. The area offers recreational facilities, educational venues, and golf courses, providing a variety of leisure options. Key attractions include a tranquil lake, an urban park, and a flowing river, each promising a unique and refreshing experience.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January18.0°F (-7.8°C)No Rain (Dry)Mostly CloudyAverageAverage
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 HighSlightly Low
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 Stayz is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a significant difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Stayz property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board provides a dedicated area for you to plan new journeys, refine your existing arrangements, or assess and manage your bookings. The properties you have saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/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)
  • Larson's Famous Clydesdales (20.2 mi / 32.5 km)
  • The Plaid Squirrel (12.4 mi / 19.9 km)
  • Vines and Rushes Winery (17 mi / 27.3 km)
  • Hickory Hills Country Club (17.3 mi / 27.9 km)
  • Chaska Golf Course (17.5 mi / 28.2 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 home?
Among the most sought-after neighbourhoods to find an Oshkosh holiday home is Black Wolf. When you book your stay with Stayz, 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 home accommodation in Oshkosh?
Houses are the most popular style of holiday home in Oshkosh, according to our data. Even if you have a different idea about what you'd like, Stayz 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 home in Oshkosh?
The average price for a holiday home 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 Stayz 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 homes in Oshkosh?
Yes. You'll have a choice of 40 holiday homes that allow pets in Oshkosh. Plenty of our pet-friendly holiday homes 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 Stayz.
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 Stayz. 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 home amenities in Oshkosh?
The most popular home 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, Stayz holiday homes provide the best amenities for making epic memories with the people you cherish the most.
Are there large group holiday homes 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, Stayz can help you find a large group home that fits the occasion.
Are there holiday homes 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 homes in Oshkosh?
Yes, Oshkosh has two one-bedroom homes 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 homes in Oshkosh?
You can select from 12 two-bedroom holiday homes 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 homes with WiFi in Oshkosh?
You can choose from 12 holiday homes 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 Stayz.
How can I find holiday homes with air conditioning in Oshkosh?
Pick your dates and then use our filters to search for holiday homes with ac in Oshkosh on Stayz. 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 home in Oshkosh?
The minimum age allowed can differ across properties on Stayz, so be sure to look at the rules of the holiday home in Oshkosh you're considering. But usually, it's 16, 18 or 21.
How long can I rent a holiday home 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 Stayz. 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.