Holiday rentals in Oshkosh

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Top-rated holiday rentals in Oshkosh

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
The A-frame cabin is framed by lush greenery and colorful landscaping. A welcoming pathway leads to the entrance, featuring a spacious deck. The cabin's dark exterior contrasts with the surrounding trees, creating a serene and private atmosphere.
Cabin in Elkhart Lake
4.99 out of 5 average rating, 335 reviews

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

Top guest favourite
Home in Appleton
5 out of 5 average rating, 155 reviews

Appleton Wooded Oasis - Hot Tub-6 Star Hospitality

Relax and enjoy in a beautiful scenic home conveniently located in a quiet wooded neighborhood in Appleton. It has all the elements of being your get away from home. Nearly 3,000 sq. ft. Guests have access to all living areas, modern kitchen, full mason fireplace, vaulted ceilings, large deck and hot tub. Enjoy the backyard with a spacious deck, 7 person hot tub and outdoor fire pit. Five min. from Airport, Downtown, 25 min. to Lambeau and 20 min. to EAA. Includes coffee and breakfast.

Top guest favourite
A wooden deck overlooks Sawyer Creek, featuring two metal chairs with floral cushions positioned around a small fire table. Lush greenery surrounds the area, and a dock extends into the water, providing a serene view of the natural setting.
Home in Oshkosh
5 out of 5 average rating, 64 reviews

Fenced Yard; Waterfront; Dock, Cozy & Refreshing

Take it easy at this unique and tranquil getaway. Located on Sawyer Creek; enjoy peaceful views in a quiet neighborhood. Privacy is yours with a fenced in yard & attached 2 car garage. Comfortable 2 bedrooms with Queen beds & a fully stocked kitchen, outdoor grill, 55 in Smart TV and dedicated desk area. Propane firepit, patio table & 2 kayaks, washer & dryer. Close to Wiowash Trail, resturants, UW-Oshkosh and Oshkosh Corp headquarters. EAA grounds is a short 12 minute drive. Dog friendly.

Top guest favourite
Home in Oshkosh
4.99 out of 5 average rating, 138 reviews

LakeHome! Relaxing! Cozy! Amazing Sunsets!

On the shore of Lake Butte Des Morts Longer stays welcome!!! Awesome Lake view private pier for fishing/relaxing(we do not allow anything to be tied up to pier at any time) Beautiful Sunsets Gas fireplace Shopping/restaurants/etc Near EAA Approx. 40 miles from Lambeau Field fire pit grill Lake view Bedroom,Living Room,Dining area Near by Wiouwash trail for hiking, biking, etc.. Kitchen space for cooking. Washer/dryer Larger 1 bedroom /Queen Sleep Number mattress Off street parking

Guest favourite
A log home with a wooden exterior is surrounded by lush greenery. The front porch is adorned with a small blue umbrella and features a set of steps leading to the entrance. Gravel driveway and flower beds enhance the welcoming ambiance of the property.
Home in Oshkosh
4.87 out of 5 average rating, 204 reviews

Go and Go

Cozy 2 bedroom Log home. Can sleep 4-6. Across the street from Lake Winnebago. Short walk to park, zoo and boat landing. 6.5 miles to EAA grounds. Off street parking. Close to shopping, restaurants and downtown Oshkosh. Great rental for Air Show, Book now and bring your boat, jet ski, trailer, and fishing gear or just go sightseeing, dining and relaxing. Full kitchen, New Bath. Very comfortable with a great location. Perfect place to stay for family with students at UWO. Book now!

Top guest favourite
Cabin in Cascade
5 out of 5 average rating, 241 reviews

sauna and hot tub on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Top guest favourite
The cottage features a long, metal-roofed exterior with gray siding and contrasting purple shutters. Lush greenery surrounds the home, including decorative flower beds. A paved pathway leads to the entrance, highlighting the spacious yard. Sunlight enhances the bright and welcoming appearance.
Guest house in Oshkosh
4.95 out of 5 average rating, 195 reviews

Cottage on Lake Winnebago

Furnished Cottage on Lake Winnebago with beautiful sunrises. 1 bedroom with queen bed. There is plenty of space for air mattresses in common areas. 1 queen air mattress available. One bath, full kitchen fully stocked with dining area, bring your own food to prepare. Bring your water toys or boat, launch nearby and dock access in warmer months with great fishing. Winter months, bring your snowmobile, trails nearby. Great ice fishing when lake is frozen and ice is safe.

Top guest favourite
A two-story home is presented with dark green siding, framed by manicured lawns and established trees. A paved walkway leads to the front door, which is flanked by windowed entries. Clear skies above add to the home's inviting exterior appearance.
Home in Oshkosh
4.9 out of 5 average rating, 107 reviews

Shorehaven Lakehouse

Welcome to the Shorehaven Lake House! Perfect for a couples retreat, an outing for the entire family, or those in town for any of Oshkosh and the surrounding cities many events! Have the ultimate Wisconsin getaway by escaping to this beautifully renovated Lake Butte des Morts home that comfortably sleeps 6. This home provides beautiful sunsets and sunrises over the lake and a quiet neighborhood for your escape! Please let us know if you have any questions!

Guest favourite
A spacious dining area is illuminated by natural light from large windows. A wooden table with six chairs is centered in the room. Decorative items, including wall art and a wreath, are displayed on the walls, contributing to the charming ambiance.
Home in Oshkosh
4.91 out of 5 average rating, 242 reviews

Charming Spacious 2BDR by Downtown/Menominee/Lake

This historic and charming home is located just one block away from Menominee Park and Lake Winnebago. Menominee parks offers amusement rides, the Zoo, asphalt trails, boat tie ups, casting dock, historical interest, fishing, ice rink, picnic areas, large playgrounds, baseball fields, soccer fields, tennis/ pickle ball courts, and volley ball courts. The home boasts a lot of character and has all the amenities to make your stay comfortable and memorable.

Guest favourite
The exterior of a two-story house is shown, featuring a porch and a well-maintained lawn. Large windows are visible, offering natural light to the interior. Surrounding trees provide shade, and a pathway leads to the entrance, enhancing accessibility.
Flat in Oshkosh
4.86 out of 5 average rating, 250 reviews

No Cleaning Fees! 2 Bedroom Apartment By The Lake

We’re transparent with our pricing, that’s why we don’t have cleaning fees! The price you see is the price you pay (local taxes still apply). Come stay near the heart of Oshkosh - you’ll be on the second floor with views of Lake Winnebago. If you need anything during your stay we live on-site and are only a message away. Don’t worry though, the units are completely separated so you’ll have all the privacy you desire during your stay.

Guest favourite
An open living space features warm wooden beams and a mix of modern and rustic decor. A comfortable sofa and armchair are arranged around a coffee table, while a dining area accommodates six. Natural light enters through large windows, complemented by a vintage map on the wall.
Cabin in Winneconne
4.97 out of 5 average rating, 313 reviews

Barndominium: Goats, Hot Tub, Forest & River

The Cloverland Barndominium is a thoughtfully renovated 100-year-old barn sitting on 5+ private acres of forest to explore next to a river. You'll share the land with friendly goats that you can watch from right outside your window! Outside you'll enjoy walking the trails, feeding the animals, taking the canoe down the river, making a fire in the fire pit, and exploring the forest. Escape the busy world and reset!

Top guest favourite
A cozy sleeping area contains two full-size beds adorned with warm-colored bedding. Nightstands with lamps are placed beside each bed. A comfortable chair sits in the corner, and two windows allow natural light to illuminate the room. Decorative rugs cover the laminate flooring.
Flat in Oshkosh
4.91 out of 5 average rating, 302 reviews

Rosie's Place A

Hello and Welcome! Rosie's place A features a cozy newly renovated clean furnished upper apartment. Very close to everything in Oshkosh. Great for business travelers, vacationers and visiting University of Oshkosh and Hospital families. Breakfast items, fruit, coffee, tea, soda, water & snacks included. Private parking behind the house. Door code will be provided to enter. No minimum stay!

Popular amenities for Oshkosh holiday rentals

When is the best time to visit Oshkosh?

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Avg. price$233 SGD$234 SGD$216 SGD$342 SGD$255 SGD$260 SGD$616 SGD$318 SGD$254 SGD$240 SGD$234 SGD$227 SGD
Avg. temp-8°C-6°C0°C7°C14°C19°C21°C20°C16°C9°C2°C-4°C

Frequently Asked Questions

  • What are the best places to stay in Oshkosh?

    Many guests prefer staying near the lakefront or in the historic downtown for easy access to shops, dining, and cultural sites. Residential neighborhoods also have peaceful options with local character.

  • What are the best things to do in Oshkosh with kids?

    Families often explore the hands-on exhibits at local discovery centers, visit the zoo, or enjoy playgrounds in city parks. Waterfront paths are also popular for kid-friendly walks and picnics.

  • What are some of the best things to do in Oshkosh?

    Oshkosh has art galleries, family-friendly museums, and boating or kayak outings on its waterways. Visitors often explore downtown shops and take part in community events throughout the year.

  • How is the weather in Oshkosh?

    Oshkosh has cold, snowy winters around 10–30°F (-12–-1°C), and warm summers with highs near 80°F (27°C). Spring and autumn bring milder temperatures and scenic changes, so layered clothing is useful year-round.

  • When is the best time to visit Oshkosh?

    Late spring through early autumn is often recommended, with comfortable temperatures around 60–80°F (16–27°C) and several recurring festivals. This season brings opportunities for outdoor exploration and lakeside events.

  • What are the best places to visit in Oshkosh?

    Explore Oshkosh Public Museum, Paine Art Center and Gardens, and Menominee Park for natural beauty and activities. The downtown area has historic buildings, galleries, and locally owned shops.

  • What are some hiking trails in Oshkosh?

    Oshkosh has trails in public parks, nature preserves, and along its lakefront, providing options for leisurely strolls or birdwatching. Boardwalks and woodland paths suit a variety of interests and abilities.

  • What are some family activities we can do in Oshkosh?

    Oshkosh has hands-on museums, local parks for outdoor adventures, and a zoo where children can explore animal exhibits. The area frequently suggests waterfront activities and family-friendly discovery centers.

  • What are some of the best day trip ideas from Oshkosh?

    Popular day trip ideas include exploring local state parks, nearby botanical gardens, and communities with historic downtowns known for antiques and artisan shops. Scenic trails and waterfront nature preserves are often suggested for those seeking outdoor experiences.

  • Are there any pet friendly accommodations available in Oshkosh?

    Oshkosh has pet-friendly stays, especially around the downtown and lakefront neighborhoods. Many hosts welcome pets, and nearby parks make it easy to explore the outdoors with your companion.

  • What are some local tips for visiting Oshkosh?

    Locals often suggest packing layers, as weather can shift from cool mornings to warmer afternoons. Exploring the waterfront is a favorite, and enjoying seasonal produce at farmers markets helps visitors experience the regional flavors.

  • What is Oshkosh known for?

    Oshkosh is known for its aviation heritage, vibrant lakeside culture, and historic downtown. The city frequently hosts renowned air shows and fosters a tradition of community arts and local festivals.

  • What are the best hidden gems to explore in Oshkosh?

    Discover locally curated art spaces, tucked-away coffee shops, and peaceful nature preserves around Oshkosh. Community gardens and lesser-known trails offer quieter moments away from busier waterfront spots.

  • What are the best foods to try in Oshkosh?

    Classic Wisconsin flavors are frequently suggested, such as cheese curds, locally prepared fish dishes, and Friday night fish fries. Artisan bakeries and seasonal produce can also be found at farmers markets around the city.

  • What should I bring for a trip to Oshkosh?

    Pack layers to stay comfortable through fluctuating temperatures, a waterproof jacket for potential rain, and comfortable walking shoes for exploring city parks or lakefront paths. In summer, sunglasses and sun protection are often helpful.

  • What is the nightlife in Oshkosh like?

    Oshkosh has a casual nightlife scene, with locally-owned pubs, live music venues, and spots for late-night bites around the downtown area. Many evenings focus on music, conversation, and welcoming atmospheres.

  • What are the most popular events or festivals in Oshkosh?

    EAA AirVenture Oshkosh is a world-renowned aviation event drawing enthusiasts annually, while summer concerts and local art fairs animate the city during festival season. Winter brings holiday markets and themed celebrations.

  • Are there family friendly vacation rentals in Oshkosh?

    Oshkosh has family-friendly vacation rentals in residential neighborhoods, near the lakefront, and close to parks. Many homes have amenities suited for group stays and easy access to kid-friendly attractions.

Quick stats about holiday rentals in Oshkosh

  • Total holiday rentals

    Explore 830 holiday rentals in Oshkosh

  • Nightly prices starting at

    Oshkosh holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 8,920 verified reviews to help you choose

  • Family-friendly holiday rentals

    660 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 220 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    350 properties have a dedicated workspace

  • Wifi availability

    810 of Oshkosh holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Oshkosh rentals

  • 4.9 Average rating

    Oshkosh stays are highly rated by guests – averaging 4.9 out of 5!

Destinations to explore

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  5. Oshkosh