Holiday rentals in Oshkosh

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Top-rated holiday rentals in Oshkosh

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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, 57 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.

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
4.86 out of 5 average rating, 197 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
The exterior of a cabin is depicted, featuring large windows framed by wood. Warm light emanates from within, revealing a cozy interior with a lamp and seating. Snow covers the ground, and icicles hang from the roof, creating a serene winter scene.
Cabin in New London
4.99 out of 5 average rating, 100 reviews

Secluded Cabin with Sauna

Place yourself in nature. Put down your phone and pick up a book. Clear your mind, focus on your breath, connect with your inner self. Sleep like you’ve never slept before accompanied only by the sound of owls and wind in the pines. The Belden Farm offers land that is a true retreat. Enjoy the privacy and quiet of our cabin in the woods. Extensive, well-maintained trails for hiking, skiing or Fattire biking lead you through towering hardwoods, cathedral white pines, and golden meadows.

Top guest favourite
A lush green lawn extends towards the lake, flanked by two large trees. Two wooden Adirondack chairs provide a comfortable seating area, facing the water. The serene lake view stretches into the distance, with a small boathouse visible nearby.
Home in Oshkosh
4.99 out of 5 average rating, 134 reviews

Cozy Relaxing Lake Home with spectacular sunsets!

Located on the shore of Lake Butte Des Morts Yard,pier in summer.sorry we do not allow anything to be tied up to pier,solo fire pit, grill,seating SUNSETS Lake view Bedroom,Living Room,Dining area Close to Wiouwash trail for hiking, biking,snowmobiling Approx. 40 miles to Lambeau Field Close to EAA Restaurants Shopping Gas fireplace in Living / dining room with a desk Kitchen with space for cooking. Washer/dryer Larger 1 bedroom /Queen Sleep Number mattress Off street parking

Guest favourite
A charming dining area features a large round table surrounded by wooden chairs, set against a backdrop of eclectic mirrors and wall decor. Natural light streams through the windows, illuminating the rustic elements and adjoining open kitchen area.
Home in Green Bay
4.93 out of 5 average rating, 102 reviews

Charming 1870s Downtown Loft

Like your favorite cup of coffee, this sunlit haven energizes and comforts. Just steps from downtown's vibrant pulse, this thoughtfully restored 1870s duplex is crafted for connection, creativity, and relaxation. Work under high ceilings bathed in natural light, or gather with friends in the spacious, open kitchen and dining area. Modern amenities ensure a home-like experience in a space that seamlessly combines the warmth of history with the ease of modern living.

Top 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, 232 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.

Top guest favourite
A relaxing living area features a stone fireplace as its focal point. Comfortable seating options, including a leather chair and a spacious sofa, are arranged around a rustic coffee table. Large windows allow natural light to fill the space, with glimpses of the surrounding scenery.
Cottage in Fond du Lac
4.99 out of 5 average rating, 289 reviews

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

Top guest favourite
An open concept living area features a modern kitchen with stainless steel appliances and a marble countertop. A round dining table with upholstered chairs complements the sleek bar stools at the kitchen island. Light wood flooring enhances the spacious feel of the room.
Home in Appleton
4.96 out of 5 average rating, 200 reviews

Modern, Freshly Renovated House - Great Location

-Historic residential district near downtown, Lawrence University, the Performing Arts Center, Mile of Music and more - great location but still VERY quiet area. -30 minutes to Green Bay and Oshkosh -3 season porch -New deck overlooking wooded backyard -Safe, well established neighborhood with tree-lined streets and beautiful parks -Need more space or traveling with friends? Click Visit our profile to see our additional 5★ Appleton properties

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, 229 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.

Top guest favourite
The dining area features a long wooden table surrounded by metal stools. Natural light enters through multiple windows with classic blinds, highlighting the rich wood accents and flooring. A modern light fixture hangs above the table, enhancing the room's inviting character.
Home in Oshkosh
4.85 out of 5 average rating, 111 reviews

Jackson Farmhouse

Perfect for a big group! Our beautifully restored 100 YEARD OLD farm house is located on Jackson St in Oshkosh giving you quick and easy access to highway 41! ** this home is old and has sloping floors ** The easy in and out driveway can hold at lease 6 cars if needed during your stay at our comfortable property. After a long day of whatever you may be in town for you'll be able to relax in your own piece of country!

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
4.92 out of 5 average rating, 290 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!

Superhost
The home exterior is characterized by a gray siding, complemented by a steep roof and multiple windows. A welcoming front porch is accessed by a set of stairs. Colorful flower beds and planters are positioned around the entrance, adding natural beauty to the landscape.
Home in Oshkosh
4.87 out of 5 average rating, 128 reviews

Cozy getaway 1 mile from downtown and UWO campus!

2 bedroom home with a living room and dining room, kitchen with appliances, laundry room and Big backyard. (Kid friendly) Grocery store, gas station, and restaurants are less than a mile away. (Within walking distance) Great, clean neighborhood. Only a mile from Menominee park, arena, and other destinations you may want to explore.

Popular amenities for Oshkosh holiday rentals

Quick stats about holiday rentals in Oshkosh

  • Total rentals

    840 properties

  • Nightly prices starting at

    ₹879 before taxes and fees

  • Total number of reviews

    8.5K reviews

  • Family-friendly rentals

    670 properties are a good fit for families

  • Pet-friendly rentals

    230 properties allow pets

  • Rentals with a pool

    40 properties have a pool

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Winnebago County
  5. Oshkosh