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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Guest favourite
A bright sunroom features large windows offering views of the lake. Two chairs and a small table are arranged on a patterned rug, inviting relaxation. Natural light fills the space, highlighting the serene atmosphere and the vibrant colors of the surrounding nature.
Home in Oshkosh
4.84 out of 5 average rating, 135 reviews

Linger Longer On The Water

Cozy lake cottage on the west shore of Lake Winnebago featuring 3 bedrooms and 1 bath. Beautiful sunrises over the lake and just minutes from everything in Oshkosh Wisconsin. Large kitchen for preparing meals or just hanging out. 5 minute walk to Menominee Park. 6.5 miles to EAA Grounds. Less than 10 minutes to downtown and the University of Wisconsin, Oshkosh campus, shopping, restaurants and Main Street. Great location for walking, bike riding and just seeing the local sites. Park on site.

Top guest favourite
The exterior of the barn features a sleek black facade with white trim, including multiple windows that allow natural light to enter. A wooden fence provides privacy, and the entrance is marked by a simple white door. Lush greenery surrounds the barn, enhancing its rustic charm.
Cabin in Princeton
4.99 out of 5 average rating, 117 reviews

Private Riverfront, Converted Barn *EV Charger*

Fox River Barn is located in a picturesque setting with stunning views of the Fox River in Princeton, WI. This 1940s barn has been lovingly converted into a comfortable living space with modern features and amenities, making it the perfect retreat for a romantic getaway or a peaceful escape from the city. Inside, the bones of the barn are present. From beams and rafters on the main level to the tall, gable barn ceiling. Just imagine all the different ways the barn had been used over time.

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, 104 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.

Guest favourite
A well-lit hallway features smooth wooden flooring and white walls. Two framed botanical prints are displayed on the left. A small table with a plant is positioned near the doorway, which opens into a bathroom. Light filters in from the bathroom window.
Flat in Downtown Neenah
4.85 out of 5 average rating, 187 reviews

Cozy and Simple Downtown Space

Enjoy this great space in a quiet safe neighborhood. One car allowed at the property! The space has comfortable beds, provided hygiene products, a smart TV and snacks + beverages. Wake up and enjoy coffee provided by us. Shops and restaurants within walking distance! Visit The Plaza downtown with ice skating, fire pits, a coffee shop and more. Great for a couples getaway. Luxury for a great price! A portion of the proceeds from bookings go to housing evacuees, refugees and veterans.

Top guest favourite
A remodeled kitchen and living area feature neutral tones and modern appliances. Bar stools are positioned at a counter, while a washer and dryer are present nearby. A dark brown armchair and a square ottoman are set on the soft carpet beside a small coffee table.
Cottage in Fond du Lac
4.98 out of 5 average rating, 299 reviews

Cozy Guest House with Lake views.

Our remodeled two bedroom Guest House is adjacent to our Cottage and offers beautiful lake views. Access to Lake Winnebago available at near by boat launches. 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 king and queen beds, 1 full bathroom, and a fully stocked newly remodeled kitchen. Perfect getaway for some R&R with family or friends.

Top guest favourite
A spacious living area features a dark leather sectional and a wooden coffee table. A sleek electric fireplace is mounted on a rustic wooden wall, complemented by a large flat-screen TV. Natural light filters through the windows, illuminating the open kitchen and dining area beyond.
Home in Oshkosh
4.94 out of 5 average rating, 102 reviews

Leonard Point Birdhouse

Welcome to the Leonards Point Bird House! This newly renovated lake home has all amenities needed for a perfect escape in Oshkosh, WI. You will experience lake views from the south side of Lake Butte Des Morts. For a quieter experience (or louder for the kids) there is a detached bunk house with its own bathroom! The Birdhouse is 10 minutes away from highway 41 and multiple stores for easy access to everything you need. Please feel free to reach out with any questions!

Top guest favourite
Home in Oshkosh
4.99 out of 5 average rating, 135 reviews

Cozy Relaxing Lake Home with spectacular sunsets!

On the shore of Lake Butte Des Morts Longer stays welcome!!! Beautiful Sunsets Shopping/restaurants/etc… Approx. 40 miles from Lambeau Field pier/summer,sorry nothing can be tied up to pier at any time solo fire pit grill Lake view Bedroom,Living Room,Dining area Near by Wiouwash trail for hiking, biking, etc.. Near EAA Gas fireplace Living / dining area Kitchen space for cooking. Washer/dryer Larger 1 bedroom /Queen Sleep Number mattress Off street parking

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, 236 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 welcoming two-story home features a light gray exterior with white trim. A front porch, adorned with potted flowers, provides seating options. A landscaped yard with green grass and mulch surrounds the home, enhancing the inviting curb appeal.
Home in Appleton
4.89 out of 5 average rating, 321 reviews

The Tree House. Whole house. Enjoy Appleton!!!!

Cozy downtown Appleton home close to everything Appleton has to offer!! Within walking distance to Farmers Market, Fox Performing Arts Center, restaurants and within 30 minute drive to world famous Lambeau Field home of the Green Bay Packers!! Enjoy the tranquil backyard with one of the biggest maple trees in the city, enjoy vintage artwork and spin classic vinyl in the music room. Fall 2025 just around the corner. The house is yours! No other guests.

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, 235 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
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, 296 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!

Guest favourite
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, 130 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

When is the best time to visit Oshkosh?

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Avg. price£138£139£128£203£152£155£366£189£151£146£149£138
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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Oshkosh?

    Yes! Work meets play with ease at over 340 vacation rentals in Oshkosh featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Oshkosh?

    Four-legged friends are welcome in Oshkosh. Choose from more than 230 vacation rentals for guests traveling with pets.

  • Are there Oshkosh vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Oshkosh, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly apartment rentals in Oshkosh?

    Oshkosh has more than 40 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in bed and breakfast rentals in Oshkosh?

    Experience the best of Oshkosh with our bed and breakfast rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Oshkosh have wifi?

    Absolutely! We offer over 70 apartment rentals with wifi in Oshkosh. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oshkosh have a bbq area?

    Absolutely! We offer over 210 house rentals with a bbq area in Oshkosh. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Oshkosh have a gym?

    Absolutely! We offer over 110 house rentals with a gym in Oshkosh. Enjoy a tailored experience with all the comforts you desire.

  • Do townhouse rentals in Oshkosh have air conditioning?

    Absolutely! We offer over 10 townhouse rentals with air conditioning in Oshkosh. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Condo Rentals in Oshkosh?

    Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Oshkosh

  • Total holiday rentals

    Explore 840 holiday rentals in Oshkosh

  • Nightly prices starting at

    Oshkosh holiday rentals start at £8 per night before taxes and fees

  • Verified guest reviews

    Over 8,530 verified reviews to help you choose

  • Family-friendly holiday rentals

    670 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 230 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    340 properties have a dedicated workspace

  • Wifi availability

    820 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!

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