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
Cabin in Elkhart Lake
4.99 out of 5 average rating, 317 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
A modern living area features a striking brick fireplace as a focal point. Natural light floods in through large windows, illuminating the hardwood floor. A comfortable gray couch is positioned beside a black chair, with a TV visible across the room.
Home in Appleton
5 out of 5 average rating, 139 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.

Guest favourite
A historic lighthouse stands at the water's edge, illuminated by the vibrant colors of sunset. Smooth stones line the shoreline, reflecting the serene lake. Lush greenery is visible in the background, creating a peaceful coastal setting.
Home in Fond du Lac
4.92 out of 5 average rating, 99 reviews

Woltring Waters Waterfront Home

Wake up to a beautiful view of Lake Winnebago, and enjoy you cup of coffee with the sound of crashing waves off the back porch. You will have breathtaking sunsets with the historical light house backdrop that is in viewing distance from the property. From dining to convenient stores everything you need is in walking distance. Take a peaceful stroll around the marina or take the kids to Lakeside Park, offering a petting zoo, carousel, train, jungle gym & splash pad. Everyone will enjoy!

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, 201 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, 108 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, 192 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 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, 103 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
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, 238 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
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
4.97 out of 5 average rating, 311 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.

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, 239 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.

Superhost
Home in Oshkosh
4.85 out of 5 average rating, 273 reviews

Cozy Retreat • Fireplace Loft •Walk to Park & Lake

🍁 Cozy 3BR family retreat across from Menominee Park & Lake Winnebago! Enjoy fall walks to the beach, zoo, and trails—all just steps away. Minutes from downtown Oshkosh, including dining and shops. Features a new upstairs lounge with large TV and fireplace, king suite, and basement bar—perfect for family time and Thanksgiving gatherings. Includes driveway parking and easy self check-in for a smooth 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, 297 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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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 townhouse rentals in Oshkosh?

    Oshkosh has more than 10 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cottage rentals in Oshkosh?

    Experience the best of Oshkosh with our cottage rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do condo rentals in Oshkosh have wifi?

    Absolutely! We offer over 10 condo 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 house rentals in Oshkosh have air conditioning?

    Absolutely! We offer over 670 house rentals with air conditioning in Oshkosh. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 70 homes with wifi, over 70 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 € 9 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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