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

Rental unit in Appleton

4.97 out of 5 average rating, 129 reviews

Homey lower level apartment with private entrance

This living space is in the lower level of our ranch home, which is located in a lovely and quiet neighborhood. The furnishings in this area are mostly antique pieces that came from special family members. You may also use the screen porch and patio for relaxing. You will have a private entrance through the garage so you can come and go as you like. The kitchen is furnished so you may cook; there is no dishwasher. We will furnish paper products. There are also many restaurants close by.

Guest favourite

Home in Oshkosh

4.87 out of 5 average rating, 158 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!

Guest favourite

Cottage in Fond du Lac

4.97 out of 5 average rating, 238 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 queen bed and 2 twin beds, 1 full bathroom, and a fully stocked newly remodeled kitchen. Perfect getaway for some R&R with family or friends.

Guest favourite

Cabin in Fox Lake

4.96 out of 5 average rating, 142 reviews

Cabin on the Trail

Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing, swimming and boating and in the winter have fun ice fishing by walking to the lake out your back door! *Please read the full description and look at all of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum, including children. *All dogs/pets must be pre-approved by the host. There is a $50 fee/stay.

Guest favourite

Home in Oshkosh

4.99 out of 5 average rating, 100 reviews

Beautiful Warm and Cozy Lake Home Sunsets and more

Beautiful cozy and comfortable home located in a small neighborhood on the east shore of Lake Butte Des Morts .Spacious One bedroom with sleep number queen bed and view of the lake. Spacious living room with gas fire place overlooking the lake. Kitchen, one bathroom and laundry room. Spectacular sunsets, fishing, perfect place to enjoy a camp fire! Short walk to Wiouwash Trail for biking, walking and snowmobiling. Close to EAA Grounds, Oshkosh Outlet Mall and great restaurants.

Guest favourite

Home in Wautoma

4.88 out of 5 average rating, 103 reviews

Lakefront Home on quiet sandy lake! All seasons

Beautiful lakeside home with wall of windows facing the lake. Giant 2-acre lot feels like you're entering the wilderness, with huge lake frontage. 40-foot deck overlooking Lake Alpine, a sand-bottom lake full of fish. Swim next to the dock (shallow). Gentle sloping path to lake- no steps. Gas fireplace to stay cozy on cool nights. Your own dock, pedalboat, canoe, kayaks, toys and forest to explore. Summer fun and 5 min. to skiing, tubing, snowshoeing, snowmobiling.

Guest favourite

Cabin in Wild Rose

4.9 out of 5 average rating, 420 reviews

Getaway Wild Rose - Milwaukee

An easy drive from the city, Getaway is a new way to experience the great outdoors. Nestled across dozens of acres of private woodlands, our modern, tiny cabins have everything you need (comfy bed, bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you relax, unwind and disconnect from the everyday. Plus, as part of your stay, you'll receive firewood, a s'mores kit, coffee and bottled water*.

Guest favourite

Guest house in Oshkosh

4.96 out of 5 average rating, 178 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.

Guest favourite

Home in Oshkosh

4.91 out of 5 average rating, 192 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

Home in Oshkosh

4.96 out of 5 average rating, 176 reviews

Character Home by Lake Winnebago

Charming 1930s home, 1 block from Lake Winnebago. Quiet neighborhood. Completely renovated with all the amenities you could want. Within walking distance of Menominee Park and a short drive or bike ride to downtown Oshkosh. Enjoy the farmers market on Saturday's June-October. Several music festivals throughout the year. Fishing tournaments and activities year around. Perfect for ice fishing. Bring your shanty! There’s lake access a block away.

Guest favourite

Rental unit in Oshkosh

4.84 out of 5 average rating, 158 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

Cabin in Hancock

4.98 out of 5 average rating, 188 reviews

Peaceful Cabin in the Woods

Our cabin has all the amenities a family could need, but is the perfect getaway from city life. Located on 5 secluded acres in Hancock, Wisconsin. Minutes from downtown Wautoma. Surrounded by woods on all sides, with plenty of open area for outdoor activities. A peaceful setting to enjoy a cup of coffee or a glass of wine while listening to the birds from the porch swing, or around the crackling fire at night, toasting marshmallows.