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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 suite in Winneconne

4.81 out of 5 average rating, 212 reviews

Lake Winneconne Area Cottage

Northwoods-ish rustic cabin: 750 sq.ft., open-concept, lotsa windows, repurposed oak floor, 3/4 bth, equipped kitchen, dining/fun bar, two decks, E &W. 1 Qn, 1 dbl bed, qn. hide-a-bed, 1 twin. Optional: qn or twin air-bed. Desk, dresser, views , cable TV, wifi, stereo, heat/AC. Access to Lake Winneconne public boat ramp, 200 yrds! On-site & off-st. parking trailers. Quiet neighborhood; 3 mi. from Winneconne; easy access to Oshkosh, Green Bay, Fox Cities. Fun, not fussy seasonal decor.

Guest favourite

Loft in Amherst

4.95 out of 5 average rating, 102 reviews

Tiny Town Bakery Flatlet

Ever wanted to see what goes on in a commercial bakery? Imagine waking to the aroma of baking bread and cinnamon rolls? Get a bird's eye view into the kitchen of the Village Hive Bakery Kitchen while staying in the newly renovated "flatlet". Salvaged & repurposed building supplies used to create a unique studio apartment above the bakery retail. Guests can enjoy the retail farmhouse table and comfortable seating space by the Main Street picture window. Cooking/baking classes available.

Guest favourite

Home in Oshkosh

4.88 out of 5 average rating, 169 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, 244 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, 157 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, 108 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

Cabin in Wild Rose

4.9 out of 5 average rating, 510 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

4.95 out of 5 average rating, 184 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, 202 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

Rental unit in Neenah

4.84 out of 5 average rating, 111 reviews

Cozy and Simple Downtown Space

Enjoy this great space in a quiet safe neighborhood. The space has a comfortable bed, 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.

Guest favourite

Home in Oshkosh

4.96 out of 5 average rating, 182 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

4.91 out of 5 average rating, 248 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!

Holiday rentals for every style

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Flats

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Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Oshkosh holiday rentals

Free parking on premises

Air conditioning

Stay near Oshkosh's top sights

EAA Aviation Museum89 locals recommend

Paine Art Center and Gardens54 locals recommend

Fox River Brewing Company Waterfront Restaurant43 locals recommend

Menominee Park Zoo38 locals recommend

Becket's35 locals recommend

Outlet Mall station29 locals recommend

Other great holiday rentals in Oshkosh

Guest favourite

Guest suite in Fremont

4.98 out of 5 average rating, 80 reviews

Mother in law suite without the mother in law

Guest favourite

Home in Appleton

4.96 out of 5 average rating, 23 reviews

Cozy Two Bedroom Home

Guest favourite

Home in Oshkosh

4.83 out of 5 average rating, 84 reviews

Jackson Farmhouse

Guest favourite

Home in Fond du Lac

4.87 out of 5 average rating, 67 reviews

Country home with fireplace, sauna & putting green

Guest favourite

Home in Oshkosh

5 out of 5 average rating, 15 reviews

3 min Downtown*6 to UWO *Desk*Park*Full kitchen*WD

Guest favourite

Home in Fond du Lac

4.89 out of 5 average rating, 47 reviews

Woltring Waters Waterfront Home

Guest favourite

Home in Oshkosh

5 out of 5 average rating, 31 reviews

Our Little Lake House

Guest favourite

Rental unit in Neenah

4.75 out of 5 average rating, 8 reviews

Unit 19 at Fox Flats (1 Bed/Garage/Washer & Dryer)

Quick stats about holiday rentals in Oshkosh

Total rentals
830 properties
Nightly prices starting at
₹840 before taxes and fees
Total number of reviews
6.2T reviews
Family-friendly rentals
650 properties are a good fit for families
Pet-friendly rentals
220 properties allow pets
Rentals with a pool
40 properties have a pool

Destinations to explore