Holiday rentals in Winnebago County

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Top-rated holiday rentals in Winnebago County

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 74 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.

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Home in Oshkosh
5 out of 5 average rating, 5 reviews

The Goldfinch | Centrally Located Oshkosh Gem

Welcome to The Goldfinch — a warm, thoughtfully designed home blending classic character with modern comfort in a quiet Oshkosh neighborhood walking distance from restaurants and recreational trails including the river walk and Wiouwash Trail. Our home features comfortable bedrooms, a fully equipped kitchen, fast Wi-Fi, a private hot tub, and even a movie theatre. Whether you're visiting for family, work, or a weekend away, you'll find a comfortable place to relax, recharge, and feel at home.

Top guest favourite
The bedroom features a spacious bed covered with a multicolored quilt. A wooden dresser and a vintage mirror are positioned nearby, with warm lighting creating a cozy atmosphere. Soft colors adorn the walls, complementing the overall calming effect of the room.
Home in Winneconne
5 out of 5 average rating, 23 reviews

Near lakes and restuarants

Welcome to our lovely 2 bed, 1 bath "cottage" in Winneconne! This charming home combines comfort and convenience in a safe and vibrant community. Relax and enjoy restful nights at our home, and prepare meals in the fully equipped kitchen. The bathroom is stocked with fresh towels and other essentials. Located near boat landings, you'll have easy access to the river and lakes. You'll love the walkable neighborhood, just blocks from restaurants and bars. Book now and enjoy a relaxing getaway!

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, 213 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
Home in Oshkosh
4.94 out of 5 average rating, 118 reviews

Leonard's 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, 146 reviews

Relaxing Lakefront Getaway on Lake Butte des Morts

Relax at our spacious lakefront retreat on Lake Butte des Morts in a small and friendly neighborhood! Enjoy stunning sunsets, beautiful lake views from the bedroom, living room, and dining area, plus a private pier for fishing and relaxing. Features include a queen Sleep Number bed, gas fireplace, full kitchen, washer/dryer, fire pit, grill, and off-street parking. Near EAA, restaurants, shopping, the Wiouwash Trail, and just 40 miles from Lambeau Field. Longer stays welcome!

Top guest favourite
Guest house in Oshkosh
4.96 out of 5 average rating, 200 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.

Top guest favourite
A modern living room features a comfortable gray sofa adorned with patterned cushions. A large area rug with a chevron design anchors the space. A wall clock and artwork complement the decor, with a glimpse of the kitchen area visible in the background.
Flat in Winneconne
4.99 out of 5 average rating, 70 reviews

Boathouse Bungalow

Enjoy a unique getaway in our historic “Boathouse Bungalow” on the Wolf River. The location could not be more perfect when visiting the scenic Fox River Valley; close to walking paths, snowmobile trails and within walking distance to downtown Winneconne. The permanent dock is in a no-wake zone, great for fishing, tying up boats or just relaxing. Located 12 miles to Oshkosh, 23 to Appleton and 48 to Lambeau. A wonderful retreat for making lasting memories.

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, 249 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 modern dining area features a large, marbled table surrounded by sleek black chairs. The open kitchen is visible in the background, showcasing dark cabinetry and stainless steel appliances. Natural light brightens the space, enhancing the clean lines and neutral color palette.
Home in Menasha
4.98 out of 5 average rating, 103 reviews

Perfectly Located Cozy 2 Bedroom

*Home away from home, Grocery Store and Gas Station just around the corner, for all of your basic needs. *Enjoy a stylish experience at this centrally-located place. *Quick, Easy access to highway 441 to get you where you need to be. *Green Bay (Packer Games, Resch Center, Titletown District, Epic Event Center) 25 minutes *Fox River Mall 10 minutes *Downtown Appleton 5 minutes (PAC, Mile of Music, Octoberfest) *Oshkosh 20 minutes (EAA, Outlet Mall)

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, 265 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
An open living space features warm wooden beams and a mix of modern and rustic decor. A comfortable sofa and armchair are arranged around a coffee table, while a dining area accommodates six. Natural light enters through large windows, complemented by a vintage map on the wall.
Cabin in Winneconne
4.97 out of 5 average rating, 326 reviews

Barndominium: Goats, Hot Tub, Forest & River

The Cloverland Barndominium is a thoughtfully renovated 100-year-old barn sitting on 5+ private acres of forest to explore next to a river. You'll share the land with friendly goats that you can watch from right outside your window! Outside you'll enjoy walking the trails, feeding the animals, taking the canoe down the river, making a fire in the fire pit, and exploring the forest. Escape the busy world and reset!

Popular amenities for Winnebago County holiday rentals