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
Home in Omro
5 out of 5 average rating, 15 reviews

Fox River Fishing & Relaxation

Newly remodeled home on the Fox River. Perfect for a fishing trip, family getaway or time with your friends! This property comes with all the amenities you will need from a fish cleaning station to high speed WIFI, Spectrum TV & beds that were picked out with the utmost comfort in mind! Bring your boat and tie up to the seawall so you can jump in to fish on the Fox River and various lakes. The outdoor space is ideal for relaxation, meals, games and time by the firepit. Enjoy beautiful sunsets!

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, 70 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.

Top guest favourite
Home in Oshkosh
4.99 out of 5 average rating, 142 reviews

LakeHome! Relaxing! Cozy! Amazing Sunsets!

On the shore of Lake Butte Des Morts Longer stays welcome!!! Awesome Lake view private pier for fishing/relaxing(we do not allow anything to be tied up to pier at any time) Beautiful Sunsets Gas fireplace Shopping/restaurants/etc Near EAA Approx. 40 miles from Lambeau Field fire pit grill Lake view Bedroom,Living Room,Dining area Near by Wiouwash trail for hiking, biking, etc.. Kitchen space for cooking. Washer/dryer Larger 1 bedroom /Queen Sleep Number mattress Off street parking

Top guest favourite
Home in Oshkosh
4.94 out of 5 average rating, 115 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
A cozy firepit area is surrounded by eight Adirondack chairs, set against a backdrop of a vibrant sunset over the lake. The scene is framed by smooth pebbles, while a 60-foot dock extends into the water, creating a serene outdoor atmosphere.
Home in Menasha
4.94 out of 5 average rating, 251 reviews

Designer Lakefront Home with Views, Firepit, Dock

Relax at Sunset Oasis, where stunning lake views and sunsets set the tone for your stay. Sip coffee in the chef’s kitchen, paddle out in kayaks, grill lunch, and dine lakeside. In the evening, cozy up by the fireplace or gather around the firepit under the stars. Stream your favorite shows on the smart TV or explore nearby downtowns just minutes away. This stylish, updated luxury lake house is the perfect escape to unwind, reconnect, and create unforgettable memories.

Top guest favourite
The cottage features a long, metal-roofed exterior with gray siding and contrasting purple shutters. Lush greenery surrounds the home, including decorative flower beds. A paved pathway leads to the entrance, highlighting the spacious yard. Sunlight enhances the bright and welcoming appearance.
Guest house in Oshkosh
4.95 out of 5 average rating, 195 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, 69 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 rustic red cabin is framed by lush green reeds along the edge of a tranquil body of water. The clear blue sky reflects on the gentle ripples of the lake, while patches of green algae are visible in the water, enhancing the natural setting.
Farm stay in Omro
4.99 out of 5 average rating, 90 reviews

Private Island Cabin + 170 Scenic Acres to Explore

Abundant wildlife, calming lake views, and quiet, starry nights. Accessible only by boat, this beautiful but bare-bones cabin is for the real adventurers. The main property (which includes 160 acres of protected wildlife habitat) is a short paddle away, giving the perfect balance of convenience and seclusion. Although rough around the edges, the cabin's natural privacy and minimalist style are perfect for anyone who enjoys the outdoors.

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, 323 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!

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
4.92 out of 5 average rating, 309 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
A screened-in porch features a dining table surrounded by comfortable seating. Large windows provide unobstructed views of the landscaped lawn and lake, with trees and a dock visible through the screens. A rocking chair adds a cozy touch to the inviting outdoor space.
Home in Oshkosh
4.93 out of 5 average rating, 15 reviews

Lakefront 4br W/ Dock & Kayaks | Oshkosh

Whether you are visiting for EAA AirVenture, a summer family reunion, a corporate retreat, or simply a weekend escape on the water, Sunset Cove delivers a rare combination of modern design, outdoor recreation, and lakefront serenity that is hard to find in this market. Welcome to Sunset Cove, a brand-new lakefront retreat on the shores of Lake Butte des Morts in Oshkosh, Wisconsin.

Guest favourite
Home in Oshkosh
4.89 out of 5 average rating, 9 reviews

Luxury Solar Envelope Home w/ indoor Sauna

Spacious solar envelope home designed for comfort and connection, sleeps up to 10 guests. Indoor Sauna, fully equipped kitchen, 3-seasons porch, 65" TV, and open living areas invite gathering and relaxation. Outdoors, enjoy the Crystal propane coffee table, fire pit and BBQ grill - with plenty of seating - perfect for families or groups year-round. 6.3 miles from EAA fairgrounds!

Popular amenities for Winnebago County holiday rentals