Holiday rentals in Winnebago County

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Top-rated holiday rentals in Winnebago County

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Superhost

Guest suite in Winneconne

4.81 out of 5 average rating, 227 reviews

Lake Winneconne Area Cottage "CabinSong" tradition

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.

Top guest favourite

Home in Oshkosh

5 out of 5 average rating, 38 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.

Guest favourite

Home in Oshkosh

4.83 out of 5 average rating, 100 reviews

Jackson Farmhouse

PERFECT FOR ANY FAMILY, CONFERENCE / EVENT ATTENDEE AND YOUR GROUP! Our beautifully restored 100 YEARD OLD farm house is located on Jackson St in Oshkosh giving you quick and easy access to highway 41! **Please note this home is old and has sloping floors and a few drafts** The easy in and out driveway can hold at lease 8 cars if needed during your stay at our comfortable property. After a long day of whatever you may be in town for you'll be able to relax in your own piece of country!

Guest favourite

Home in Oshkosh

4.88 out of 5 average rating, 187 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

Flat in Neenah

4.86 out of 5 average rating, 157 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

Home in Oshkosh

5 out of 5 average rating, 16 reviews

Cozy 2 Bedroom Home in Oshkosh

We are located about 10 minute drive from EAA AirVenture. We are only 1 mile from the Downtown Oshkosh, which hosts a great farmers' market on Saturdays and many small businesses. There are various grocery stores and restaurants within walking distance of our house. Prepare delicious meals in our fully equipped kitchen. Bedrooms are furnished with comfortable beds, and soft linens. The bathrooms are clean and stocked with fresh towels and toiletries. Family and pet friendly.

Top guest favourite

Guest house in Oshkosh

4.95 out of 5 average rating, 189 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

Flat in Winneconne

4.98 out of 5 average rating, 51 reviews

Boathouse Bungalow

The Boathouse Bungalow is the uniquely perfect getaway located on the river in Winneconne, WI. This bright one bedroom apartment is located on the backside of a large and historical boathouse just a few blocks from the downtown area and features a permanent dock for use. Located in a no-wake zone, the dock is perfect for fishing or tying up a boat overnight. Also close to walking and snowmobile paths, the Boathouse Bungalow is the ultimate retreat for exploring!

Top guest favourite

Home in Oshkosh

4.92 out of 5 average rating, 216 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

Farm stay in Omro

4.9 out of 5 average rating, 79 reviews

Comfy Cabin on 170 Beautiful Acres - Come Explore!

The cabin rests on 180 acres of scenic farm wildlife habitat. The property includes an 1800s-era barn & blacksmith shop, a host of wild & domestic animals, miles of private canal with access to the Wolf & Fox Rivers, a hiking trail, garden, orchard, and much more! The farm has been the pride of our family for 6 generations. A converted grainary, the cabin features a queen bed, full kitchen, full bathroom, high-speed satellite Wifi and smart-TV.

Guest favourite

Home in Oshkosh

4.87 out of 5 average rating, 238 reviews

3BR Across from Park • Watch Fireworks from Porch!

Unbeatable Fourth of July Location! 🎆 Watch Menominee Park’s spectacular fireworks burst directly overhead from the front yard or porch — one of the best views in Oshkosh, just steps from the park! This cozy, modern getaway is perfect for families, groups, or peaceful retreats. Enjoy a stylish interior, gazebo with firepit table, and unbeatable access to the lake, zoo, walking trails, and downtown Oshkosh — all just a short stroll away.

Guest favourite

Flat in Oshkosh

4.86 out of 5 average rating, 214 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.

Holiday rentals for every style

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Popular amenities for Winnebago County holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Winnebago County

Guest favourite

Home in Oshkosh

5 out of 5 average rating, 13 reviews

3+ bd 3 bath in Oshkosh on River near EAA

MikiRating, 5 stars2 weeks ago

I was in town for my dad’s memorial and Shawn worked with me to ensure that I was able to focus on my family during that time. We needed a peaceful location where I could bring my mom and her houseguests for meals and relaxation while we prepared her house for the gathering. Shawn’s house was perfect with plenty of indoor and outdoor seating, including a lovely fire pit with wood for evening fires. The deck was a lovely place for morning coffee. A bonus for the kids were all the “hidey holes” throughout the that made the house seem almost magical. Watching the lift bridge go up and down, the bank anglers, princess parties at the lovely park across the canal all added to the charm while still feeling very private. Highly recommend!

Top guest favourite

Home in Oshkosh

5 out of 5 average rating, 27 reviews

Menominee House Lake View

MichelleRating, 5 stars1 month ago

Nate was super easy to work with. We only stayed one night so we probably didn’t get to enjoy the house to the fullest but the game room was fun for the younger guests while we were there and the beds were comfortable.

Guest favourite

Cottage in Neenah

4.94 out of 5 average rating, 479 reviews

Lake Life, year round hot tub!

HeatherRating, 5 stars2 weeks ago

We stayed for three nights and enjoyed our selves very much! Pros about staying: Full Kitchen - I had everything I needed to cook and serve. Seasoning and sauces available too Coffee Bar - Had a cute coffee area with flavors, teas, coffee, big comfy cups and more Hot Tub - Clean, comfy, private.. loved it! Lake View - Beautiful Views, easy access to the lake. gorgeous sunrises and sunsets that you can look at through the large windows or the patio. Clean - Very Clean home! Bedrooms - Large bedrooms with closet space to put your clothing in. Ceiling fans in each room. Cot and a pack and play available. Comfy soft beds with plenty of pillows and blankets Dining - table for 8 and a kitchen island that seats 6 Entertainment - Plenty of board games Communication - he sent us "how to" videos on how to use the fire pit and hot tub - genius if you ask me! Appliances - Great, clean washer and dryer and Dish washer. Air Conditioner was easy to use and access. Shower - water pressure was great!

Top guest favourite

Home in Oshkosh

4.98 out of 5 average rating, 64 reviews

Hickory on the LakeWaterfront Luxury on Winnebago

RickyRating, 5 stars2 weeks ago

The stay was quite peaceful and a nice escape. The place was quite clean and well maintained. I would recommend the house for you next getaway

Flat in Oshkosh

5 out of 5 average rating, 3 reviews

Newly Renovated Upper Unit

SaraRating, 5 stars1 week ago

Beautifully renovated, very clean and cozy. I'm picky about bedding, and the comfortors were amazing. Private and easy entry to the upper floor. Nice touches like a wall cornhole game and really cool full length mirrors. It was the perfect spot for our needs, and we will book again next time we are in Oshkosh!

Flat in Oshkosh

4.86 out of 5 average rating, 206 reviews

Quaint 2 bedroom upper apartment in duplex.

Er-JinRating, 5 stars1 month ago

A friend and I stayed here for about a week to attend an event in town. Steve, our host, was super flexible with our arrival time and very accommodating. He even went out of his way to supply us with an iron and board last minute, and we really appreciated that! Thank you Steve for having us!

Superhost