Holiday houses in Waupun

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Top-rated holiday rentals in Waupun

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Guest favourite

Cabin in Hancock

4.95 out of 5 average rating, 383 reviews

Peaceful Wooded Sanctuary- with private dog park!

Unplug. Unwind. Connect with nature. Come enjoy our 700 sq.ft. cabin on 6 wooded acres. Fish the trout stream, hike, bike, swim! See hummingbirds hover at the feeder, watch for deer or bald eagles. The outdoor recreational opportunities are endless. Listen to the wind whisper while you sway in the hammock. Play in the treehouse! Escape to the peaceful pines and let whippoorwills sing you to sleep at day's end. The cabin accommodates every guest, dogs too! New in 2023, a 1,200 sq. ft. dog park.

19–26 Sep

$299 NZD per night

Guest favourite

Cottage in Fond du Lac

4.97 out of 5 average rating, 234 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.

22–29 Sep

$124 NZD per night

Guest favourite

Cabin in Fox Lake

4.95 out of 5 average rating, 122 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.

2–9 Mar

$198 NZD per night

Guest favourite

Bungalow in Green Lake

4.83 out of 5 average rating, 145 reviews

Peaceful Bungalow in Green Lake

Bright and airy bungalow located within short walking distance to downtown Green Lake, restaurants, boutiques, and boat rentals when in season. Located on beautiful Lake St, one block off the lake and with a partial lake view. The bungalow comes with 3 bedrooms, 1 bath, fully equipped galley kitchen, Cable TV, and WIFI. The huge screened-in porch is perfect for morning coffee and evening cocktails spring, summer and fall. Large sunny backyard. Come relax in beautiful Green Lake!

5–12 Jan

$260 NZD per night

Guest favourite

Home in Campbellsport

4.99 out of 5 average rating, 136 reviews

Gleason's Chouse

You'll love staying in our unique home, in a quiet neighborhood. This is a recently remodeled 1867 church converted to a "Chouse". Featuring 2 bedrooms, Full Kitchen, 1 Bathroom, Balcony, Parking, and a Gazebo.. all beautifully complimented by a range of antiques and decorations. 8 Miles East of Hwy 41, a 45 min drive to Oshkosh or an hour to Milwaukee. Just down the from Lake Bernice & Eisenbahn Bike Trail. Also close enough to the Kettle Moraine Forest to hike and sightsee!

11–18 Aug

$229 NZD per night

Guest favourite

Home in Fond du Lac

4.91 out of 5 average rating, 53 reviews

Country home with fireplace, sauna & putting green

Country three bedroom home in close proximity to Oshkosh, Fond du Lac, and Appleton. Lake Winnebago is only two miles away with room in the driveway to park a boat. Comes with many amenities including an indoor gas fireplace, large patio, garden pond, sauna, outdoor shower, table tennis, and putting green. The houses interior has been completely remodeled and has an inviting outdoor space with mature trees and unique features. Ideal for a wide variety of interests and uses.

24 Sep – 1 Oct

$293 NZD per night

Guest favourite

Cabin in Wild Rose

4.92 out of 5 average rating, 312 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*.

22–29 Sep

$243 NZD per night

Guest favourite

Cabin in Coloma

4.95 out of 5 average rating, 109 reviews

Hunter's Drift - a cozy cabin in the woods

Our quaint log cabin overlooks a small pond and is situated on 40 acres of woodland; the only other development on the property is a charming farmhouse down the lane (our home). Cozy up with a good book next to the wood-burning stove. Watch the local wildlife from a rocking chair on the covered porch. Gaze at the stars on a clear night. Visit nearby trout streams, antique stores, and local sights, then come back to this simple, well-appointed respite in the woods.

8–15 Jul

$286 NZD per night

Guest favourite

Cottage in Fox Lake

4.85 out of 5 average rating, 285 reviews

The Little White Cabin, Fox Lake WI

****As of October 15, 2023, all of the piers are out of the water for the winter season.**** This 2 bedroom rustic cottage feels like you're home at the beach. Light colors, easy comfort. Everything you would expect for a summer cottage, boat launch is close, great fishing, water skiing, jet skiing. Winters are for ice fishing and snow mobiles. Cozy comfort. If you are a hunter, this is your cabin for longer term rentals during fall/winter. LGBTQ friendly!

18–25 Jan

$245 NZD per night

Guest favourite

Cottage in Beaver Dam

4.95 out of 5 average rating, 19 reviews

Cozy lakeside getaway

Relax at this peaceful lakeside cottage. Launch your canoe or kayak at the private dock (May to Sept) or your power boat at the nearby county park, prepare food in the kitchen, lounge on the three-season porch, and build a fire in the evening. This 1950s fishing cottage has been updated with modern amenities. Only an hour from Madison or Milwaukee, you'll feel stress fall away in the gentle lake atmosphere. Treat yourself to a few days at Stillwater Cottage!

27 Nov – 4 Dec

$318 NZD per night

Guest favourite

Farm stay in US

4.98 out of 5 average rating, 181 reviews

Family friendly farmstay just outside Milwaukee

The Inn at Paradise Farm is an original 1847 log homestead in rural Wisconsin just a short drive from Milwaukee and close to many attractions, especially for nature lovers. Our very spacious private 4-room suite with private entrance is comfortable for couples, families, or business travelers who long to unwind in a pastoral setting. Visit with, and even help care for, our friendly animals! We are licensed and inspected. Paradise Farm welcomes all.

6–13 Jan

$205 NZD per night

Guest favourite

Apartment in Oshkosh

4.86 out of 5 average rating, 142 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.

26 Sep – 3 Oct

$161 NZD per night