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Vacation rentals in Waupun

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Top-rated vacation rentals in Waupun

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Home in Juneau

4.82 out of 5 average rating, 111 reviews

Take a Break at Lakeside Acres

Lakeside Acres; a 2-bedroom, 1 bath vacation rental home located on beautiful Lake Sinissippi. Open concept living area with furnished patio and private dock. This newly updated home provides the perfect summer getaway or winter retreat for family and friends. Whether you spend your days kayaking with the complimentary kayaks, exploring Horicon Marsh, or soaking up the sun on the dock, you're sure to have an unforgettable stay in this lakefront hideaway. Note: Docks are not in the lake Nov-Apr

Feb 16 – 23

G$36,592 GYD per night

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.

Sep 19 – 26

G$33,124 GYD per night

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.

Sep 14 – 21

G$13,973 GYD per night

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.

Dec 3 – 10

G$22,404 GYD per night

Apartment in Ripon

4.95 out of 5 average rating, 21 reviews

Downtown Loft with historic charm

Stay in historic downtown Ripon, less than a block away from it all! It has large beautiful windows to watch the downtown bustle, as well as see the magical night-time lights. The moment your leave the front door you'll have famous shops, on point drinks, amazing food, Wisconsin ice cream, retro candy, coffee shop, and much more! 10 minutes from Green Lake! 30 minutes from Oshkosh and Fond du Lac. Less than 90 minutes away from Appleton, Green Bay, Madison, Milwaukee, etc.

Sep 5 – 12

G$25,747 GYD per night

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!

Feb 6 – 13

G$25,901 GYD per night

Home in Campbellsport

4.99 out of 5 average rating, 135 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!

Nov 11 – 18

G$26,711 GYD per night

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*.

Feb 28 – Mar 7

G$38,328 GYD per night

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.

Aug 8 – 15

G$31,150 GYD per night

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!

Feb 8 – 15

G$27,771 GYD per night

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.

Jan 5 – 12

G$22,994 GYD per night

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.

Oct 28 – Nov 4

G$16,652 GYD per night

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Other great vacation rentals in Waupun

Cottage in Beaver Dam

4.95 out of 5 average rating, 19 reviews

Cozy lakeside getaway

Nov 27 – Dec 4

G$37,103 GYD per night

Farm stay in Burnett

4.91 out of 5 average rating, 22 reviews

Marsh Haven by Fieldview Estates

May 27 – Jun 3

G$39,863 GYD per night

Home in Fond du Lac

4.84 out of 5 average rating, 19 reviews

Woltring Waters Waterfront Home

Sep 27 – Oct 4

G$28,462 GYD per night

Home in Fond du Lac

4.91 out of 5 average rating, 53 reviews

Country home with fireplace, sauna & putting green

Sep 1 – 8

G$35,416 GYD per night

Cottage in Princeton

4.9 out of 5 average rating, 67 reviews

Charming Country Cottage on Too Much Joy Homestead

Jan 19 – 26

G$25,788 GYD per night

Home in Markesan

5.0 out of 5 average rating, 59 reviews

The Retro Retreat near Green Lake in Amish Country

Aug 6 – 13

G$27,697 GYD per night

Apartment in Mayville

5.0 out of 5 average rating, 10 reviews

Spacious 2 bedroom Apartment on river

Apr 24 – May 1

G$35,416 GYD per night

Cottage in Randolph

4.93 out of 5 average rating, 29 reviews

Quiet Cottage on Beaver Dam Lake

Nov 24 – Dec 1

G$45,432 GYD per night

Destinations to explore