Waupun Holiday Rentals

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Check prices for these dates

Tonight
18 Dec - 19 Dec
Tomorrow
19 Dec - 20 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Waupun holiday rentals

Property grounds
Lakefront! Huge Game RM + Chefs Kitchen! Sleep 40!

Lakefront! Huge Game RM + Chefs Kitchen! Sleep 40!

Lakefront! Huge Game RM + Chefs Kitchen! Sleep 40!
Markesan
10.0 out of 10, Exceptional, (70)
"Everything was as advertised for a tremendous stay for 16 guy golf trip. More beds than we could use and the first floor kitchen/dining/living space combined with the activities in the basement kept our group entertained. Highly recommended."
United States
William G.
Lakefront! Huge Game RM + Chefs Kitchen! Sleep 40!
Smart TV, fireplace, video games
Hot tub - 4 Bedroom - 3.5 Bathrooms - Perfect Location

Hot tub - 4 Bedroom - 3.5 Bathrooms - Perfect Location

Hot tub - 4 Bedroom - 3.5 Bathrooms - Perfect Location
Oshkosh
10.0 out of 10, Exceptional, (27)
"We had an excellent stay. The place was clean and hot tub was warmed up for us upon arrival. Check-in/out was seamless. The game room was a great place to hang out with friends. "
United States
Matt B.
Hot tub - 4 Bedroom - 3.5 Bathrooms - Perfect Location
Property grounds
Lake Winnebago Waterfront Cottage W/Hot Tub [2 King; 1 Queen]

Lake Winnebago Waterfront Cottage W/Hot Tub [2 King; 1 Queen]

Lake Winnebago Waterfront Cottage W/Hot Tub [2 King; 1 Queen]
Fond du Lac
9.8 out of 10, Exceptional, (168)
"Absolutely amazing stay. Wonderful home. Fantastic owners. A++++++"
United States
Louis
Lake Winnebago Waterfront Cottage W/Hot Tub [2 King; 1 Queen]
Exterior
Spacious water front property located on Big Green Lake

Spacious water front property located on Big Green Lake

Spacious water front property located on Big Green Lake
Green Lake
9.6 out of 10, Exceptional, (56)
"outstanding location, both houses were fantastic"
United States
bud z.
Spacious water front property located on Big Green Lake
Terrace/patio
Retreat on Lake Winnebago

Retreat on Lake Winnebago

Retreat on Lake Winnebago
Oshkosh
9.8 out of 10, Exceptional, (127)
"Very well appointed. Everything we needed. Communication was great. The view was fantastic. "
United States
Anonymous traveller
Retreat on Lake Winnebago
Property grounds
Country home with flowing river

Country home with flowing river

Country home with flowing river
Pardeeville
9.0 out of 10, Wonderful, (159)
"Everything was excellent! Extremely clean. We were in town to visit family and it was perfect for our needs. Nice little bench next to the river."
United States
Kristen G.
The price is HK$1,081
HK$1,305 total
includes taxes & fees
19 Dec - 20 Dec
Country home with flowing river
TV, DVD player
Beautiful 2 Bedroom Duplex

Beautiful 2 Bedroom Duplex

Beautiful 2 Bedroom Duplex
Fond du Lac
9.8 out of 10, Exceptional, (16)
"Nice house and easy to find"
United States
Mary G.
The price is HK$1,081
HK$2,241 total
includes taxes & fees
6 Jan - 7 Jan 2026
Beautiful 2 Bedroom Duplex
Aerial view
The Little Lake House - Private/Secluded Pennisula - Lake Winnebago

The Little Lake House - Private/Secluded Pennisula - Lake Winnebago

The Little Lake House - Private/Secluded Pennisula - Lake Winnebago
Fond du Lac
9.0 out of 10, Wonderful, (74)
"Very clean. Only recommend maybe a luggage rack in bathroom area or hooks there to hang our towels or clothes while getting ready. Maybe a heads up on the grill. Thought it was gas but actually charcoal. All in all, we can always find something WE would do but it was a wonderful stay. It was so lovely to wake up every morning to the beautiful sunrise, the peace, just the beauty of the peninsula. Craig was very responsive when we had a question about something. We would love to stay again. Its...
United States
JULIE & STEVE N.
The Little Lake House - Private/Secluded Pennisula - Lake Winnebago
Terrace/patio
The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!

The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!

The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!
2.0 star property
Beaver Dam
10.0 out of 10, Exceptional, (18)
"A beautiful home in a peaceful setting. Well appointed, everything we needed and more for a stress free relaxing getaway. Thank you Doug for the wonderful experience."
United States
Marjean P.
The price is HK$1,455
HK$3,883 total
includes taxes & fees
13 Jan - 14 Jan 2026
The Gatsby Getaway - A Charming 100-Year-Old Lakeside Retreat in Beaver Dam!
Dining
Perfect Lake House to gather with Friends and Family. Come make some memories!!

Perfect Lake House to gather with Friends and Family. Come make some memories!!

Perfect Lake House to gather with Friends and Family. Come make some memories!!
Oshkosh
9.0 out of 10, Wonderful, (14)
"Comfortable home in a great location"
United States
Rosa R.
Perfect Lake House to gather with Friends and Family. Come make some memories!!
Property grounds
Lakefront Cabin! Arcades, Putt Putt, Close to Golf

Lakefront Cabin! Arcades, Putt Putt, Close to Golf

Lakefront Cabin! Arcades, Putt Putt, Close to Golf
Markesan
9.6 out of 10, Exceptional, (33)
"Very nice place with tons of space for the group to spread out or be together. If you're coming with family, there are endless options for all ages."
United States
Brock P.
The price is HK$5,530
HK$11,465 total
includes taxes & fees
29 Dec - 30 Dec
Lakefront Cabin! Arcades, Putt Putt, Close to Golf
Property grounds
4 Bdrm 4 Bath Lake front Lake Sinissippi home

4 Bdrm 4 Bath Lake front Lake Sinissippi home

4 Bdrm 4 Bath Lake front Lake Sinissippi home
Juneau
10.0 out of 10, Exceptional, (43)
"Great property. Lots to do at the house. Plenty of space. "
United States
Justin R.
4 Bdrm 4 Bath Lake front Lake Sinissippi home
Interior
WolfDen Getaway-Winnebago Channel

WolfDen Getaway-Winnebago Channel

WolfDen Getaway-Winnebago Channel
Oshkosh
10.0 out of 10, Exceptional, (86)
"Very nice accommodations. Clean and neat. Will definately stay again."
United States
Dennis S.
WolfDen Getaway-Winnebago Channel
Interior
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater

Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater

Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
4.0 star property
Fond du Lac
10.0 out of 10, Exceptional, (1)
"Our large family had a magical Christmas! Our beautifully decorated rented home had everything we needed . We were all very comfortable during the day and night time sleeping . We had private spaces and family get together areas ."
United States
Brenda J.
The price is HK$15,559
HK$27,435 total
includes taxes & fees
5 Jan - 6 Jan 2026
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
Exterior
Indoor Pool-Golf Simulator-RaceCar Simulator-HotTub-Movie Theatre-Pool Tables

Indoor Pool-Golf Simulator-RaceCar Simulator-HotTub-Movie Theatre-Pool Tables

Indoor Pool-Golf Simulator-RaceCar Simulator-HotTub-Movie Theatre-Pool Tables
Fond du Lac
The price is HK$15,559
HK$41,315 total
includes taxes & fees
23 Dec - 24 Dec
Indoor Pool-Golf Simulator-RaceCar Simulator-HotTub-Movie Theatre-Pool Tables
Exterior
1880s Beauty! Family Fun. Walk to Downtown Green Lake, Heidel House & Golf!

1880s Beauty! Family Fun. Walk to Downtown Green Lake, Heidel House & Golf!

1880s Beauty! Family Fun. Walk to Downtown Green Lake, Heidel House & Golf!
Green Lake
10.0 out of 10, Exceptional, (34)
"Property was even better than described and was very clean. Had everything we needed. Overall an excellent stay. "
United States
David K.
1880s Beauty! Family Fun. Walk to Downtown Green Lake, Heidel House & Golf!
Exterior
Great location!

Great location!

Great location!
Green Lake
9.8 out of 10, Exceptional, (89)
"Beautiful property. Very well appointed home. "
United States
Carolyn M.
Great location!
Property grounds
4-bedroom house in peaceful Fond du Lac with AC Beautiful Lakefront property

4-bedroom house in peaceful Fond du Lac with AC Beautiful Lakefront property

4-bedroom house in peaceful Fond du Lac with AC Beautiful Lakefront property
Fond du Lac
10.0 out of 10, Exceptional, (1)
"Nice place and all as advertised."
United States
Charles B.
4-bedroom house in peaceful Fond du Lac with AC Beautiful Lakefront property
Property grounds
Serene Cottage with view of Green Lake

Serene Cottage with view of Green Lake

Serene Cottage with view of Green Lake
Green Lake
10.0 out of 10, Exceptional, (46)
"Clean house, close location to food and activities, quiet neighborhood."
United States
Anonymous traveller
Serene Cottage with view of Green Lake
Fridge, microwave, oven, stovetop
Modern Lake house on Lake winnebago

Modern Lake house on Lake winnebago

Modern Lake house on Lake winnebago
Oshkosh
10.0 out of 10, Exceptional, (11)
"Communication was great! The description was accurate and cleanliness was phenomenal! It was a great weekend house on the lake with much needed family time! "
United States
Kendi M.
Modern Lake house on Lake winnebago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Waupun Hotel Reviews

Cobblestone Suites Oshkosh

Cobblestone Suites Oshkosh

10/10 Excellent
"The room was warm, quiet, carpeted, the beds were extremely comfortable. "
Paul 2-night trip
Posted 4 days ago
Cobblestone Suites Oshkosh

Find out more about Waupun

Search for holiday rentals in Waupun on Expedia! You can easily find your home rentals, villas, holiday apartments in Waupun using one of the methods below:

  • View our selection of featured holiday rentals in Waupun
  • Use the map to find apartments and other holiday homes in the Waupun neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Waupun while they last

Look no further and take a look at our great range of rental properties in Waupun!

Frequently asked questions

Are there holiday rentals in Waupun?

Yes, there are holiday rentals close to the most popular sights in Waupun, or you can select a more secluded option if you're looking for a relaxing stay. Waupun is known for its restaurants and shopping. Make sure you have time to check out the golf courses and coffee shops during your trip.

What are some of the best holiday rentals that Waupun has to offer?

Lake Winnebago Waterfront Cottage W/Hot Tub [2 King; 1 Queen]: This holiday home rental outside of Waupun is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Waupun?

Expedia has 5 holiday rentals for your stay in Waupun.

What can I see and do in Waupun?

Shaler Memorial Park and Waupan Dog Park are a couple of scenic spots to enjoy the outdoors, whereas Waupun Heritage Museum is one of the cultural attractions. While here, Rock River Country Club and End of the Trail Statue are other places worth a visit.

What are holiday rentals like in Waupun?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Waupun. Holiday rentals offer amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.