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Our top choices for Chilton holiday homes
1. Lakefront Cottage on Lake Winnebago
Lakefront Cottage on Lake WinnebagoHilbert
9.8 out of 10, Exceptional, (12 reviews)
"Liked the fire pits and the view "
Mark M.
The price is NZ$595
includes taxes & fees
10 Nov - 11 Nov
2. Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!New Holstein
10.0 out of 10, Exceptional, (182 reviews)
"We stay there every year and are never disappointed. Great location and experience. Thank you!"
Doug S.
The price is NZ$572
includes taxes & fees
15 Nov - 16 Nov
3. Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and KohlerKiel
9.0 out of 10, Wonderful, (7 reviews)
"This is an amazing and fun property. If you are in town for any event at Road America it makes it a little more special."
Ryan K.
The price is NZ$819
includes taxes & fees
10 Nov - 11 Nov
4. The Esker Ridge Chalet, Pristine Elkhart Solitude
The Esker Ridge Chalet, Pristine Elkhart SolitudeElkhart Lake
10.0 out of 10, Exceptional, (73 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
Barbara
The price is NZ$466
includes taxes & fees
10 Nov - 11 Nov
5. Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road AmericaReedsville
9.8 out of 10, Exceptional, (36 reviews)
"Our 4th time here. Great stay as always."
Jason R.
The price is NZ$822
includes taxes & fees
10 Nov - 11 Nov
6. Victorian Inn #241 | 2 Queen Beds
Victorian Inn #241 | 2 Queen BedsElkhart Lake
The price is NZ$312
includes taxes & fees
10 Nov - 11 Nov
7. Fox River Overlook | Sleeps 11 | Fire Pit
Fox River Overlook | Sleeps 11 | Fire PitKaukauna
10.0 out of 10, Exceptional, (2 reviews)
"Great stay and location."
Cody W.
The price is NZ$803
includes taxes & fees
10 Nov - 11 Nov
8. Road America, Elkhart Lake!
Road America, Elkhart Lake!Elkhart Lake
7.0 out of 10, Good, (2 reviews)
The price is NZ$659
includes taxes & fees
8 Dec - 9 Dec
9. Cozy Oshkosh Home Minutes from UW, EAA & Downtown
Cozy Oshkosh Home Minutes from UW, EAA & DowntownOshkosh
10.0 out of 10, Exceptional, (2 reviews)
"This house is very cute and very vibrant. The host was amazing and very accommodating. I had a very easy check in and check out."
Tonia G.
The price is NZ$915
includes taxes & fees
10 Nov - 11 Nov
10. Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly
Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog FriendlyOshkosh
9.8 out of 10, Exceptional, (39 reviews)
"Very nice stay, well accommodating."
Chris S.
The price is NZ$618
includes taxes & fees
1 Dec - 2 Dec
11. Cozy Retreat • Fireplace Loft •Walk to Park & Lake
Cozy Retreat • Fireplace Loft •Walk to Park & LakeOshkosh
9.6 out of 10, Exceptional, (14 reviews)
"Was a great place for our Oshkosh fly in stay! "
William N.
The price is NZ$651
includes taxes & fees
16 Nov - 17 Nov
12. Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago
Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake WinnebagoOshkosh
10.0 out of 10, Exceptional, (4 reviews)
"We had a great time staying herePlenty of room to hang out inAnd for us it easily slept 4 adults Location was close to grocerys / resteraunts etc ."
Michael B.
The price is NZ$649
includes taxes & fees
10 Nov - 11 Nov
13. Indoor Pool-Golf Simulator-RaceCar Simulator-HotTub-Movie Theatre-PoolTables
Indoor Pool-Golf Simulator-RaceCar Simulator-HotTub-Movie Theatre-PoolTablesFond du Lac
The price is NZ$6,036
includes taxes & fees
10 Nov - 11 Nov
14. 2 Min to Downtown Appleton! 4BD/2BA
2 Min to Downtown Appleton! 4BD/2BAAppleton
9.6 out of 10, Exceptional, (40 reviews)
"Great place and was a great stay. Would recommend as Nichole and team were responsive and helpful. Would definitely stay here again. "
Stephen P.
The price is NZ$766
includes taxes & fees
10 Nov - 11 Nov
15. Historic City Park home within walking distance to all downtown has to offer!
Historic City Park home within walking distance to all downtown has to offer!Appleton
10.0 out of 10, Exceptional, (22 reviews)
"Nice, comfortable place easy location access to anything you want"
Matthew M.
The price is NZ$388
includes taxes & fees
16 Nov - 17 Nov
16. Third Ward Historic Mansion | Sleeps 13
Third Ward Historic Mansion | Sleeps 13Appleton
9.2 out of 10, Wonderful, (7 reviews)
"Beautiful property but steps are a major concern and not kid friendlyNeeds more railing on the third level and block off basement steps since they are of no use to visitors. Great yard for play and lovely neighborhood for walks"
mary beth r.
The price is NZ$912
includes taxes & fees
10 Nov - 11 Nov
17. Lux Designer Lakefront Home with Views, Firepit, Dock, Kayaks, and up to 2 Dogs
Lux Designer Lakefront Home with Views, Firepit, Dock, Kayaks, and up to 2 DogsMenasha
9.6 out of 10, Exceptional, (38 reviews)
"Great place to stay. Peaceful and clean."
Josh W.
The price is NZ$1,117
includes taxes & fees
12 Nov - 13 Nov
18. Oshkosh's #1 Home Away From Home
Oshkosh's #1 Home Away From HomeOshkosh
The price is NZ$751
includes taxes & fees
8 Dec - 9 Dec
19. Hang out at The Hangar! Newly remodeled, beautiful home, fully furnished.
Hang out at The Hangar! Newly remodeled, beautiful home, fully furnished.Oshkosh
9.6 out of 10, Exceptional, (71 reviews)
"Great host and great location for EAA. Perfect size for us…six adults, two of them working remotely!"
Mike B.
The price is NZ$761
includes taxes & fees
22 Nov - 23 Nov
20. Roomy Central Hub • Games, Fire Pit & Downtown Fun
Roomy Central Hub • Games, Fire Pit & Downtown FunOshkosh
10.0 out of 10, Exceptional, (1 review)
"Host were very accommodating to everything my group needed. Quick communications, great location, and plenty of room!"
Matthew D.
The price is NZ$1,705
includes taxes & fees
10 Nov - 11 Nov
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.
Learn more about Chilton
Cheese lovers flock to the Henning's Cheese Factory for tours and tastings of award-winning Wisconsin cheese. Explore the Calumet County Park's hiking trails or rent kayaks to paddle the peaceful waters of Lake Winnebago.
