A vast agricultural landscape with fields, roads, and scattered buildings under a clear sky.

Holiday Homes in Chilton

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chilton holiday homes

A wooden sign with "Woodland Cottage" written on it, surrounded by potted flowers and greenery.

1. 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, (181 reviews)
"We stay there every year and are never disappointed. Great location and experience. Thank you!"
United States
Doug S.
The price is NZ$577
includes taxes & fees
5 Oct - 6 Oct
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
A wooden deck with a bench, a door with frosted glass, and two wall-mounted lights.

2. Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Reedsville
9.8 out of 10, Exceptional, (35 reviews)
"Our 4th time here. Great stay as always."
United States
Jason R.
The price is NZ$816
includes taxes & fees
28 Sept - 29 Sept
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
A wooden deck with a Char-Broil grill, overlooking a body of water.

3. Lakefront Cottage on Lake Winnebago

Lakefront Cottage on Lake Winnebago
Hilbert
9.6 out of 10, Exceptional, (9 reviews)
"Liked the fire pits and the view "
United States
Mark M.
The price is NZ$682
includes taxes & fees
4 Oct - 5 Oct
Lakefront Cottage on Lake Winnebago
A cabin with a deck, a covered porch, and a paved driveway.

4. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (70 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
The price is NZ$483
includes taxes & fees
29 Sept - 30 Sept
The Esker Ridge Chalet, Pristine Elkhart Solitude
A hotel room with two beds, a dining area, and a view of the outdoors.

5. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is NZ$314
includes taxes & fees
19 Oct - 20 Oct
Victorian Inn #241 | 2 Queen Beds
A spacious lobby with leather sofas, a chandelier, a large TV, and a foosball table.

6. 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 Kohler
Kiel
8.8 out of 10, Excellent, (6 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."
United States
Ryan K.
The price is NZ$912
includes taxes & fees
23 Oct - 24 Oct
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
A room with a hanging chair, a dining area, and a view of the outdoors.

7. Cozy Oshkosh Home Minutes from UW, EAA & Downtown

Cozy Oshkosh Home Minutes from UW, EAA & Downtown
Oshkosh
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."
United States
Tonia G.
The price is NZ$824
includes taxes & fees
28 Sept - 29 Sept
Cozy Oshkosh Home Minutes from UW, EAA & Downtown
A house with a front yard, a dock, and a small body of water.

8. Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly

Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly
Oshkosh
9.8 out of 10, Exceptional, (36 reviews)
"Very nice stay, well accommodating."
United States
Chris S.
The price is NZ$612
includes taxes & fees
4 Oct - 5 Oct
Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly
An outdoor patio with a metal fire table, a chair, and a white fence with string lights.

9. Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago

Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago
Oshkosh
9.6 out of 10, Exceptional, (4 reviews)
"This was the perfect short-notice getaway for us. Pet friendly, extra quiet neighborhood, close to everything. Check in was a breeze, the place was clean. I am verry happy with our stay."
United States
Charles W.
The price is NZ$527
includes taxes & fees
27 Sept - 28 Sept
Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago
A wooden front door with a number plate, a mailbox, and a small porch with steps leading up to it.

10. Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago

Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago
Oshkosh
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 ."
United States
Michael B.
The price is NZ$650
includes taxes & fees
26 Sept - 27 Sept
Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago
A spacious living room with hardwood floors, a large potted plant, a hanging chair, and a dining area with a patterned rug.

11. 2 Min to Downtown Appleton! 4BD/2BA

2 Min to Downtown Appleton! 4BD/2BA
Appleton
9.8 out of 10, Exceptional, (37 reviews)
"Nice location to lots of sites. Good communications. Fewer check-out requirements compared to other properties. We'd stay again. "
United States
Ross S.
The price is NZ$796
includes taxes & fees
27 Sept - 28 Sept
2 Min to Downtown Appleton! 4BD/2BA
A living room with two grey sofas, a black coffee table, and a white door.

12. Oshkosh's #1 Home Away From Home

Oshkosh's #1 Home Away From Home
Oshkosh
The price is NZ$616
includes taxes & fees
4 Oct - 5 Oct
Oshkosh's #1 Home Away From Home
A kitchen with white cabinets, a wooden floor, and a hanging plant.

13. 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
9.8 out of 10, Exceptional, (19 reviews)
"The throwback vibes in this house were wonderful. Very clean and close enough to College Avenue that we didn’t drive anywhere once we got to the house. We were able to walk everywhere we wanted to. Overall it was a great experience!"
United States
Jeff U.
The price is NZ$395
includes taxes & fees
13 Oct - 14 Oct
Historic City Park home within walking distance to all downtown has to offer!
A living room with a television, a coffee table, a sofa, a chair, and a staircase.

14. Steps from Downtown

Steps from Downtown
Appleton
9.8 out of 10, Exceptional, (64 reviews)
"We loved staying in this beautiful and comfortable home! Our hosts thought of everything we might need and were very responsive when we had a question. We would highly recommend renting this property!"
United States
Michelle G.
The price is NZ$677
includes taxes & fees
6 Oct - 7 Oct
Steps from Downtown
A modern living room with a sectional sofa, a wooden coffee table, and a futsal table.

15. 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, (66 reviews)
"Loved this place. Was able to walk to local businesses. Would definitely book again"
United States
Anonymous traveller
The price is NZ$792
includes taxes & fees
13 Oct - 14 Oct
Hang out at The Hangar! Newly remodeled, beautiful home, fully furnished.
A kitchen with white cabinets, a black stove, and a wooden floor.

16. Cozy Retreat • Fireplace Loft •Walk to Park & Lake

Cozy Retreat • Fireplace Loft •Walk to Park & Lake
Oshkosh
9.6 out of 10, Exceptional, (14 reviews)
"Was a great place for our Oshkosh fly in stay! "
United States
William N.
The price is NZ$828
includes taxes & fees
26 Sept - 27 Sept
Cozy Retreat • Fireplace Loft •Walk to Park & Lake
A flat-screen TV mounted on a wall above a wooden entertainment center with a fireplace below.

17. Pac-Man House: Spacious 4-bedroom house in charming Oshkosh

Pac-Man House: Spacious 4-bedroom house in charming Oshkosh
Oshkosh
10.0 out of 10, Exceptional, (10 reviews)
"Very clean, thoughtfully decorated, really great spot overall. Would definitely book again."
United States
Andy D.
The price is NZ$859
includes taxes & fees
5 Oct - 6 Oct
Pac-Man House: Spacious 4-bedroom house in charming Oshkosh
A kitchen with wooden cabinets, a sink, and a window.

18. Cozy 1-bedroom house w/ Washer and dryer available

Cozy 1-bedroom house w/ Washer and dryer available
Fond du Lac
8.8 out of 10, Excellent, (3 reviews)
"Priced high due to EAA week. Only about 20 minutes from Oshkosh. Very clean."
United States
Leslie W.
The price is NZ$400
includes taxes & fees
4 Oct - 5 Oct
Cozy 1-bedroom house w/ Washer and dryer available
A dining area with a wooden board displaying various cheeses, meats, and fruits, and two glasses of red wine.

19. 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 Dogs
Menasha
9.6 out of 10, Exceptional, (37 reviews)
"Great place to stay. Peaceful and clean."
United States
Josh W.
The price is NZ$1,081
includes taxes & fees
28 Sept - 29 Sept
Lux Designer Lakefront Home with Views, Firepit, Dock, Kayaks, and up to 2 Dogs
A hallway with a dark wall, a mirror, a wicker chair, a sofa, and a plant.

20. Roomy Central Hub • Games, Fire Pit & Downtown Fun

Roomy Central Hub • Games, Fire Pit & Downtown Fun
Oshkosh
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!"
United States
Matthew D.
The price is NZ$1,662
includes taxes & fees
26 Sept - 27 Sept
Roomy Central Hub • Games, Fire Pit & Downtown Fun
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 Chilton Hotel Reviews

Cobblestone Hotel & Suites - Appleton International Airport

Cobblestone Hotel & Suites - Appleton International Airport

10/10 Excellent
"Great property"
Olden 2-night trip
Posted 2 hours ago
Cobblestone Hotel & Suites - Appleton International Airport

Find out more about Chilton

Chilton Holiday Homes information

Number of reviews
526
Accommodation
454 Holiday Homes
Lowest Price
NZ$314
Highest Price
NZ$1,081