A snow-covered pier with a lighthouse in the background.

Winnebago County Holiday Rentals

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Our top choices for Winnebago County holiday rentals

A modern, compact bedroom with a large bed and a wooden nightstand. Adjacent is a kitchenette with dark cabinets, a microwave, and a refrigerator.

1. Unit 11 Fox Flats Studios @ Neenah, WI

Unit 11 Fox Flats Studios @ Neenah, WI
Neenah
6.0 out of 10, (2 reviews)
"The worst place I’ve ever stayed in. Bad spider and mosquitoe problems also they had the cleaner lady trying to rush and clean the place 5 minutes before I showed up. Close by barking from other dogs distracted much needed sleep for work the next day. I don’t recommend this place at all. Made me have second thoughts about relocating to Wisconsin"
United States
Bernard L.
The price is AU$259
includes taxes & fees
11 Nov - 12 Nov
Unit 11 Fox Flats Studios @ Neenah, WI
A two-story house with a front porch, a small staircase, and a picket fence.

2. Cozy Oshkosh House with Piano

Cozy Oshkosh House with Piano
Oshkosh
8.2 out of 10, Very good, (11 reviews)
"Very nice"
United States
Marshall T.
The price is AU$473
includes taxes & fees
12 Nov - 13 Nov
Cozy Oshkosh House with Piano
A living room with two grey sofas, a black coffee table, and a white door.

3. Oshkosh's #1 Home Away From Home

Oshkosh's #1 Home Away From Home
Oshkosh
The price is AU$485
includes taxes & fees
7 Dec - 8 Dec
Oshkosh's #1 Home Away From Home
A multi-story hotel with a central courtyard, parking lot, and a view of the surrounding urban area.

4. Downtown Chic Retreat | Sleeps 4

Downtown Chic Retreat | Sleeps 4
Neenah
8.0 out of 10, Very good, (1 review)
"There is a loose screw on the cupboard to the trash--the cupboard door is going to fall off. Also the conditioner dispenser in the shower is not working. We had a very nice weekend."
United States
Greg A.
Downtown Chic Retreat | Sleeps 4
A historic building with a prominent 'GRAND' sign, large windows, and a tree in front.

5. Opera House Square Loft | Sleeps 6

Opera House Square Loft | Sleeps 6
Oshkosh
9.0 out of 10, Wonderful, (2 reviews)
"Traveled with our two adult sons and we all loved this place. Incredibly convenient and a unique property. Yes, there is noise from the downtown area, but it didn't keep us up and it wasn't intrusive. It's part of being in the heart of the city. We would stay there again."
United States
Peggy L.
The price is AU$544
includes taxes & fees
11 Nov - 12 Nov
Opera House Square Loft | Sleeps 6
A neatly made bed with a white and black color scheme, a small bedside table with a plant, and a bookshelf with books and a plant.

6. Luxury In A Quaint Little Package

Luxury In A Quaint Little Package
Oshkosh
8.0 out of 10, Very good, (13 reviews)
"Very clean and had a whole lot of extra amenities at no extra charge. Would definitely stay at that location again."
United States
Scott B.
The price is AU$274
includes taxes & fees
11 Nov - 12 Nov
Luxury In A Quaint Little Package
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 AU$680
includes taxes & fees
11 Nov - 12 Nov
Cozy Oshkosh Home Minutes from UW, EAA & Downtown
A neatly made bed with white linens and a brown throw blanket, flanked by two bedside lamps with exposed bulbs.

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

Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago
Oshkosh
9.2 out of 10, Wonderful, (5 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 AU$381
includes taxes & fees
1 Dec - 2 Dec
Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago
A compact living space with a kitchenette, a sofa, a coffee table, and a dining area.

9. The Big Blue Jay on winneconne

The Big Blue Jay on winneconne
Winneconne
9.6 out of 10, Exceptional, (5 reviews)
"Very clean, had everything we needed. Would stay stay again for sure. "
United States
Jim H.
The price is AU$405
includes taxes & fees
13 Nov - 14 Nov
The Big Blue Jay on winneconne
A house with a front yard, a dock, and a small body of water.

10. 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, (39 reviews)
"Very nice stay, well accommodating."
United States
Chris S.
The price is AU$493
includes taxes & fees
2 Dec - 3 Dec
Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly
A single-story house with a garage, a front yard with a lawn and a small garden, and a driveway leading to the garage.

11. Beautiful House by the Lake ~ Incredible Sunset ~ With Hot Tub!

Beautiful House by the Lake ~ Incredible Sunset ~ With Hot Tub!
Winneconne
9.6 out of 10, Exceptional, (415 reviews)
"This place was a great spot for our family's annual vacation. The location was perfect, small town feel while still living the lake life. The communication with the host with easy. Sunsets on the water were really great."
United States
Sara P.
The price is AU$436
includes taxes & fees
11 Nov - 12 Nov
Beautiful House by the Lake ~ Incredible Sunset ~ With Hot Tub!
A modern living room with a sectional sofa, a wooden coffee table, and a futsal table.

12. 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!"
United States
Mike B.
The price is AU$606
includes taxes & fees
22 Nov - 23 Nov
Hang out at The Hangar! Newly remodeled, beautiful home, fully furnished.
A cozy room with a sofa, two nightstands, a wooden coffee table, and a rustic wall.

13. 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 AU$493
includes taxes & fees
1 Dec - 2 Dec
Cozy Retreat • Fireplace Loft •Walk to Park & Lake
A wooden front door with a number plate, a mailbox, and a small porch with steps leading up to it.

14. 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 AU$516
includes taxes & fees
24 Nov - 25 Nov
Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago
A room with a large window overlooking a grassy area and a body of water. There is a chair, a blue bean bag, and a small table with a vase of flowers.

15. Charming cottage on Lake Winnebago

Charming cottage on Lake Winnebago
Neenah
10.0 out of 10, Exceptional, (60 reviews)
"Great communication and easy check in and check out. Would definitely recommend!"
United States
Jocelyn S.
The price is AU$708
includes taxes & fees
24 Nov - 25 Nov
Charming cottage on Lake Winnebago
A hallway with a dark wall, a mirror, a wicker chair, a sofa, and a plant.

16. 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 AU$1,371
includes taxes & fees
11 Nov - 12 Nov
Roomy Central Hub • Games, Fire Pit & Downtown Fun
A dining area with a wooden board displaying various cheeses, meats, and fruits, and two glasses of red wine.

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 Dogs
Menasha
9.6 out of 10, Exceptional, (38 reviews)
"Great place to stay. Peaceful and clean."
United States
Josh W.
The price is AU$861
includes taxes & fees
12 Nov - 13 Nov
Lux Designer Lakefront Home with Views, Firepit, Dock, Kayaks, and up to 2 Dogs
A modern kitchen with dark wood paneling, stainless steel appliances, and wooden shelves.

18. Sky & Stream Escape, EAA AirVenture Oasis

Sky & Stream Escape, EAA AirVenture Oasis
Oshkosh
10.0 out of 10, Exceptional, (1 review)
"We were pleasantly surprised at the decor and cleanliness of the property. Wished we could have stayed longer! Host was quick to respond to any questions we had!"
United States
Kathy B.
The price is AU$825
includes taxes & fees
11 Nov - 12 Nov
Sky & Stream Escape, EAA AirVenture Oasis
A grand staircase with a wooden handrail and a chandelier above.

19. Entire Victorian Mansion - Near Main St & Farmer’s Mkt - Sleeps12

Entire Victorian Mansion - Near Main St & Farmer’s Mkt - Sleeps12
Oshkosh
10.0 out of 10, Exceptional, (44 reviews)
"Amazing property with such charm, perfect for our work retreat "
United States
Angela Z.
The price is AU$957
includes taxes & fees
24 Nov - 25 Nov
Entire Victorian Mansion - Near Main St & Farmer’s Mkt - Sleeps12
A living room with a sofa, a TV, a ceiling fan, and a view of the outdoors.

20. World Series 80 miles, EAA 8 miles,Packers 39 miles

World Series 80 miles, EAA 8 miles,Packers 39 miles
Oshkosh
The price is AU$801
includes taxes & fees
11 Nov - 12 Nov
World Series 80 miles, EAA 8 miles,Packers 39 miles
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 Winnebago County Hotel Reviews

Cobblestone Hotel & Suites - Appleton International Airport

Cobblestone Hotel & Suites - Appleton International Airport

8/10 Good
"The room was clean and neat."
Ruth 2-night trip
Posted 13 hours ago
Cobblestone Hotel & Suites - Appleton International Airport

Find out more about Winnebago County

Everything you need to know about Winnebago County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winnebago County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winnebago County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winnebago County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winnebago County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winnebago County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Winnebago County holiday rentals we have chosen for you start as low as AU$381 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Winnebago County rentals

At Expedia, we put the best Winnebago County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winnebago County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winnebago County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winnebago County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.