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Oshkosh Holiday Rentals

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Our top choices for Oshkosh holiday rentals

7.6 out of 10, Good, (10)
"Very easy communication and good accommodations! Would recommend!"
United States
Brittany K.
The price is AU$253
includes taxes & fees
2 Jan - 3 Jan 2026
Luxury In A Quaint Little Package

Holiday Home in Oshkosh

Peaceful Home in Heart of Oshkosh!
10.0 out of 10, Exceptional, (21)
"Clean and simple home. Within walking distance of many restaurants and attractions"
United States
Erika B.
The price is AU$369
includes taxes & fees
30 Dec - 31 Dec
Peaceful Home in Heart of Oshkosh!
7.8 out of 10, Good, (7)
"What a beautiful home! We traveled to Osh Kosh to tour UWO and found this gem of a place to stay at! The neighbors were extremely nice as was the community. Very quiet neighborhood. The home had everything we needed and more! The host was wonderful in checking in with us throughout our stay, making sure we had all that we needed :)"
United States
JSN C.
Character Home on Harney - 3 bedroom, 2 bath
2.0 star property
The price is AU$1,583
includes taxes & fees
6 Jan - 7 Jan 2026
5 Min from University of Wisconsin – Oshkosh
10.0 out of 10, Exceptional, (3)
"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$572
includes taxes & fees
4 Jan - 5 Jan 2026
Chill Lake Channel 'Brewhouse' Townhouse: 2 bedrooms on Lake Winnebago
9.4 out of 10, Exceptional, (3)
"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$640
includes taxes & fees
29 Dec - 30 Dec
Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago
9.6 out of 10, Exceptional, (51)
"Nice place very accommodating "
United States
Linda M.
Hang out at The Hangar! Newly remodeled, beautiful home, fully furnished.
9.6 out of 10, Exceptional, (31)
"Such a beautiful stay, our kids had a blast on the lake and we all enjoyed our time! "
United States
Amanda S.
The price is AU$491
includes taxes & fees
25 Dec - 26 Dec
Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly
9.6 out of 10, Exceptional, (13)
"Was a great place for our Oshkosh fly in stay! "
United States
William N.
The price is AU$499
includes taxes & fees
6 Jan - 7 Jan 2026
Late Summer Retreat • Firepit • Lake • Downtown!
9.0 out of 10, Wonderful, (4)
"Great stay!"
United States
Brian L.
The price is AU$738
includes taxes & fees
4 Jan - 5 Jan 2026
Close to the big events in Oshkosh when you stay at Doty Landings
10.0 out of 10, Exceptional, (35)
"Amazing property with such charm, perfect for our work retreat "
United States
Angela Z.
The price is AU$1,190
includes taxes & fees
29 Dec - 30 Dec
Entire Victorian Mansion - Near Main St & Farmer’s Mkt - Sleeps12
10.0 out of 10, Exceptional, (1)
"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$581
includes taxes & fees
6 Jan - 7 Jan 2026
Sky & Stream Escape, EAA AirVenture Oasis
10.0 out of 10, Exceptional, (1)
"Brittany is a great host!Our group enjoyed our stay, the house is clean with plenty of space. Had everything we needed in the kitchen for cooking. Beds are comfy. Plenty of parking so no one had to park in the street. Our niece and nephew had fun playing games in the Pac-Man room. It snowed during our stay and Brittany came by twice to clear snow which was very nice. Nothing bad to say, everything was really good."
United States
Gary F.
The price is AU$442
includes taxes & fees
14 Jan - 15 Jan 2026
Pac-Man House: Spacious 4-bedroom house in charming Oshkosh
9.0 out of 10, Wonderful, (4)
"Clean, and convenient to everything we were looking for.Would rent it again the next time I’m in Oshkosh."
United States
Jim K.
The price is AU$725
includes taxes & fees
6 Jan - 7 Jan 2026
House blocks from the Fox River with access to Lake Winnebago. Easy I41 access.
3.0 star property
The price is AU$208
includes taxes & fees
26 Dec - 27 Dec
2 Mi to Lake Winnebago: Cozy Fond du Lac Studio
2.0 star property
10.0 out of 10, Exceptional, (4)
"Welcoming host with a great location and clean space!"
United States
Andrea L.
The price is AU$294
includes taxes & fees
30 Dec - 31 Dec
201 - Downtown 2 Bedroom Apartment
2.0 star property
10.0 out of 10, Exceptional, (2)
"Very clean, had everything we needed. Would stay stay again for sure. "
United States
Jim H.
The price is AU$339
includes taxes & fees
25 Dec - 26 Dec
The Big Blue Jay on winneconne
2.0 star property
8.0 out of 10, Very good, (1)
"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.
The price is AU$384
includes taxes & fees
30 Dec - 31 Dec
Luxury Downtown 2 Bedroom Flat
2.0 star property
10.0 out of 10, Exceptional, (1)
"It was exactly as advertised. Good value for a centrally located place"
United States
Keith N.
The price is AU$271
includes taxes & fees
7 Jan - 8 Jan 2026
Newly Renovated walk up apartment near everything
10.0 out of 10, Exceptional, (4)
"We were there for Apple fest and to visit with family "
United States
Pauline B.
The price is AU$355
includes taxes & fees
30 Dec - 31 Dec
Pinball Penthouse Luxury Downtown Flat
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 Oshkosh Hotel Reviews

Find out more about Oshkosh

Everything you need to know about Oshkosh 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 Oshkosh 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 Oshkosh holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oshkosh holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oshkosh. 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 Oshkosh 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 Oshkosh holiday rentals we have selected for you start as low as AU$253 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oshkosh rentals

At Expedia, we put the best Oshkosh 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 Oshkosh 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 Oshkosh 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 Oshkosh. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Oshkosh?

Yes, there are holiday rentals in Oshkosh close to Hughes Home Maid Chocolates, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts say Oshkosh is known for its museums and festivals. Allow some time to check out the shops during your trip.

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

Hot tub - 4 Bedroom - 3.5 Bathrooms - Perfect Location: This highly rated holiday home rental in Oshkosh offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Some other top choices in Oshkosh are Retreat on Lake Winnebago and Perfect Lake House to gather with Friends and Family. Come make some memories!!.

How many holiday rentals will I find in Oshkosh?

With 301 Expedia holiday rentals, you're guaranteed to find just the right place for your Oshkosh stay.

What can I see and do in Oshkosh?

Cultural attractions include Grand Opera House and Paine Art Center and Gardens, whereas Lake Winnebago and Ford Festival Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Menominee Nation Arena and Titan Stadium.

What are holiday rentals like in Oshkosh?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oshkosh. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family gatherings.