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Oshkosh Holiday Rentals

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Holiday Rentals in Oshkosh

Hot tub - 4 Bedroom - 3.5 Bathrooms - Perfect Location

10.0 out of 10, Exceptional, (24)
"Place was gorgeous! Location was perfect! Host was great with communication!"
Hot tub - 4 Bedroom - 3.5 Bathrooms - Perfect Location

Retreat on Lake Winnebago

9.8 out of 10, Exceptional, (124)
"This property was amazing. It had so many nice extras! Kitchen had most things I have at home. Katie is an amazing host and always responded quickly prior to staying at her property. We would definitely stay again. The property is so relaxing and peaceful. Also very friendly neighbors "
Retreat on Lake Winnebago

Lakefront 2-bed house in Oshkosh with dock!

10.0 out of 10, Exceptional, (33)
"This property is absolutely fantastic. Great location, comfortable bedding, and a gorgeous lake"
Lakefront 2-bed house in Oshkosh with dock!

Cabin Oasis on Lake Winnebago "Minutes from EAA"

10.0 out of 10, Exceptional, (28)
"Staying at this cabin exceeded our expectations. The location was perfect, the cabin cozy and clean, and our host “Josh” was fantastic - went above and beyond. Our stay was magnificent. We highly recommend staying here!"
Cabin Oasis on Lake Winnebago "Minutes from EAA"

Late Summer Retreat • Firepit • Lake • Downtown!

9.6 out of 10, Exceptional, (12)
"Very nice and quiet stay with a great view of the lake!"
The price is NZ$681
includes taxes & fees
6 Oct - 7 Oct
Late Summer Retreat • Firepit • Lake • Downtown!

Luxury In A Quaint Little Package

8.0 out of 10, Very good, (9)
"Very comfy and cozy inside. Great lock safety. I will stay again."
The price is NZ$209
includes taxes & fees
13 Oct - 14 Oct
Luxury In A Quaint Little Package

Hickory On The Lake- Beautiful home on Lake Winnebago

9.6 out of 10, Exceptional, (20)
"Definitely booking again beautiful place"
The price is NZ$979
includes taxes & fees
6 Oct - 7 Oct
Hickory On The Lake- Beautiful home on Lake Winnebago

Downtown Tiny Home - Oshkosh

9.4 out of 10, Exceptional, (20)
"Our stay was great and the property was perfect for our trip!"
Downtown Tiny Home - Oshkosh

Chill Lake Channel 'Brewhouse' Townhouse: 2 bedrooms on Lake Winnebago

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 ."
The price is NZ$649
includes taxes & fees
3 Oct - 4 Oct
Chill Lake Channel 'Brewhouse' Townhouse: 2 bedrooms on Lake Winnebago

Hang out at The Hangar! Newly remodeled, beautiful home, fully furnished.

9.6 out of 10, Exceptional, (48)
"Our team had a great time! The place was clean, organized, and in a great area! We would definitely stay again!"
The price is NZ$679
includes taxes & fees
16 Oct - 17 Oct
Hang out at The Hangar! Newly remodeled, beautiful home, fully furnished.

WolfDen Getaway-Winnebago Channel

10.0 out of 10, Exceptional, (81)
"Everything was perfect, hosts were very responsive and helpful! "
WolfDen Getaway-Winnebago Channel

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

2.0 star property
9.0 out of 10, Wonderful, (2)
"Nice, clean property. "
The price is NZ$504
includes taxes & fees
5 Oct - 6 Oct
Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago

La Petit Maison - Lakefront Oshkosh Home!

3.0 star property
La Petit Maison - Lakefront Oshkosh Home!

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

10.0 out of 10, Exceptional, (33)
"We had an excellent stay at the doe house. Becky was so accommodating and the house was perfect for our bachelorette weekend in Oshkosh. "
The price is NZ$1,361
includes taxes & fees
6 Oct - 7 Oct
Entire Victorian Mansion - Near Main St & Farmer’s Mkt - Sleeps12

The Alex Furnished Rentals

3.0 star property
10.0 out of 10, Exceptional, (1)
"If I could give them 10 stars I would. Communication was excellent and prompt. If not right away it was just a few minutes. Apartment was super nice, so welcoming and comfortable. Location is easy to get to, close enough to entertainment yet far enough away to have the peace and quiet for a relaxing wind down. Well equipped apartment with the basics plus a couple of special touches just to make you feel cared for. Highly recommend this place and the company."
The Alex Furnished Rentals

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

10.0 out of 10, Exceptional, (67)
"Awesome place! Emily is a great host and all instructions were extremely clear!"
Lakefront! Huge Game RM + Chefs Kitchen! Sleep 40!

Beautiful Lakefront Home ~ Outstanding Sunsets ~ Includes Hot Tub!

9.6 out of 10, Exceptional, (368)
"We had a great lowkey girls' weekend at this lakehouse! The house had everything we needed and the water was great to swim and hang out in. Thanks for a great stay!"
The price is NZ$534
includes taxes & fees
15 Oct - 16 Oct
Beautiful Lakefront Home ~ Outstanding Sunsets ~ Includes Hot Tub!

Spacious water front property located on Big Green Lake

9.6 out of 10, Exceptional, (54)
"Great location!"
Spacious water front property located on Big Green Lake

Historical Haven Steps to Downtown

10.0 out of 10, Exceptional, (2)
"The property is adorable. The host is warm and accommodating. The condo is adorable and very homey."
The price is NZ$447
includes taxes & fees
9 Oct - 10 Oct
Historical Haven Steps to Downtown

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

4.0 star property
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 ."
The price is NZ$5,636
includes taxes & fees
8 Oct - 9 Oct
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
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

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 favorite 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 depends 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 NZ$209 per night. Entering your travel dates in the search wizard you might find 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 Pollock Community Water Park, 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?

Retreat on Lake Winnebago: This highly rated holiday home rental in Oshkosh is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease 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. You can relax into your holiday with a garden and a selection of games. Some other top choices in Oshkosh are Lakefront 2-bed house in Oshkosh with dock! and Charming 3-bedroom house on a farmette with AC and WiFi in delightful Oshkosh..

How many holiday rentals will I find in Oshkosh?

With 304 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.