Photo by Vin Lane-Kieltyka
Oshkosh holiday homes
We found 738 holiday rentals — enter your dates for availability
Take a look at private holiday rentals within easy reach of Oshkosh, WI (OSH-Wittman Regional) that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a pool. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Oshkosh, WI (OSH-Wittman Regional)
Showing deals for:5 Sept - 12 Sept
Image gallery for Quiet home on a channel in Winneconne. Bring your boat!
1010 out of 10 rating
Exceptional
(22 reviews)
Quiet home on a channel in Winneconne. Bring your boat!
Winneconne, WI
8% off
Price is NZ$4,736
NZ$4,736
NZ$677 per night
includes taxes & fees
Image gallery for Ｄｅｓｔｉｎａｔｉｏｎ Ｄｏｗｎｔｏｗｎ
1010 out of 10 rating
Exceptional
(6 reviews)
Ｄｅｓｔｉｎａｔｉｏｎ Ｄｏｗｎｔｏｗｎ
Oshkosh, Wisconsin
7% off
Price is NZ$2,086
NZ$2,086
NZ$298 per night
includes taxes & fees
Image gallery for Stay right on the lake!
1010 out of 10 rating
Exceptional
(69 reviews)
Stay right on the lake!
Winneconne, WI
8% off
Price is NZ$4,443
NZ$4,443
NZ$635 per night
includes taxes & fees
Image gallery for Hot tub - 4 Bedroom - 3.5 Bathrooms - Perfect Location
1010 out of 10 rating
Exceptional
(20 reviews)
Hot tub - 4 Bedroom - 3.5 Bathrooms - Perfect Location
Oshkosh, WI
8% off
Price is NZ$5,956
NZ$5,956
NZ$851 per night
includes taxes & fees
Image gallery for Perfect Waterfront Retreat Destination on Lake Winnebago
1010 out of 10 rating
Exceptional
(17 reviews)
Perfect Waterfront Retreat Destination on Lake Winnebago
Oshkosh, WI
8% off
Price is NZ$3,477
NZ$3,477
NZ$497 per night
includes taxes & fees
Image gallery for Overlooking Lake Winnebago on EAA flight path
1010 out of 10 rating
Exceptional
(6 reviews)
Overlooking Lake Winnebago on EAA flight path
Oshkosh, WI
7% off
Price is NZ$4,086
NZ$4,086
NZ$584 per night
includes taxes & fees
Image gallery for 4 Bedroom Waterfront Home Available
1010 out of 10 rating
Exceptional
(9 reviews)
4 Bedroom Waterfront Home Available
Winneconne, WI
13% off
Price is NZ$9,737
NZ$9,737
NZ$1,391 per night
includes taxes & fees
Image gallery for River Front Cottage/Private Dock-Walk to Bar/Restaurants
9.49.4 out of 10 rating
Exceptional
(28 reviews)
River Front Cottage/Private Dock-Walk to Bar/Restaurants
Fremont, WI
7% off
Price is NZ$2,496
NZ$2,496
NZ$357 per night
includes taxes & fees
Image gallery for 4 bedroom Water Front Home!! NFL DRAFT!! EAA, FISHING, BOATING!!
1010 out of 10 rating
Exceptional
(5 reviews)
4 bedroom Water Front Home!! NFL DRAFT!! EAA, FISHING, BOATING!!
Oshkosh, WI
8% off
Price is NZ$7,164
NZ$7,164
NZ$1,023 per night
includes taxes & fees
Image gallery for Come Enjoy the Our Lakeside Getaway!
1010 out of 10 rating
Exceptional
(11 reviews)
Come Enjoy the Our Lakeside Getaway!
Winneconne, WI
8% off
Price is NZ$3,558
NZ$3,558
NZ$508 per night
includes taxes & fees
Image gallery for Experience Oshkosh charm near EAA Aviation Museum
1010 out of 10 rating
Exceptional
(22 reviews)
Experience Oshkosh charm near EAA Aviation Museum
Oshkosh, WI
8% off
Price is NZ$2,771
NZ$2,771
NZ$396 per night
includes taxes & fees
Image gallery for Peaceful Home in Heart of Oshkosh!
1010 out of 10 rating
Exceptional
(14 reviews)
Peaceful Home in Heart of Oshkosh!
Oshkosh, WI
6% off
Price is NZ$2,066
NZ$2,066
NZ$295 per night
includes taxes & fees
Image gallery for Lovely Lake Winnebago beachfront home, EAA, Packers, water activities, skiing
1010 out of 10 rating
Exceptional
(86 reviews)
Lovely Lake Winnebago beachfront home, EAA, Packers, water activities, skiing
Neenah, WI
8% off
Price is NZ$6,592
NZ$6,592
NZ$942 per night
includes taxes & fees
Image gallery for Lake house with easy access to Fox Valley cities
1010 out of 10 rating
Exceptional
(35 reviews)
Lake house with easy access to Fox Valley cities
Larsen, WI
8% off
Price is NZ$4,747
NZ$4,747
NZ$678 per night
includes taxes & fees
Image gallery for Spacious home: Lake Winnebago, fishing, kayaking
1010 out of 10 rating
Exceptional
(6 reviews)
Spacious home: Lake Winnebago, fishing, kayaking
Fond du Lac, WI
8% off
Price is NZ$3,648
NZ$3,648
NZ$521 per night
includes taxes & fees
Image gallery for Retreat on Lake Winnebago
9.89.8 out of 10 rating
Exceptional
(118 reviews)
Retreat on Lake Winnebago
Oshkosh, WI
8% off
Price is NZ$3,779
NZ$3,779
NZ$540 per night
includes taxes & fees
Image gallery for Lake Winnebago Water Front! Fishing! Boating! Quiet Bay! EAA!
9.89.8 out of 10 rating
Exceptional
(44 reviews)
Lake Winnebago Water Front! Fishing! Boating! Quiet Bay! EAA!
Oshkosh, WI
8% off
Price is NZ$3,944
NZ$3,944
NZ$563 per night
includes taxes & fees
Image gallery for 3BR by Menominee Park • Firepit • Gazebo • Walk to Lake & Zoo
9.49.4 out of 10 rating
Exceptional
(9 reviews)
3BR by Menominee Park • Firepit • Gazebo • Walk to Lake & Zoo
Oshkosh, WI
19% off
Price is NZ$3,497
NZ$3,497
NZ$500 per night
includes taxes & fees
Image gallery for 2025 NFL Draft, Green Bay Packer home games and EAA rental on Lake Winnebago
1010 out of 10 rating
Exceptional
(5 reviews)
2025 NFL Draft, Green Bay Packer home games and EAA rental on Lake Winnebago
Menasha, WI
8% off
Price is NZ$5,445
NZ$5,445
NZ$778 per night
includes taxes & fees
Image gallery for Lola's Lakeside Estate on Lake Winnebago
1010 out of 10 rating
Exceptional
(13 reviews)
Lola's Lakeside Estate on Lake Winnebago
Hilbert, WI
9% off
Price is NZ$9,110
NZ$9,110
NZ$1,301 per night
includes taxes & fees
Image gallery for Lake, River and Lighthouse View Suite<br>
1010 out of 10 rating
Exceptional
(11 reviews)
Lake, River and Lighthouse View Suite<br>
Neenah, WI
7% off
Price is NZ$3,779
NZ$3,779
NZ$540 per night
includes taxes & fees
Image gallery for New Renovation! Gorgeous Lake Views! Outdoor Hot Tub, Huge open concept rooms!
1010 out of 10 rating
Exceptional
(6 reviews)
New Renovation! Gorgeous Lake Views! Outdoor Hot Tub, Huge open concept rooms!
Oshkosh, WI
8% off
Price is NZ$6,578
NZ$6,578
NZ$940 per night
includes taxes & fees
Image gallery for Hang out at The Hangar! Newly remodeled, beautiful home, fully furnished.
9.69.6 out of 10 rating
Exceptional
(42 reviews)
Hang out at The Hangar! Newly remodeled, beautiful home, fully furnished.
Oshkosh, WI
8% off
Price is NZ$6,994
NZ$6,994
NZ$999 per night
includes taxes & fees
Image gallery for Luxury In A Quaint Little Package
8.48.4 out of 10 rating
Very good
(5 reviews)
Luxury In A Quaint Little Package
Oshkosh, WI
12% off
Price is NZ$1,068
NZ$1,068
NZ$153 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Oshkosh
Secluded Lake House Retreat – Book Now!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
46 reviews(46 reviews)
3,500 sq/ft house with large outdoor space & a basement with bar/pool table.
Sleeps 12 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Home in Oshkosh near EAA Air Venture - 5 blocks away from Wittman Airport
Sleeps 10 · 2 bedrooms · 1 bathroom
Lola's Lakeside Estate on Lake Winnebago
Sleeps 7 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
House for Rent- EAA
Sleeps 5 · 2 bedrooms · 1 bathroom
Spacious Escape Near Supper Clubs, Trails, Lake Winnebago,& Family Fun parks!
Sleeps 9 · 6 bedrooms · 4+ bathrooms
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value