Your Home Away From Home

Your stay starts here. Choose TJ’s Destination Oshkosh. Beautiful vacation rentals in Oshkosh and surrounding areas. Stay. Relax. Repeat.

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Our Portfolio

Hickory on the Lake

4.97 (124)

Oshkosh, Wisconsin

3 bedrooms•3 baths

$852for 2 nights•Oct 30 – Nov 1

Goyke

4.94 (81)

Oshkosh, Wisconsin

3 bedrooms•3 baths

$853for 2 nights•Nov 9 – Nov 11

Hickory Hideaway

4.88 (88)

Oshkosh, Wisconsin

2 bedrooms•1 baths

$633for 2 nights•Dec 1 – Dec 3

Kalbus House

4.98 (115)

Oshkosh, Wisconsin

4 bedrooms•3 baths

$1,047for 2 nights•Oct 30 – Nov 1

The Harbor Hideaway

4.98 (167)

Oshkosh, Wisconsin

4 bedrooms•4 baths

$916for 2 nights•Dec 1 – Dec 3

Kalbus Cottage

4.80 (117)

Oshkosh, Wisconsin

2 bedrooms•1 baths

$342for 2 nights•Oct 29 – Oct 31

Lilly Lakeside

4.95 (130)

Oshkosh, Wisconsin

4 bedrooms•3 baths

$840for 2 nights•Dec 1 – Dec 3

Grandma's Cottage

5.00 (4)

Oshkosh, Wisconsin

3 bedrooms•1 baths

$431for 1 night•Oct 29 – Oct 30

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At TJ’s Destination Oshkosh, we offer elevated vacation rentals in Oshkosh and surrounding areas, thoughtfully designed for families, groups, corporate stays, and getaways of all kinds. Our professionally managed homes combine comfort, space, style, and premium amenities to make every stay feel effortless and inviting.

Our mission is simple: to provide high-end vacation rentals that bring people together. Whether you’re exploring Lake Winnebago, enjoying local events, or simply reconnecting with the people who matter most, we create spaces where you can relax, feel at home, and make lasting memories.

Choose TJ’s Destination Oshkosh for elevated lodging, personalized hospitality, and a stay worth remembering.

Featured Vacation Rentals

Goyke

Lakeside views, cozy spaces & 3 Bedroom, 3 Bath comfort. Relax by the firepit or walk to TJ's Harbor. Your getaway awaits!

Hickory On The Lake

Your stylish 3 Bedroom, 3 Bath waterfront escape with stunning Lake Winnebago views, sunrises, sunsets & year-round comfort.

Highland Farmhouse

A refined farm retreat for up to 16 guests, blending elevated comfort, charming animals, fireside evenings & fresh eggs.

Warm Welcomes in Oshkosh, WI

More Than a Place to Stay

What our guests say

4.94

879 reviews

“Lovely large house, that was very clean and well maintained. It was perfectly placed on the lake. Would highly recommend for a large outing.”

Nicholas

Stayed in October 2026

“Romantic and fun Positive: The location is literally perfect and so private couldn’t have been better Negative: The water smells like mud”

Peter

Stayed in October 2026

“Very nice!”

JingJing

Stayed in October 2026

“The house was excellent. It was exactly as in the pictures. The house was clean, in great shape, and had a nice view of Lake Winnebago. It was easy to access the house and communications were prompt. We enjoyed being able to use the garage for our cars. The only minor problem was that the Keurig machine did not work. I would gladly stay there again.”

Jerry

Stayed in October 2026

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