Your Stay Comes with the Keys to Oshkosh
When you book with TJ's Destination Oshkosh, you don't just get a place to sleep — you get VIP access to some of the best dining, drinks, and poolside
One Family. Four Legendary Spots. All Yours.
TJ's Destination Oshkosh is more than vacation rentals. It's a local hospitality family that's been shaping the Oshkosh experience for years. From sizzling steaks to lakeside cocktails to a dip in a country club pool, our guests get exclusive perks at every stop along the way. Think of it as your personal tour of the best Oshkosh has to offer, with the red carpet already rolled out.
Stop One: TJ's Highland Steakhouse
A refined dining experience right here in Oshkosh. TJ's Highland Steakhouse serves hand-cut steaks, fresh seafood, and scratch-made dishes in a warm, upscale atmosphere. From their signature prime rib to seasonal specials, this is where locals celebrate and visitors become regulars. Guests of TJ's Destination Oshkosh enjoy special dining perks when they reserve.
Hand-Cut Steaks & Prime Rib
Every cut is hand-selected and prepared to order. Their prime rib is legendary in Oshkosh — arrive early, because it sells out.
Full Bar & Wine List
Craft cocktails, local brews, and a curated wine list that pairs perfectly with every entrée on the menu.
Guest Perk
Stay with TJ's Destination Oshkosh and enjoy exclusive perks at the steakhouse during your visit. Ask us for details when you book.
Hand-Cut Steaks & Prime Rib
Every cut is hand-selected and prepared to order. Their prime rib is legendary in Oshkosh — arrive early, because it sells out.
Full Bar & Wine List
Craft cocktails, local brews, and a curated wine list that pairs perfectly with every entrée on the menu.
Guest Perk
Stay with TJ's Destination Oshkosh and enjoy exclusive perks at the steakhouse during your visit. Ask us for details when you book.
Stop Two: TJ's Harbor Restaurant
Waterfront dining on the Fox River with stunning views, cold drinks, and a menu built for long summer nights. TJ's Harbor is the kind of place where a quick lunch turns into an all-afternoon affair, and nobody minds one bit.
What Makes TJ's Harbor a Must-Visit
Casual waterfront dining with serious flavor — right on the Fox River.
Dock your boat and walk right in
Outdoor patio with river views
Craft cocktails and local taps
Exclusive perks for our guests
Exclusive Guest Access
Stop Three: Oshkosh Country Club Pool
Here's something most vacation rentals can't offer: access to the Oshkosh Country Club pool. When you stay with TJ's Destination Oshkosh, you and your group can cool off at this beautiful private pool, no membership required. It's the perfect way to spend a lazy afternoon between adventures.
The Pool
A pristine semi-private pool reserved for members and our guests.
Poolside Relaxation
Lounge chairs, sunshine, and zero stress.
Family Friendly
Plenty of room for kids and adults alike to enjoy the water.
Stop Four: Ardy & Ed's Drive-In
No trip to Oshkosh is complete without a stop at Ardy & Ed's, a genuine 1950s-style drive-in restaurant that's been serving burgers, root beer floats, and nostalgia since the carhops first started rolling. Pull up, flash your lights, and let them bring dinner to your window. It's an Oshkosh institution.
Classic Drive-In Experience
Carhops on roller skates, neon lights, and food served right to your car window. It's like stepping back in time — in the best way.
Burgers, Shakes & Root Beer Floats
The menu is exactly what you're hoping for: juicy burgers, hand-dipped shakes, onion rings, and their famous root beer floats.
An Oshkosh Tradition
Ardy & Ed's has been a beloved local landmark for decades. If you're visiting Oshkosh, this is non-negotiable.
Classic Drive-In Experience
Carhops on roller skates, neon lights, and food served right to your car window. It's like stepping back in time — in the best way.
Burgers, Shakes & Root Beer Floats
The menu is exactly what you're hoping for: juicy burgers, hand-dipped shakes, onion rings, and their famous root beer floats.
An Oshkosh Tradition
Ardy & Ed's has been a beloved local landmark for decades. If you're visiting Oshkosh, this is non-negotiable.
Guests Love the Full Oshkosh Experience
We had no idea the rental came with perks at the steakhouse and harbor restaurant. It made our trip feel so special — like we were locals, not tourists.
Rachel K.
The kids loved Ardy & Ed's and the country club pool. We loved the steakhouse date night. Everyone won.
Mike & Jen D.
TJ's Harbor on the river was the highlight of our weekend. Great food, great views, and our host set us up perfectly.
Tom S.
Book Your Stay. Unlock the Whole Experience.
Steaks, sunsets on the river, poolside afternoons, and root beer floats. It all comes with your reservation at TJ's Destination Oshkosh.