Vacation rentals with a pool in Winnebago County

Riverfront Oasis w/ hot tub and seasonal pool

Riverfront home on Doty Island in peaceful residential area. Built in 1936, our home has character + charm. Seasonal heated pool, hot-tub & waterfront patio. Relax, kayak or fish off of the riverfront dock. 100 feet of Fox River frontage - minutes from Lake Winnebago by boat or kayak and 8 min to the highway. Come for some R&R or for an event (EAA) our family home is in the heart of it all! 5 bedrooms, 3 bathrooms. Hens providing fresh eggs daily! Licensed by the Menasha Health Department.

3 bedrooms, 5 miles to EAA & 45 miles to Green Bay

Home features 3 bedrooms, finished basement with pull out couch, 4 full baths, up to date kitchen , pool & raised brick patio with fire pit & gas grill. House is located less than 5 minutes from EAA grounds. Easy access to Hwy 41 for shopping & restaurants. This home is ideal for EAA vendors who after a long day are looking to come back to a peaceful place to relax but also gives the amenities of home for a family on vacation. This secluded place has everything you need for a peaceful stay.

Barndominium on Flower Farm | Pool + Vanity Space

Welcome to your dream stay in Oshkosh! Nestled on a working flower farm, this beautifully designed Magnolia Farms style barndominium offers the perfect blend of charm, comfort, and convenience—tailor-made for wedding parties, family gatherings, and group getaways. With 3 spacious bedrooms, 5 beds, 3 full bathrooms, and an open-concept layout, there’s room for everyone to relax and unwind. Whether you're prepping for a big day or enjoying a weekend retreat, this home has everything you need.

5 BR Oshkosh Home: 7 ml to EAA/1 ml to Hwy 41

Our home is big enough to host a large number of guests and also less than a mile to interstate 41, putting you at a quick 10 minute trip across town to the EAA, or less than a mile from Sunnyview Expo Center. We offer parking for several vehicles with an extra wide parking lot, as well as reservation dates prior to events if needed. We live in the northern township of Oshkosh, and are comfortably set just a bit in the country for privacy, yet close to town and all it has to offer.

Unique Luxury Stay (Firman)

Meticulously crafted and elegantly designed, The Wit Apartments for rent in Oshkosh, WI offer a wide array of luxury furnished apartments that seamlessly weave comfort, style, and functionality together to create the best living experience. Between the sophisticated apartment finishing touches and the top-of-the-line amenities – resort-style pool, bowling alley, and billiards room included; you’ll be falling head over heels in love with your stay at The Wit!

Hickory on the LakeWaterfront Luxury on Winnebago

Welcome to "Hickory on the Lake," a meticulously renovated 3-bedroom, 3-bath sanctuary on Lake Winnebago. Indulge in the beauty of stunning sunrises and sunsets from the four seasons room. Nestled in a quiet, family-oriented neighborhood, this centrally located property provides easy access to Oshkosh's attractions. Immerse yourself in sophistication and create unforgettable moments against the backdrop of Lake Winnebago's breathtaking scenery.

Beautiful, Large Home Close to EAA

This large 4 bedroom, 2.5 bath open concept home is clean, offers garage space, and has quick access to EAA. This well maintained home offers a large eat in kitchen, 1st floor laundry, over half acre lot, as well as a pool and hot tub to relax after the event. We provide new clean sheets, and blow up mattresses if needed, along with all towels and washcloths.

Home Away From Home

Family friendly neighborhood near downtown. 2 large bedrooms 1 w/ California king bed, futon, tv. 1 bedroom w/queen, tv. A large living room w/ plenty of room for all guests, dining room, & kitchen.There is a fenced in back yard w/ a pool, deck, fire pit, and grills. We live here, and are not professional cleaners, but try and make your stay as best as we can!

Old Schoolhouse Stay

Bring the whole family for a unique stay at an OLD SCHOOLHOUSE! Fun space with room for all! Perfect for large family gatherings. Peaceful setting with pool and hot tub. Mountain biking and hiking a short walk away. Snowmobiling & biking trails nearby and fishing minutes away. Kayaks and Canoes are available at request for your enjoyment!