Vacation rentals with a pool in Winnebago County

Great EAA Location by the Airport

Three bedroom (5 beds), 2 full bathroom home available for for rent the week of EAA. Located only a couple minutes from the EAA grounds, vendor entrance, HWY 41, & Seaplane Base. Enjoy amenities like a swimming pool, large deck, gas grill, in a country setting where you can still see some of the airshow after a long day! Also a fire table on the deck, trampoline in the backyard, and a bar area on the lower level... free to use it all at your own risk of course 😜 The home is yours for your stay

Value · Family · Pool

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.

Location · Family · Hot tub

Trendy, spacious home for rent

Built in 2013, our updated home is conveniently located just off Highways 41 and 10 in Neenah—only 20 minutes from EAA. Originally built as a spec home, we've transformed the space with thoughtful updates, including a stunning sun room that's perfect for relaxing year-round. Our home has five bedrooms and three bathrooms, a fully equipped kitchen, a welcoming living room, dining area, office/den, laundry room, mudroom, playroom, and a cozy outdoor space to unwind after a day in the Valley!

Family · Location · Pool

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, small family gatherings, and group getaways. With 3 spacious bedrooms, 7 beds, 3 full bathrooms, and an open-concept layout, there’s room for everyone to relax. Whether you're prepping for a big day or enjoying a weekend retreat, this home has everything you need.

Location · Family · Layout

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.

Location · Family · Accuracy

Moore's Family Camper

We are located between Milwaukee & Green Bay in a very quiet subdivision. Camper stays on our property for your use. Camper has water, electric & propane hooked up. Some of our "extra special features" are: * Camper has a private Bunkhouse feature with a separate bedroom that has 3 of the beds or 2 beds and one additional table * Paved bike trail accessible from our subdivision * WiFi Connection

Comfort · Cleanliness

EAA Adventure

Relax at this peaceful place to stay. Clean spacious home. Large fenced in yard. Safe quiet location. Relax by the gas fire pit while grilling on the patio. Pool to enjoy on the hot summer evenings. Right down the road from the outlet mall and EAA grounds. Flyover planes. Gas grill and blackstone. Regular solo smokeless fire pit and gas fire pit. Crib, playpen, and multiple infant items available.

Poolside Retreat - EAA Rental

Quiet neighborhood only 20 minutes to AirVenture Oshkosh. Spacious single family home with fenced in backyard, in-ground pool, fire pit with gas/wood provided, grill, patio & screen porch. Perfect for large groups or families with two living spaces and kids' playroom in basement. Close to downtown Neenah. Located within a mile of a grocery stores, gas stations, restaurants, breweries/bars, etc.

Location · Amenities · Hospitality

Home with pool - close to Oshkosh

3 bedrooms, large family room with TV & couch, pool table and bar area (pull out couch also available), outdoor sitting area with gated heated pool (ask for this amenity prior to arrival) one acre lot with space for outdoor activities. Outdoor fire-pit and chairs/wood available for use. Hammocks put up in the summertime and plenty of parking space in the driveway and the back driveway as well.

Check-in · Checkout · Hospitality

Top guest favorite

Guest favorite

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!

Family · Location · Nearby

Goyke House- Best sunrises and sunsets

🏞️ Welcome to Goyke – Lakeside Luxury Awaits! ✨ Relax in Style: Enjoy stunning lake views paired with modern comfort. 🛋️ Unwind with Ease: Thoughtfully designed spaces make every moment at home feel effortless. 📅 Plan Your Escape: Book today and experience the perfect mix of style, comfort, and lakeside serenity!

Location · Value · Cleanliness

Lake Winnebago Private Dock Indoor Pool Sleeps 22

Enjoy this spacious 6 bedroom, 5.5 bathroom home with an indoor pool and sauna on lake Winnebago in Oshkosh, Wisconsin. Accommodates up to 22 guests and has plenty of space to spread out with two large indoor living spaces.