Holiday 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.

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.

Riverfront Appleton Home with Pool & Boat Dock!

Situated along the banks of the Fox River lies this 3-bed, 2.5-bath Appleton vacation rental! Boasting a fully equipped kitchen, a pool, and a private boat dock, this home has it all. Spend your days splashing around in the pool, grilling out on the patio, or fishing from the dock. End the night cozied up by the fire pit, watching the sunset and roasting marshmallows. Whether it’s an exciting adventure or a peaceful escape you seek, this retreat is the perfect place for your next getaway!

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.

Perfect Oasis for EAA guests

Forget your worries in this spacious and serene space. Enjoy the feeling of home while on vacation. Relax in the pool, have a drink on the deck or patio, grill out or just rest in the air conditioning. This pristine clean home will provide you all the amenities that you need to enjoy your vacation and not be far from activities to do in the area. 15 minutes from the EAA grounds, 10 minutes from Oshkosh, 25 minutes from Appleton, 45 minutes from Green Bay.

Resort in the city

1920's character home on Doty Island perfect for relaxation or home base to explore the Fox Cities. Private backyard, inground heated pool along with 23 acre Smith Park out your front door make this an easy choice to find something that suits everyone's wants. Enjoy a walk or bike-ride around the quiet neighborhoods or link to the many bike trails accessible out the front door. Enjoy dinner on the front porch while watching the sunset.

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.

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!

Hickory Hideaway- 2 Bedroom with Lake views

Escape to our charming two-bedroom cottage on Lake Winnebago, where tranquil lake views invite relaxation. With 2 bedrooms and 1 bath, it's the perfect setting for a peaceful retreat. Nestled in a quiet, family-friendly neighborhood, our cottage is your ideal hub for exploring Oshkosh's delights. Your lakeside escape awaits!

10 Miles from EAA

After a full day of activities relax by the firepit or take a dip in the above ground pool. This property is situated on almost an acre in the City of Omro which is only a 15 minute drive to the EAA grounds in Oshkosh, WI. This property is 2 blocks from the Fox River and 2 blocks from a wonderful walking path.

The Schmidt Haven

Relax with the whole family at this peaceful place to stay. Take a dip in the pool before EAA, or after a hot day at the EAA grounds. Extra room in the basement. Watch the birds, sometimes ducks or deer out the patio window.