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.

EAA Ready Spacious Home 7/19 - 7/26

Located on the southeast side of Neenah. 20 min/16.5 miles from the EAA Air Venture grounds. Come and rest after a long day at EAA. This spacious 4/5 bedroom (1 Queen, 3 fulls, 1 futon and 1 twin. 2 queen air mattresses available), 3.5 bath has plenty of room for everyone. Enjoy a dip in the private pool or watch the kids from the patio. The patio has a cozy seating area as well as a dining area. Feel free to grill out. There is a fire pit if you want to hang out and roast some marshmallows.

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!

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.

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.

Peaceful 4BR Country Escape

Escape to wide-open spaces and quiet country charm in this spacious 4-bedroom, 2.5-bath home set on several scenic acres. Comfortably sleeping 7 guests, this inviting retreat is perfect for families or small groups. Conveniently located just 21 miles from the EAA, this home provides easy access to the excitement of the event while offering a quiet, private place to recharge at the end of the day.

13 Miles to EAA AirVenture | Sleeps 14 | Pool

Make our spacious home your EAA AirVenture headquarters! Located just 13 miles from the grounds, our home sleeps up to 14 guests and features a private pool, fully equipped kitchen, and plenty of room to relax after a day of aviation excitement. Skip the crowds and enjoy the comfort, privacy, and convenience of a home that’s perfect for pilot groups, exhibitors, families, and aviation enthusiasts.

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.

Newly Renovated -Oshkosh Home on Lake Winnebago

✨ Hickory on the Lake – Your Lake Winnebago Vacation Rental in Oshkosh! 🌊🏡 🛏️ 3 Bedrooms | 3 Bathrooms – A stylish and comfortable Oshkosh vacation rental, perfect for couples, families, or a relaxing Lake Winnebago getaway. ☀️ Four-Seasons Room – Enjoy morning coffee or evening drinks while taking in breathtaking Lake Winnebago sunrises and sunsets.

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!