Holiday 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

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.

Comfortable two bedroom stay, close to EAA.

Your family will be close to everything when you stay at this centrally-located place. We are 2.3 miles away from EAA, 1.4 miles away from Walmart and 4 miles away from downtown. Our home offers two bedrooms equipped with two queen size beds, along with a queen size air mattress for the large living room area. We also have a very family friendly basement with a pullout couch and a fenced in spacious back yard with a trampoline and swimming pool. Please consider allergies as we have two cats.

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.

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.

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.

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!