Holiday rentals with a pool in Lake Winnebago

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.

VicVill | Historic Charm Meets Lakeside Comfort

The views though! Welcome to VicVill, our 2BR/2BA condo at Elkhart Lake Beach Resort <formerly Victorian Village> Enjoy stunning lake and pool views+a plush King master+matching twin-over-full bunks. Relax at the private resort beach, seasonal indoor/outdoor pools, + the Tiki Bar. Walk to village shops, restaurants, and water sports rentals. Perfect for track fans (5 mins to Road America), golfers (20 mins to Whistling Straits), and hikers. Settle in, check out, and enjoy your time away!

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.

Lakefront Condo, Private Beach/Pool, Walk to Town

Elkhart Lake’s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, private outdoor pool, hot tub, water sports rentals, Tiki Bar and nearby Osthoff Lake Deck, hiking, golfing, and town. Fall brings vibrant foliage, trail hiking, and golf on scenic courses. Winter offers cross-country skiing, snowshoeing, ice skating, sledding and trail hiking, while spring delights with blooming wildflowers, birdwatching, and farmers markets. Experience nature’s magic any season!

The Lake Street Kickback in Elkhart Lake!

Welcome to The Lake Street Kickback! This privately owned studio condo is located at The Elkhart Lake Beach Resort (Formerly The Shore Club of Wisconsin) & has access to all resort amenities. During your stay enjoy the outdoor pool/hot tub, resort beach and Tiki bar. A unique blend of updates, convenience, comfort & relaxation. Just steps away from local favorites including village restaurants, bars, farmers market, shops & neighboring resorts like Osthoff and Siebkens Resorts.

Road America Retreat-4 BDRM-2BA-Hot Tub+Pool

Private Craftsman home in Plymouth, WI—just 4 miles from Road America. Ideal for race teams and families, this two-story home offers 4 BDRMS, 2 BA, a private outdoor hot tub, and a seasonal heated inground pool (June-Sep). Free on-street parking plus a garage and shared driveway provide convenient vehicle access. Located in a quiet neighborhood near grocery stores, dining, and local attractions. No pets. Summers, Holidays, & RA race weekends require 3 night min.

A Sweet Suite in Freedom! Country Comfort!

Visiting friends or family in Freedom? Why bother them for an air mattress when you can stay right in town!? Going to a Packer Game and looking for a comfy place to stay with a super short drive? Found it! Ask about using the game room, golf simulator, or pool while you're here too! There's not a FULL kitchen!! Just one burner, and a flat griddle. There's also a microwave and small refrigerator/freezer, but overall, it's a suite. We think you'll LOVE it!

Private Beach, Pools & Full-Kitchen

🌊 Million-Dollar Views of Elkhart Lake from Covered Patio 🏊‍♂️ Outdoor Pools 🌿 Expansive Green Spaces 🚤 Private Beach & Lake Access 🍳 Full Kitchen w/High-End Gas Stove 🛁 Spacious Bathroom w/ Walk-In Tiled Shower 🛌 Charming Bedroom w/ Classic Touches & Historic Character 🏖️ Access to Private Shore Club Beach on Elkhart Lake 🕰️ Historic Touch: Part of the Old Schwartz Hotel + Prohibition-Era FBI Lookout Tower 📍 Unique, Standalone Condo

Secluded Elkhart Retreat | Pool, Hot Tub & Sunset

Nestled just minutes from Downtown Elkhart Lake, this custom-built cordwood home offers a secluded sanctuary experience. Perched atop a hill, the unique 16-sided house provides breathtaking views of the state forest and surrounding farmland. Despite its remote feel, you’re only a 5-minute drive from the charming Elkhart Lake business district. Day hikes on the ice age trail are just steps away from the home. Tap the ❤️ to save this listing!

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.

Lake Views | Walk Everywhere | 3BR Beach Resort

Stay Together at Elkhart Lake Beach Resort | 3BR Lakeview Condo for Couples & Friends Skip the split hotel rooms—this rare 3-bedroom, 3-bath condo at the Elkhart Lake Beach Resort is designed for groups who want to actually spend time together. Perfect for 2–3 couples or a small group of friends, you’ll have a true shared living space plus full access to one of Elkhart Lake’s most social, walkable resort experiences.