Family-friendly vacation rentals in Elkhart Lake

Fernwood Elkhart Lakefront: hot tub, pier, kayaks

Beautiful, serene lakehome on pristine Elkhart Lake. The hot tub, deck, screen porch & stone patio all have gorgeous lake views. The private pier is perfect for a dip, paddling or lounging by the water before basking in a luxurious sunset soak in the hot tub. Enjoy a stroll into the adorable town of Elkhart via the rustic lakefront path. With a chef’s kitchen and extensive amenities, it's perfect for a weekend or extended stay year round! We strive to be inclusive and welcoming 🏳️‍⚧️BLM🏳️‍🌈

Kitchen · Family · Checkout

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

Indoor spaces · Kitchen · Beach

The LODGE in Elkhart Lake. —-Hot Tub & Arcade—-

Rustic modern home w/ hot tub, arcade & fireplace right on the edge of Elkhart Lake. Road America, great golf, The Ice Age Trail, & the Kettle Moraine are all at your doorstep. This cozy home is 4 blocks from the downtown of Elkhart lake. Yet it still has an acre to explore & enjoy nature. Only 4 miles from Road America. 2 bedroom w/ 2 extra sofa sleepers & 2 baths. Perfect for racers or romantic getaways. The arcade/Pinball room has over 10 games. Perfect base camp. We got your bases covered

Indoor spaces · Family · Backyard

The 2400 sq ft Plymouth Paddock near Road America!

This charming two story, 2400 square ft colonial house is the perfect respite for families looking to connect, or race fans looking for a home during race weekend. Only 4 miles from Road America the location is close to all of Sheboygan County's finest attractions. Located two blocks from downtown on a quiet street, its up to you how you want to spend your evening. You could walk downtown for a bite, have a campfire, make a meal, or just spend time together. Welcome to your home away from home!

Indoor spaces · Family · Outdoor spaces

Stay in a Real Castle on a Vineyard

Stay at one of the most Wishlisted Airbnbs in the world — a castle on a vineyard. Featured in Men’s Journal and on the cover of Haven magazine, The Castle Vineyard is a 20-acre estate built for unforgettable stays. 🍇 Vineyard estate with spa, sauna & wildlife views 🎬 Theater, arcade, PS5 & golf simulator 🍽️ Chef’s kitchen with Viking appliances 🔥 Fire pit, patio & hot tub 🏰 “Felt like royalty… every detail was magical.” 🎉 Entire estate is yours. Ask about our exclusive Tasting Room.

Family · Indoor spaces · Checkout

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

Kitchen · Family · Layout

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!

Family · Kitchen · Nearby

hot tub and sauna on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Kitchen · Indoor spaces · Check-in

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Kitchen · Family · Hiking

Lake House-Kayaks/Paddle Boards/Private Pier

🛶 Private Pier + Kayaks, Paddle Boards, & Lily Pad Raft 🏖️ Direct Lake Access with Crystal Clear Water ✨ Fully Renovated (2025) 🛏️ 4 Bedrooms with Premium Mattresses & Hotel-Quality Linens 🚿 2.5 Modern Bathrooms + Laundry Room 🍳 Chef-Friendly Kitchen with High-End Appliances ❄️ Central A/C, Fast WiFi, and Ample Parking 🏁 5 Mins to Road America | 20 Mins to Kohler Golf & Spa 🧭 Under 1 Hour to Milwaukee & Green Bay Attractions 🛟 Life Jackets & Water Toys Provided

Indoor spaces · Family · Checkout

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!

Indoor spaces · Family · Pool

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.

Family · Indoor spaces · Comfort