Holiday rentals with a pool in Elkhart Lake

4 br 4.5 acre secluded country property

Secluded country property 4 minutes from FDL, 20 minutes to EAA, 40 minutes to Road America, 60 minutes to Milwaukee or Green Bay. Very private set back 505 ft from road. Lots to do outside w/ pond, pool, large deck, woods w/ walking trails, large yard, amazing bunk house w/ loft & 2 bunk beds. Inside the 2300 sq ft home all of the rooms are well sized. Plenty of room to spread out for a large family or group. Enjoy 2 living rooms and a movie theater room in the basement w/ 110 inch screen.

Lakefront Condo, Private Beach/Pools, Walk to Town

Elkhart Lake’s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, pools (indoor/outdoor), hot tub, water sports rentals, and easy access to 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!

Resort Life 2 Queen Suite

WELCOME RACE FANS AND VACATIONERS!!!! The Victorian Inn is located along a picturesque freshwater lake and within walking distance to exciting events and adventures!Our rooms offer easy access to an indoor pool, outdoor pool, fresh water lake, and so much more! Victorian Inn is situated in the heart of downtown Elkhart Lake near several specialty shops and restaurants. We're also just 2 miles from Road America, 8 miles from Kettle Moraine State Forest, and a short drive to PGA golf courses!

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.

Resort Condo on Elkhart Lake

Enjoy Lake life on Elkhart Lake in our resort condo steps to beach, in and outdoor pool. 2 miles to Road America, 2 minutes walk to the clear waters of Elkhart Lake, multiple options for dining, cocktails, and coffee: The Tiki bar with live music, and the famous "Off The Rails" for a perfect coffee beverage. Our home features: 2 bedrm ensuite with extra 1/2 bath, Living rm with fireplace, huge windows and lake views. Deck with lake views and Kitchen with everything you might 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.

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.

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

Magical Retreat in Elkhart Lake on 4 private acres

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!

Road America lake house.

Road America adjacent lake house. Great location, two minutes to the track. Towns of Elkhart Lake, Plymouth and Kohler are minutes away. Whistling Straits golf course is twenty minutes down the road. Four bedroom house with full kitchen and laundry room. House features an indoor pool, gazebo on the deck overlooking the lake. Three kayaks and a row boat down lakeside. Ping pong table inside on the pool level.

Breezy Acre...Relaxing small family get a way.

Close to home get away. Awesome 21 foot camper that sleeps 2 adults, 1 child OR 3 adults. Kitchen, shower, refrigerator with freezer, stove with oven, electric, water, in backyard of country home in Campbellsport, WI. Use of hot tub, pool(weather permitting...usually up and running by June 15th) and outside grill available. Come enjoy your stay at Breezy Acre....