Apartment holiday rentals in Oshkosh

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!

Historic&Modern Kiel 4B near Elkhart Lake & Kohler

Your family, friends or race team will stay in the heart of Kiel, WI. Fine dining, Yard 65 Brewery and restaurants all within walking distance in beautiful & safe downtown Kiel. 10 minutes to the main gate of historic Road America in Elkhart Lake & under 1 hour to Milwaukee and Green Bay. Within minutes of Wisconsin supper clubs like the Fork & Dagger or Schwartz's. Perfect fit for families or larger groups coming from all over and want to stay together or 2 couples wanting some privacy!

Janelle's Dockside Condo

GREAT LOCATION!! Built in late 2020. Come visit our luxury, "Nautical Themed" 2 bedroom condo in Sheboygan, WI located on the confluence of Lake Michigan and the Sheboygan River in the charming South Pier District. Relax on the deck with a beverage and watch the sailboats pass by. Stroll the boardwalk for fine dining, charter fishing, quaint boutiques or an afternoon ice cream. World class golfing at Black Wolf Run or Whistling Straights. Equipped with everything you need and more!

The Lake Street Kickback in Elkhart Lake!

Welcome to The Lake Street Kickback! This privately owned studio condo is located at The Shore Club of Wisconsin & has access to all resort amenities. During your stay enjoy the outdoor pool/hot tub, resort beach, Tiki bar, on site restaurant, indoor pool & game room. 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.

Lambeau Loungin' in Green Bay (Upper Home)

Sure to please with $0 cleaning fees! LOCATION! LOCATION! LOCATION! Upper unit of a licensed duplex property (**pricing is for upper unit only**) 1 mile from Lambeau Field, Resch Center - Resch Expo and surrounding venues. All the amenities to complete your stay for occasions like Packer games, concerts or just exploring Green Bay and northeast Wisconsin! Footsteps from one-of-a-kind local food and convenience options. Dogs welcome (pet rules and one-time pet fee apply).

Beachside Lake View - 2br - First Floor - Garage

Located just one lot in from the beautiful shores or Lake Michigan. Amazing location provides year round stunning views . This is a lower 2 bedroom 1 bath condo in a 4unit building were all the units have the same basic layout. You can listen to the waves or walk just a few feet and have the sand on your feet. This condo features front and rear balconies. Makes for a great place to enjoy a weekend get away or a place to relax at night while on a business trip.

Sheboygan Sunrise Beach Stay

*** STEPS AWAY FROM LAKE MICHIGAN*** Experience the vibrant energy from our stylish apartment with great views. Enjoy easy access to the beach, restaurants, bars and a cozy stylish getaway for unforgettable relaxation and adventure. The apartment features fully equipped kitchen, cozy living area, and comfortable bedrooms. You are in the center of it all, walking distance to Lake Michigan and the Beach, Bars, Restaurants, River Boardwalk, and Historical Downtown.

East Side Reside - Sleeps Five!

20 minutes to EAA, and 30 minutes to Elkhart, this spacious townhome offers TWO Queen-Sized bedrooms and a full-sized sofa to sleep (5) comfortably, a desk to work at, two bathrooms, and a fully stocked kitchen to prepare anything you need! Enjoy 500 Mbps fiber internet as well to work from home! *TOP ATTRACTIONS NEAR US* - Elkhart Lake (17 mi) - EAA (20 mi) - Road America (16 mi) - Whistling Straits (26 mi) - Lake Winnebago (2.1 mi) - Lake Michigan (37 mi)

Car Condo Rental in Elkhart Lake

New construction luxury condo in Elkhart Lake. Located in the Wolf Luxury Motor Courts complex. Spacious 2 bedroom 2 full bath condo with balcony. Open concept kitchen and living area with large island/eating space. Located 20 minutes from Whistling Straits golf course. Enjoy legendary Elkhart Lake, home to award winning restaurants, historic downtown, and gorgeous lake views from local night spots. Condo is 1/2 mile north of Road America race track.

Lighthouse Lookout - 3BR | Steps to Lake Michigan

Lighthouse Lookout by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. Discover the ultimate retreat at Sheboygan's Riverfront condo with stunning river and Lake Michigan views. This top-floor 3BR/2BA unit features a master jacuzzi tub and over 1,600 sq ft of space. Enjoy riverside dining, fishing charters, nearby shops, restaurants, and championship golf at Kohler properties.

Bright home w/ private beach & lake access

Hello and welcome to your peaceful Elkhart Lake escape, where lake views, historic character, and cozy comforts come together for a relaxing stay. - Sleeps 2 | 1 bedroom | 1 bed | 1 bath - Lake & beach views w/ waterfront & lake access - Seasonal pool access (outdoor amenities Memorial Day–Labor Day) - Covered patio for fresh-air moments - Kitchen & bathroom essentials included - Private entrance in a standalone condo

Quiet condo w/ decks & beach access

Hello and settle into a relaxing lakeside stay just steps from Lake Michigan. This main-level condo pairs comfort, views, and an unbeatable location for a peaceful coastal escape. - Sleeps 4 | 2 bedrooms | 2 beds | 1 bath - Dual decks w/ lake views - Waterfront location w/ shared beach access - Electric fireplace for cozy evenings - Kitchen, in-unit laundry & dedicated workspace - Beach essentials & free parking