Hotels in Sheboygan County

New luxury hotel in the heart of downtown Plymouth

A fully renovated luxury hotel in the heart of downtown Plymouth, thoughtfully updated in 2025-2026 to offer refined comfort, short or longer term stays, a modern design, and upscale studios, 1 BR and 2 BR units, just minutes from Road America and perfectly situated for exploring the city’s shops, dining, and waterfront charm. Each suite features either full kitchens, or kitchenettes. Outdoor grill, picnic table, and lobby office station, coffee, and lounge seating. Steps from restaurants-bars.

Bea's Beachside Condo Rental

Nestled in the heart of picturesque Elkhart Lake, (just 2 miles from Road America), this is the perfect place to unwind and explore. This privately owned studio condo is located at the Elkhart Lake Beach Resort (formerly The Shore Club of WI) and includes access to all resort amenities. During your stay, you can enjoy the outdoor pool and hot tub, resort beach, Tiki bar, and indoor pool. You’ll also be just steps away from local restaurants, bars, shops, and the seasonal Farmers Market.

Three Bedroom Two Bath Condo

This spacious condo includes three separate bedrooms. The master bedroom has one queen bed, an ensuite bathroom, and access to the covered veranda. The second and third bedrooms each have one queen bed. The second bath is in the common area. Unit has an open-concept floor plan with a living room (sofa sleeper & gas fireplace), fully equipped kitchen, dining area, and a covered veranda. Limited on-site parking. Street parking is available. No smoking in the unit.

Historic Adjoining Hotel Rooms

Two hotel rooms adjoined by a Jack & Jill bathroom. Each room has two double beds, a sink, and a closet. Each Room is approximately 175 square feet. Includes complimentary Wi-Fi and a 42" LCD TV with cable television. The room is located in a historic building accessible only by stairs. Approximately 12 steps to the first level and an additional 14 steps to the second level. Limited on-site parking. Street parking is available. No smoking in the unit.

Historic Hotel 1 Double & 1 Twin

Petite, European-style hotel room with one double bed, one twin bed, and a private bathroom. The room is approximately 160 square feet. Includes complimentary Wi-Fi and a 42" LCD TV with cable television. The room is located in a historic building accessible only by stairs. Approximately 12 steps to the first level and an additional 14 steps to the second level. Limited on-site parking. Street parking is available. No smoking in the unit.

Historic Hotel Two Double Beds

Petite, European-style hotel room with two double beds and a private bathroom. Approximately 175 square feet. Includes complimentary Wi-Fi and a 42" LCD TV with cable television. The room is located in a historic building accessible only by stairs. Approximately 12 steps to the first level and an additional 14 steps to the second level. Limited on-site parking. Street parking is available. No smoking in the unit.

Hidden Gem with a Lake View in heart of Elkhart

Sweet & Simple Boutique Hotel room with shady lake views, just steps from historic Elkhart Lake. I includes semi-private deck overlooking the lake. The space features one large bathroom (shower/tub), classic Kohler fixtures, and plenty of towels and toiletries. NEW Sealy Queen mattress. Room also includes a small fridge, Keurig coffee maker, and a selection of breakfast bars. 1 Parking spot in private lot included

Historic Hotel One King Bed

Our Historic Hotel Rooms comprise the Elm Park Hotel, and the Lake Cottage, where guests are offered comfortably simple accommodations in the heart of Elkhart Lake, Wis. Keep in mind when booking, our Historic Hotel Rooms weren’t constructed with an elevator so guests should be prepared to walk one, sometimes two flights of stairs, along with first come, first serve parking and A/C. No smoking in the unit.

The Osthoff Resort & Spa 2 Bedroom Lakeview

Looking for the perfect lakeside escape? The Osthoff Resort & Spa, a beautiful AAA Four Diamond retreat nestled along the shores of Elkhart Lake, WI, has you covered. Whether you're planning a family adventure by the water, a peaceful spa weekend, or simply craving some time to unwind and take in the natural beauty of the lake, this is where your getaway begins.

Two Bedroom Condo One Full Bath

This spacious condo has two separate bedrooms, each with one queen bed. The one bathroom is located in the condo's common area. Unit has an open-concept floor plan with a living room (sofa sleeper & gas fireplace), fully equipped kitchen, dining area, and a covered veranda. Limited on-site parking. Street parking is available. No smoking in the unit.

Room 3 at Christi's Inn located right off town sq.

This room has one queen bed. A modern approach to a Victorian Inn. The front porch is great fun for gathering and right off the town square and only one block from the lake. Located a few houses up/in between The Osthoff and Siebkens Resort. Please note: We will consider a one night reservation on some quieter weekends. Just ask!!!

Balcony Hotel One Queen Bed

This spacious hotel room, located in our condominium building, has one queen bed, a private bath, and a covered veranda. Rooms range between approximately 255 - 275 square feet. Includes complimentary Wi-Fi and cable television. Limited on-site parking. Street parking is available. No smoking unit.