Holiday rentals with lake access in Sheboygan

4.91 out of 5 average rating, 344 reviews

Guesthouse in Oostburg

Beach House

This guesthouse is detached from the main house, comes with garage parking and has all the amenities you need including a wood-burning fire place! Towels, bath tissue, soaps & travel items. AC Window Unit. Kitchen includes pots/pans, dishes, mugs/glasses, coffee pot, toaster & microwave. Paper goods. New appliances/new water heater in 2020. Stairs to the apartment are on the northeast corner of the garage. The beach is steps away with a fire pit, boat house lounge, kayaks, beach toys & bicycles.

4.98 out of 5 average rating, 175 reviews

Apartment in Sheboygan

Modern Upstairs Apt - Steps from Lake Michigan

Have you ever wondered what Lake Life is like? Here is your chance! This is 1 of 2 AirBnB units in this cute duplex Come stay in this beautiful upper apartment located just one block from Lake Michigan. Take a quick walk to the lake in the morning to jump on your fishing boat or take the family to the beach in the afternoon! Located close to shopping and many local bars and restaurants within walking distance. You'll find relaxation and a great time here at the heart of Sheboygan's Shoreline!

4.97 out of 5 average rating, 122 reviews

Lakefront Charmer, cheerful decor gorgeous garden

This 2600 sqft lakefront home is a spacious retreat year round, friendly to kids and dogs. It is perched upon a bluff overlooking Lake Michigan with a gorgeous sunrise view. In winter, enjoy passing cargo ships and eagles along with ice formations. Inside, dine with seating and service for 12 after cooking in the spacious kitchen with wood fireplace. Kitchen, living room, dining room and 2 bedrooms have full lake view. 2 large screen tvs. Spa quality bath with whirlpool. Gas fireplace too!

4.97 out of 5 average rating, 290 reviews

Cottage in Oostburg

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

4.98 out of 5 average rating, 100 reviews

Loft in Sheboygan

Spacious/stylish, 2br loft

Lots of space, ready-to-use kitchen w/cooking essentials, washer/dryer in unit, 1.5 baths, 2 queen, 2 twin, ready for family/friends. Stocked with home essentials. 3 Smart TVs, free WIFI. Pay-as-you-go parking lot in rear but free nights/weekends. Wonderful, walkable neighborhood near shops, restaurants, art & children’s museum, river walk & lake front (a bit further). Short drive to Kohler, Whistling Straits golf course, Shops at Woodlake & Kohler Design Center. Marcus cinema near by.

4.96 out of 5 average rating, 131 reviews

Beach and golf house

This home is in the perfect location to explore everything Sheboygan County has to offer. It is located in the historic Ellis district on the shores of beautiful Lake Michigan. The home is a 2 or 3 minute walk to Deland Beach and the Sheboygan Marina and lighthouse. A short drive to world class golfing at Whistling Straights, Black Wolf Run and The Bull. Road America is also a short 20 minute drive. Located half way between Green Bay and Milwaukee for those Packer and Brewer fans.

4.96 out of 5 average rating, 158 reviews

Home in Oostburg

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 see thru log fired fireplace, screened in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and row boat are available for the boating enthusiast, with life jackets and other floating devices.

4.97 out of 5 average rating, 102 reviews

Chalet in Campbellsport

Long Lake Chalet

This recently remodeled and tastefully furnished, PET FRIENDLY, cabin boasts a unique charm. Nestled along the shores of Long Lake in the heart of the Kettle Moraine Forest, this lakefront property offers 45’ of serene, peaceful beauty. This stunning home features a large yard, pier access and year round recreational activities. Disconnect, unwind and take in all that Kettle Moraine has to offer. Whether vacationing with family or friends this retreat is waiting for you.

4.88 out of 5 average rating, 207 reviews

Condo in Sheboygan

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.

4.94 out of 5 average rating, 200 reviews

Beachfront getaway in Sheboygan

One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.