Holiday Rentals in Sheboygan County

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Featured Holiday Rentals in Sheboygan County

Grandstay Residential Suites Hotel - Sheboygan
Lobby

Grandstay Residential Suites Hotel - Sheboygan

2.5 star property
8.6 out of 10, Excellent, (866)
"Friendly staff. Great room. Ample breakfast. "
The price is €118
includes taxes & fees
1 Dec - 2 Dec
Grandstay Residential Suites Hotel - Sheboygan
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Outdoor dining

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

9.8 out of 10, Exceptional, (229)
"This is a great place to stay! All the convenience of home and with an excellent view of the lake. Missing the sound of the waves already! There were binoculars to look out on the lake, games and puzzles, movies to watch. Close to shopping. Hour from Milwaukee or greenbay. It was a perfect place to stay and enjoy out visit with family close by. "
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Winter dates still available at Beachdaze!
On the beach, sun-loungers

Winter dates still available at Beachdaze!

10.0 out of 10, Exceptional, (123)
"We had such a wonderful time! The home was just perfect for the 4 of us- and with unexpected summer weather during a short fall weekend. The views and beach were incredible! It was so comfortable and clean, and had all the necessities and some extras. We look forward to coming back!"
Winter dates still available at Beachdaze!
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room
Miscellaneous

Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

9.4 out of 10, Exceptional, (183)
"We rented the house for a family trip. The house is large and has plenty of room for all. The house is in a perfect spot to watch the morning sunrise. It was nice to sit outside and use the fire pit. You can't beat the view at this house. The owner answers questions and is nice. We could recommend staying at this house."
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room
REMODELED HOME ON LAKE MICHIGAN
Property grounds

REMODELED HOME ON LAKE MICHIGAN

10.0 out of 10, Exceptional, (146)
"Great place"
REMODELED HOME ON LAKE MICHIGAN
Winter dates still available at Surfdaze!
Property grounds

Winter dates still available at Surfdaze!

10.0 out of 10, Exceptional, (94)
"We had a relaxing weekend on the lake. The bed was comfortable as were the couch and 2 chairs. The deck was a great place to sit and enjoy the sound and closeness of the lake. The windows offered full length views. It was just what we needed."
Winter dates still available at Surfdaze!
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Exterior

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

10.0 out of 10, Exceptional, (92)
"We absolutely loved our stay at the Sandalwood Cottage. We are a family of 5 (kids ages 5,4&2) and this was the perfect location! The house had everything we needed (kitchen supplies, towels, laundry, etc) it was exceptionally clean and close to all of the main Sheboygan attractions. We loved Bookworm Gardens and Above and Beyond Children’s Museum (both less than 15 minutes away). The yard was absolutely gorgeous and our kids had so much fun exploring the woods and playing on the swing set/tree...
The price is €155
includes taxes & fees
3 Dec - 4 Dec
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
The RandomCabin “On Random Lake”
Property grounds

The RandomCabin “On Random Lake”

9.8 out of 10, Exceptional, (45)
"This house and it’s location is perfect for quick getaway for the weekend. Dan was a great host with quick communication on check in and any other questions we had. Very close to a few establishments all with great friendly locals. We will definitely be back. "
The RandomCabin “On Random Lake”
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Private kitchen

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

10.0 out of 10, Exceptional, (11)
"Great spot for the fellas to crash during our golf getaway. Spacious and the beds were comfy. Easy walk to food and drinks. Thanks for being part of a memorable trip."
The price is €444
includes taxes & fees
3 Dec - 4 Dec
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
*NEW* Sleeps 8 & Spacious!
Smart TV, books

*NEW* Sleeps 8 & Spacious!

10.0 out of 10, Exceptional, (18)
"Not much to look at on the outside but inside was great! Location was great in town, clean and good beds and hot showers"
The price is €322
includes taxes & fees
2 Dec - 3 Dec
*NEW* Sleeps 8 & Spacious!
Beach front luxury spacious villa !
Fireplace, books

Beach front luxury spacious villa !

10.0 out of 10, Exceptional, (48)
"This house was beautiful! The pictures are exactly what you get. House was very clean. Probably the cleanest house we've ever stayed in. Location was amazing. It is right on the beach! Spectacular views of Lake Michigan. Walking distance to restaurants, coffee shop, Blue Harbor resort and a very nice walking trail. Loved our stay!"
Beach front luxury spacious villa !
3 Bedroom Beach House
Golf

3 Bedroom Beach House

9.6 out of 10, Exceptional, (10)
"We had a great time going back to Sheboygan. We did lots of sightseeing, swimming, enjoying the sand on the beach. We ate a lot of great food!"
3 Bedroom Beach House
Farmhouse Designed Apt With Entertainment Room
Fridge, microwave, oven, stovetop

Farmhouse Designed Apt With Entertainment Room

10.0 out of 10, Exceptional, (45)
"Location was excellent and the place had everything we could need. The only downside I can think of was that the AC didn't quite keep up on real hot day. I'd stay here again."
Farmhouse Designed Apt With Entertainment Room
Start planning now for the holidays-neutral spot to celebrate with family!
View from property

Start planning now for the holidays-neutral spot to celebrate with family!

10.0 out of 10, Exceptional, (79)
"Great location"
Start planning now for the holidays-neutral spot to celebrate with family!
Family-Friendly House: Walk to Lake Michigan!
Fridge, microwave, stovetop, dishwasher

Family-Friendly House: Walk to Lake Michigan!

9.6 out of 10, Exceptional, (16)
"Very happy with the house we rented, it was very clean, well stocked, and great location. Definitely will recommend!"
Family-Friendly House: Walk to Lake Michigan!
Beautiful country home (3800 sq ft) on 4 acres with river frontage - 8 beds!
Outdoor dining

Beautiful country home (3800 sq ft) on 4 acres with river frontage - 8 beds!

10.0 out of 10, Exceptional, (72)
"Great place to get away and relax and enjoy fall weather. House has everything you could need for the family. Very clean and well kept. Plenty of entertainment options and just 12 minutes from things to do around the area. Very close for golfers as well. Really enjoyed our time and the home."
Beautiful country home (3800 sq ft) on 4 acres with river frontage - 8 beds!
Summit Road Estate - Top Luxury
Terrace/patio

Summit Road Estate - Top Luxury

9.6 out of 10, Exceptional, (5)
"Our stay was phenomenal. The pool and the hot tub were such a plus. The house was super clean and had ample towels and blankets for us to use. The giant kitchen was equipped with all the necessities to make homemade meals. We did have an incident where there was a mouse in the master bedroom but was able to get it out of the house."
Summit Road Estate - Top Luxury
Welcome to the "Lake Cottage" where lake Michigan waves are calling
Miscellaneous

Welcome to the "Lake Cottage" where lake Michigan waves are calling

10.0 out of 10, Exceptional, (121)
"This is my third time at the cabin and it never ceases to amaze me. Alan and Linda provide all of the perfect little personal touches and are easily available for questions if needed! I get my best sleep at this cabin and always go home the most relaxed I can be. Thank you again, Alan & Linda! "
Welcome to the "Lake Cottage" where lake Michigan waves are calling
Secluded Lake House Retreat - Book Now!
Interior

Secluded Lake House Retreat - Book Now!

9.2 out of 10, Wonderful, (40)
"Very nice! A small, clean cabin with modern updates, on the water and a short drive to Appleton. "
Secluded Lake House Retreat - Book Now!
Lake Winnebago Waterfront Cottage W/Hot Tub
Outdoor dining

Lake Winnebago Waterfront Cottage W/Hot Tub

10.0 out of 10, Exceptional, (144)
"The property overall was so much more than what you read and see on the listing. I’ve stayed at countless properties on VRBO and other platforms. Jason was the host we all want. Communicative, helpful, professional, and friendly. Private lake access just steps away. A perfectly placed hot-tub. The inside of the home makes a perfect getaway for couples or families. I’m immeasurably grateful for Jason and everything he’s done to make this a destination that I look forward to visiting...
Lake Winnebago Waterfront Cottage W/Hot Tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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