
Holiday rentals in Sheboygan
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Sheboygan
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Sheboygan holiday rentals
Other great holiday rentals in Sheboygan
Superhost

Home in Sheboygan
4.67 out of 5 average rating, 21 reviews6+ Guest Home
KyleRating, 5 stars3 months ago
Clean place, great location, great host. Very pleased with our stay, highly recommend
Guest favourite

Home in Sheboygan
5 out of 5 average rating, 16 reviewsBeautifully Renovated Historic Home at the Beach!
AmyRating, 5 stars16 months ago
Beautiful, well-appointed home with a heck of a view AND walking distance to downtown. Tricia was communicative and kind. Great experience!
Superhost

Flat in Sheboygan
4.5 out of 5 average rating, 12 reviewsSheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Christian DavidRating, 5 stars8 months ago
Excellent place, I was there for almost 2 months and is very peaceful, the place is exactly like photos, everything was great, Thank you Chris
Guest favourite

Home in Sheboygan
4.96 out of 5 average rating, 25 reviewsState Park w/ Orchard Style Yard & Pavilion
AnnaRating, 5 stars6 months ago
We had a great stay at The Orchard House Retreat. The property is as described, looks like the pictures and had everything we needed. The kids especially loved all the toys and books! The house is 5 min to the State Park beach and 10 min from downtown. We loved having the backyard, the furniture was well taken care of and the fire pit was perfect for s’mores. The hosts were very responsive and accommodating— with everything labeled around the home. It’s also a great layout for bigger families /groups with 2 bedrooms upstairs, 1 on the main floor and 1 in the basement.
Guest favourite

Apartment in Sheboygan
4.93 out of 5 average rating, 85 reviewsJanelle's Dockside Condo
BarbaraRating, 5 stars5 months ago
We want to stay here every year. Beautiful condo right on the water and within walking distance to coffee shop, restaurants and parks.
Top guest favourite

Home in Sheboygan
4.95 out of 5 average rating, 42 reviewsWander Back Inn to Sheboygan
LaurieRating, 5 stars2 weeks ago
We had a great time at this place. Everything was as described. Very easy to work with and accommodating.
Guest favourite

Home in Plymouth
5 out of 5 average rating, 5 reviewsRoad America & Golf Retreat
NickRating, 5 stars1 month ago
Great location for a relaxing weekend with the whole family. Would gladly visit again!
Superhost

Cabin in Cascade
4.83 out of 5 average rating, 30 reviewsLakefront Cabin on Private Lake Community
GregRating, 5 stars5 months ago
We had a fantastic stay at this cabin! It was spacious enough to comfortably accommodate three families, plus our dog and a little one. The location is perfect, nestled in a private gated community that offers a peaceful escape. The activities available were a highlight for us—fishing, paddle boarding, and kayaking kept everyone entertained and active. The scenery surrounding the cabin is absolutely beautiful, providing a perfect backdrop for our family gatherings. Overall, we had a memorable experience and would highly recommend this cabin for anyone looking for a fun and relaxing getaway with family and friends!
Quick stats about holiday rentals in Sheboygan
Total rentals
270 properties
Nightly prices starting at
£31 before taxes and fees
Total number of reviews
12K reviews
Family-friendly rentals
210 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
140 properties have a dedicated workspace
Destinations to explore
- Rentals with a patio Sheboygan
- Rentals with a washing machine and dryer Sheboygan
- House rentals Sheboygan
- Flat rentals Sheboygan
- Rentals with lake access Sheboygan
- Rentals with beach access Sheboygan
- Pet-friendly rentals Sheboygan
- Rentals with outdoor seating Sheboygan
- Family-friendly rentals Sheboygan
- Rentals with a fireplace Sheboygan
- Apartment rentals Sheboygan
- Rentals with a firepit Sheboygan
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Harrington Beach State Park
- Bradford Beach
- Milwaukee Country Club
- Pollock Community Water Park
- Pine Hills Country Club
- Blue Mound Golf and Country Club
- The Bull at Pinehurst Farms Golf Course
- Trout Springs Winery
- Green Bay Country Club Sports Center
- Heiliger Huegel Ski Club
- Sunburst
- Erin Hills Golf Course
- West Bend Country Club