Cruise And Resorts - Vacation Rentals in Sheboygan

Boat in Sheboygan Harbor for Mercury Midwest Challenge! From US $434
         

Luxury Places to Stay in Sheboygan

Over 786+ Luxury Places to Stay in or Near Sheboygan
Beautiful Home To Enjoy Your Experience From US $2,125
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygann From US $1,427
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Experience Gracious Living & Destination Kohler From US $1,380
         

Top-Rated Vacation Rentals with a Pool in Sheboygan

Over 99+ Top-Rated Vacation Rentals with a Pool in or Near Sheboygan
Gather Your Group at the Bunkhouse! From US $915
         

10.0 (46 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool
Private Beach, Pools & Full-Kitchen From US $173
         

10.0 (8 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX From US $1,252
         

Upscale Waterfront and Pool View Condo! From US $408
         

10.0 (4 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Sheboygan

Over 190+ Pet-Friendly Vacation Rentals in or Near Sheboygan
Harbor Town Inn, BW Signature Collection From US $81
         

9.0 (1007 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Riverfront Getaway From US $268
         

10.0 (44 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Sheboygan

Over 190+ Large Vacation Homes & Villas in or Near Sheboygan
Riverfront Retreat! Water front and dog friendly! From US $156
         

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10.0 (4 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
'Ania's Retreat' w/Deck: Walk to Lake Michigan! From US $158
         

Beach front luxury spacious villa ! From US $314
         

10.0 (75 Reviews)
Villa
  • Air Conditioner
  • Parking
  • View

Wheelchair Accessible Vacation Homes in Sheboygan

Over 49+ Wheelchair Accessible Vacation Homes in or Near Sheboygan
Malibu of the Midwest Condo steps from the Lake From US $249
         

Lake Orchard Farm Retreat From US $195
         

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8.9 (43 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View
Watershed Hotel From US $136
         

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9.6 (465 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home From US $260
         

Modern South Pier Condo on Sheboygan River! From US $229
         

9.4 (33 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Corner River Walk Condo with Spectacular Views From US $249
         

10.0 (45 Reviews)
Condo
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace

Sheboygan Varoom and Airbnb Places to Stay Under $200

Over 264+ Sheboygan Varoom and Airbnb Places to Stay Under $200
Plymouth Rock Camping Resort From US $149
         

7.8 (33 Reviews)
RV Rental
  • Air Conditioner
  • Parking
  • Pool
Gleason's Chouse From US $138
         

10.0 (41 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Home Away from Home From US $150
         

10.0 (35 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Riverfront Sheboygan Townhome w/Grill! From US $167
         

10.0 (29 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
BEACHSIDE GETAWAY IN SHEBOYGAN From US $153
         

10.0 (27 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Tina's bungalow From US $114
         

10.0 (26 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Sheboygan

Over 426+ Instantly Bookable Vacation Homes in or Near Sheboygan
REMODELED HOME ON LAKE MICHIGAN From US $212
         

9.8 (159 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown. From US $131
         

9.6 (11 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Lake Michigan Vacation Rental: 1 Block to Marina! From US $233
         

7.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
One Minute to Road America - Close to PGA Golfing From US $436
         

Beach and Golf House From US $364
         

10.0 (70 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Peaceful Cottage on Lake Michigan From US $274
         

10.0 (69 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV

About Sheboygan Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cruiseandresorts Sheboygan, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Sheboygan. Places to stay near Sheboygan with prices averaging $434 a night.

Cruiseandresorts makes it easy and safe to find and compare vacation rentals in Sheboygan with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Sheboygan

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Use these Quick Filters to Find a Vacation Rental in Sheboygan

Pro Tip: Cruiseandresorts makes it easy to compare the best listings on Cruiseandresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruiseandresorts homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Sheboygan.

Weather in Sheboygan

View the weather forecast for Sheboygan before booking your Sheboygan Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F