Sheboygan Area, Wisconsin Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Sheboygan Area, Wisconsin on RentalSaver.com!

Sheboygan Area Rentals

From $136 per night (USD)
VRBO
2 Mi to Dtwn: Studio Suite in Sheboygan
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Pet Friendly w/ Fee | Walk to Diner & Brewery | Private Balcony Set sail for a getaway near the shore of Lake Michigan ...
From $136 per night (USD)
VRBO
From $1438 per night (USD)
VRBO
Beautiful Lake House with private access to Elkhart Lake
Bedrooms:
3
Bathrooms:
8
Sleeps:
18
Escape to our serene lake house, perfectly nestled on the shores of Elkhart Lake– a peaceful oasis ideal for families, c ...
From $1438 per night (USD)
VRBO
From $458 per night (USD)
VRBO
Home Near Road America & Elkhart Lake
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Close to Village Square | Pinball & Arcade Machine | Community Car Wash Bay Whether you’re here for lakefront fun or ex ...
From $458 per night (USD)
VRBO
From $505 per night (USD)
Expedia
Lake House-Kayaks/Paddle Boards/Private Pier
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
🌅 Luxury Lakefront Living w/ Private Pier, Kayaks, & More on Crystal Lake Welcome to the Crystal Lake Beauty hosted by ...
From $505 per night (USD)
Expedia
From $1304 per night (USD)
VRBO
Road America Retreat: Modern Villa w/ Garage!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Race-Week Ready | Dog Friendly w/ Fee | Motorsports Villas Rest days or race days — this Elkhart Lake vacation rental m ...
From $1304 per night (USD)
VRBO
Click For Pricing
Expedia
Charming, Modern Riverfront 2-bedroom South Pier, Sheboygan Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stay comfortably in Sheboygan at this 2-bedroom condo. The space features 2 lovely queen beds, 2 bathrooms with showers, ...
Click For Pricing
Expedia
From $250 per night (USD)
VRBO
Near Hiking: Lakefront Getaway in Campbellsport!
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
Nestled on 1.5 Acres | Pet Friendly w/ Fee | Families Welcome | BBQ Ready Escape from the hustle and bustle of daily li ...
From $250 per night (USD)
VRBO
From $231 per night (USD)
Expedia
NEW! Harbor Hideaway - Walk to Beach, Dining & Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy Condo Steps from Sheboygan Harbor – Walk to Beach, Dining & Downtown Perfectly situated just steps from the Sheb ...
From $231 per night (USD)
Expedia
From $385 per night (USD)
VRBO
Edgewater Escape: 4 Bedroom, Sleeps 14!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
This two-story 4 bedroom/3 bathroom get-away is in close proximity to EVERYTHING, including the boardwalk, harbor and do ...
From $385 per night (USD)
VRBO
From $623 per night (USD)
Expedia
Just Beachy: 4 Bedroom, Sleeps 12!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Newly Renovated 4BR/3BA Upper-Level Condo – Walk to Boardwalk, Harbor & More! Welcome to your perfect home away from ho ...
From $623 per night (USD)
Expedia
From $541 per night (USD)
VRBO
Charming 3-bedroom house seconds to downtown Elkhart
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Your cozy getaway awaits in Elkhart Lake at this newly-renovated historic house. Unwind in 3 bedrooms including a spacio ...
From $541 per night (USD)
VRBO
From $131 per night (USD)
Expedia
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Sheboygan at this beautiful upper unit duplex . This nice space features 1 bedroom with a co ...
From $131 per night (USD)
Expedia
From $483 per night (USD)
VRBO
Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
Escape to Sheboygan Chalet—a stunning modern retreat tucked in the woods of the Black River community 🌲 Just two blocks ...
From $483 per night (USD)
VRBO
From $204 per night (USD)
VRBO
9 Mi to Shore: Home w/ Hot Tub in Howards Grove!
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Spacious Yard | Cookout Ready | Modern Interior The ideal Wisconsin escape is just a click away at this cozy vacation r ...
From $204 per night (USD)
VRBO
From $761 per night (USD)
VRBO
Private Beach on Lake Michigan: Oostburg Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Expansive Lake Views | 11 Mi to Family Fun in Sheboygan | Waterfront Dining Unplug, unwind, and soak up the slower pace ...
From $761 per night (USD)
VRBO
From $297 per night (USD)
Expedia
1st Floor Double Suite Courtyard View
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
WELCOME RACE FANS AND VACATIONERS!! The Victorian Inn is located along a picturesque freshwater lake and beach, and with ...
From $297 per night (USD)
Expedia
From $130 per night (USD)
VRBO
Apartment Centrally Located
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $130 per night (USD)
VRBO
From $130 per night (USD)
Expedia
Apartment Centrally Located
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $130 per night (USD)
Expedia
From $130 per night (USD)
VRBO
Apartment Centrally Located
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $130 per night (USD)
VRBO
From $496 per night (USD)
Expedia
4- Bedroom Retreat w/ Sauna, Game Room, Patio & Walk to Golf, Bars & Restaurants
Bedrooms:
2
Bathrooms:
4
Sleeps:
13
This newly renovated home offers the ultimate blend of comfort, fun, and convenience. Located in the heart of the city, ...
From $496 per night (USD)
Expedia
From $130 per night (USD)
VRBO
Apartment Centrally Located
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $130 per night (USD)
VRBO
From $260 per night (USD)
Expedia
The Historic Downtown Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Located in Sheboygan Falls, this adorable apartment offers 2 cozy bedrooms with queen beds, a lovely bathroom with a bat ...
From $260 per night (USD)
Expedia
From $250 per night (USD)
VRBO
The Hillside Cottage- 2 min Walk to Road America!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The Hillside Cottage is the perfect location for anyone visiting Elkhart Lake, Road America, or the many different golf ...
From $250 per night (USD)
VRBO
From $1239 per night (USD)
VRBO
GRAND VILLA Luxury 5-Bed Motorsport Retreat–1 Mi to Road America & Elkhart Lake
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
GRAND VILLA | Luxury 5-Bed Motorsport Retreat – 1 Mile to Road America & Elkhart Lake Sleeps: 10 | Bedrooms: 5 | Bathro ...
From $1239 per night (USD)
VRBO
From $770 per night (USD)
VRBO
3 Min to Road America, outdoor deck, grill, & fire table
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Be one of the first to stay at this newly renovated 5-bedroom, 2.5-bath home. Plenty of space for group getaways, race w ...
From $770 per night (USD)
VRBO
From $319 per night (USD)
Expedia
Brand New 3-bedroom Home in Random Lake with office, quick walk to the beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to the Dead End Dreamhouse—a peaceful, modern retreat built in 2023. Located at the end of a quiet street, this ...
From $319 per night (USD)
Expedia
From $130 per night (USD)
VRBO
Apartment Centrally Located
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $130 per night (USD)
VRBO
From $130 per night (USD)
Expedia
Apartment Centrally Located
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $130 per night (USD)
Expedia
From $130 per night (USD)
VRBO
Apartment Centrally Located
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $130 per night (USD)
VRBO
From $130 per night (USD)
Expedia
Apartment Centrally Located
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $130 per night (USD)
Expedia
From $752 per night (USD)
VRBO
Walk to Beaches + Restaurants: Elkhart Lake Escape
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome Basket | Home Gym | Golf Course On-Site Whether you’re planning a memorable family retreat or fun-filled getawa ...
From $752 per night (USD)
VRBO
From $1048 per night (USD)
VRBO
Fountainhead Sanctuary in Elkhart Lake/RA: Spacious 4-bdrm house, amazing
Bedrooms:
2
Bathrooms:
5
Sleeps:
14
Fountainhead is more than a place to stay—it’s a nature retreat set on 21 serene acres in the Kettle Moraine. Named for ...
From $1048 per night (USD)
VRBO
From $498 per night (USD)
VRBO
Fully renovated, updated, and high-end finished 5 bedroom facing the marina!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
No expense spared in this fully renovated, updated, and high-end finished home facing the water and a block from the bea ...
From $498 per night (USD)
VRBO
From $639 per night (USD)
Expedia
Lakeview Farm | Beach · Hot Tub · Theater · Views
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Lakeview Farm · 6BR · Sleeps 14 🌊 Private Lake Michigan beach—your private oasis 🎬 Theater w/ laser projector, sur ...
From $639 per night (USD)
Expedia
From $501 per night (USD)
VRBO
Cozy Crystal Lakefront Cottage
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Spacious 4BR Lakefront Cottage on Crystal Lake – Sleeps 14, Near Elkhart Lake! Enjoy the perfect lake getaway in this c ...
From $501 per night (USD)
VRBO
From $300 per night (USD)
VRBO
Pet-Friendly 3BR Retreat!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Relaxing 3-Bedroom Retreat Near Lake Michigan – Pet Friendly! Welcome to your perfect home base in Sheboygan! This spac ...
From $300 per night (USD)
VRBO
$Lake Breeze Cottage. \nOne block from the lake, walking distance to downtown!$
From $229 per night (USD)
VRBO
Lake Breeze Cottage. \nOne block from the lake, walking distance to downtown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Lake Breeze Cottage, your year-round getaway just one block from the sparkling shores of Lake Michigan. Wheth ...
From $229 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Crystal Clear Lake, Hot Tub, Kayaks, SUP & Firepit
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
🌅 Panoramic Gold Coast Sunsets from Hilltop Windows 🛁 Private Hot Tub on Spacious Lakeview Deck 🚣 Kayaks & SUP Boards ...
From $416 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Large Backyard, Walk to Hospital: Sheboygan Abode!
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Mid-Term Stays & Travel Nurses Welcome | Near Fishing & Golf | WFH Friendly Whether you're here for work or play, you'l ...
From $222 per night (USD)
VRBO
From $140 per night (USD)
Expedia
Surfside Retreat – Walk to Lake
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Perfectly located near downtown Sheboygan and just one block from Lake Michigan, this home offers everything a traveler ...
From $140 per night (USD)
Expedia
From $136 per night (USD)
VRBO
Storybook 2-bedroom apartment 1mi from Lake Michigan
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to The Fox & Folly Inn —a unique whimsical retreat. Perfect for families and those who are kids at heart! • Cr ...
From $136 per night (USD)
VRBO
From $177 per night (USD)
Expedia
Sheboygan Riverside Condo
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Experience the Malibu of the Midwest in this stunning 2-bedroom retreat! The king suite offers a private balcony with a ...
From $177 per night (USD)
Expedia
From $181 per night (USD)
VRBO
The Beach town bungalow
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Cozy second-floor Airbnb in Sheboygan, WI, the “Malibu of the Midwest.” 2-bed, 1-bath with queen master, bunk room, full ...
From $181 per night (USD)
VRBO

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Sheboygan Area Rentals

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Results: 343 Rentals