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Sheboygan Area Rentals

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From $1152 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 $1152 per night (USD)
VRBO
From $652 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 $652 per night (USD)
Expedia
From $1566 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 $1566 per night (USD)
VRBO
From $311 per night (USD)
VRBO
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, ...
From $311 per night (USD)
VRBO
From $396 per night (USD)
VRBO
Riverwoods Retreat | Game Room, Hot Tub & Sauna
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Escape to Riverwoods Retreat, a luxury getaway in the heart of Sheboygan County! Just minutes from Road America, Elkha ...
From $396 per night (USD)
VRBO
From $610 per night (USD)
Expedia
Edgewater Escape: 4 Bedroom, Sleeps 14!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
This is your new favorite vacation spot. A spacious, two-level condo located just across the courtyard from the beautifu ...
From $610 per night (USD)
Expedia
From $610 per night (USD)
VRBO
Just Beachy: 4 Bedroom, Sleeps 12!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Your Lakeside Escape Awaits Discover your perfect getaway in this cozy, two-level condo, just steps from the sandy shore ...
From $610 per night (USD)
VRBO
From $846 per night (USD)
VRBO
Charming 3-bedroom house in downtown Elkhart Lake
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Your cozy getaway awaits in Elkhart Lake at this newly-renovated historic house. Unwind in 3 spacious bedrooms including ...
From $846 per night (USD)
VRBO
From $131 per night (USD)
VRBO
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)
VRBO
From $516 per night (USD)
Expedia
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 $516 per night (USD)
Expedia
From $285 per night (USD)
VRBO
>>The Daydream Lodge<< @Racers Ridge
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Relaxing.Racing.Golfing. Exploring. This spacious 3 bedroom home is perfect for a tranquil getaway or as a base camp fo ...
From $285 per night (USD)
VRBO
From $193 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 $193 per night (USD)
Expedia
From $193 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 $193 per night (USD)
VRBO
From $729 per night (USD)
Expedia
4- Bedroom Retreat with Sauna, Game Room, Patio & Walk to 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 $729 per night (USD)
Expedia
From $193 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 $193 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Walk to Road America-Private Getaway with Views + Loft + Fire Pit
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The Hillside cottage is located just steps from Road America. It offers one of the few walkable stays to the track while ...
From $251 per night (USD)
Expedia
$3 Min to Road America, \Amazing Location!!\$
From $830 per night (USD)
VRBO
3 Min to Road America, \"Amazing Location!!\"
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 $830 per night (USD)
VRBO
From $374 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 $374 per night (USD)
Expedia
From $193 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 $193 per night (USD)
VRBO
From $193 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 $193 per night (USD)
Expedia
From $193 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 $193 per night (USD)
VRBO
From $193 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 $193 per night (USD)
Expedia
From $1226 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 $1226 per night (USD)
VRBO
From $1184 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 $1184 per night (USD)
VRBO
From $523 per night (USD)
VRBO
Sheboygan Shores
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 $523 per night (USD)
VRBO
From $747 per night (USD)
VRBO
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, surrou ...
From $747 per night (USD)
VRBO
From $542 per night (USD)
VRBO
Cozy Crystal Lakefront Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Spacious 4BR Lakefront Cottage on Crystal Lake – Sleeps 14, Near Elkhart Lake! Enjoy the perfect lake getaway in this c ...
From $542 per night (USD)
VRBO
From $397 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 $397 per night (USD)
VRBO
From $327 per night (USD)
VRBO
Lake Breeze Cottage. One 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 $327 per night (USD)
VRBO
From $564 per night (USD)
Expedia
Hot Tub, Kayaks, SUP's & 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 $564 per night (USD)
Expedia
From $239 per night (USD)
VRBO
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 $239 per night (USD)
VRBO
From $401 per night (USD)
Expedia
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 $401 per night (USD)
Expedia
From $650 per night (USD)
VRBO
The Lakeside Duo | Side-By-Side Beachfront Condos
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
Perfect for large families or groups, this listing includes two side-by-side beachfront condos with full access to both ...
From $650 per night (USD)
VRBO
From $462 per night (USD)
Expedia
Lakeside Daydream - Walk to Lake Michigan!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Lakeside Daydream — Presented by Great Lakes Getaways! Relax in this cozy 2BR, 1BA home just a short walk ...
From $462 per night (USD)
Expedia
From $675 per night (USD)
VRBO
Captain`s Quarters | Lake Michigan views for 14
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
CAPTAIN’S QUARTERS | LAKE MICHIGAN GROUP RETREAT Wake to panoramic Lake Michigan sunrises at Captain’s Quarters, a refi ...
From $675 per night (USD)
VRBO
From $1028 per night (USD)
VRBO
Beautiful Upscale Countryside 4-Bedroom Retreat near Road America
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to The Glasshouse, a stunning custom-built Craftsman home set on nearly 6 private acres of rolling Wisconsin cou ...
From $1028 per night (USD)
VRBO
From $922 per night (USD)
VRBO
Villa von Baumbach - Trade Screens for Stories
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Step Into Another Era on Elkhart Lake There are thousands of vacation rentals with fast Wi-Fi, giant televisions, and mo ...
From $922 per night (USD)
VRBO
From $500 per night (USD)
Expedia
Elkhart Lake Fun in the Sun
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Vacation in style at our luxurious Elkhart Lake retreat! This spacious 4-bedroom duplex comfortably accommodates up to 1 ...
From $500 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unplug and relax in this colorful 3 bedroom home, just steps from restaurants, bakery & sports bar & bakery. You will f ...
From $285 per night (USD)
VRBO
From $890 per night (USD)
Expedia
Elkhart Lake Home w/ Fishing Dock! Family Escape
Bedrooms:
2
Bathrooms:
5
Sleeps:
14
3 Mi to Road America | Furnished Deck for Cookouts | 2,400 Sq Ft Race weekends and lake adventures— this vacation rent ...
From $890 per night (USD)
Expedia
From $375 per night (USD)
VRBO
Sleeps 13 - Hot Tub - Game Room - minutes from Road America
Bedrooms:
2
Bathrooms:
3
Sleeps:
13
Enjoy the peace of nature, along with the convenience of easy access to Plymouth and surrounding attractions, including ...
From $375 per night (USD)
VRBO
From $730 per night (USD)
VRBO
Luxury Pool Retreat - 2 Acres - Near Whistling Straits
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Private, upscale retreat on ~2 acres, perfect for golf trips, group getaways and summer stays. Located minutes from Whi ...
From $730 per night (USD)
VRBO
From $168 per night (USD)
VRBO
Peaceful Home Base: Comfy Beds: Road America, Golf & Lake Michigan
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This classic 2 BR ranch house is the perfect homebase for your trip to Sheboygan County. Perfect for a couples retreat ...
From $168 per night (USD)
VRBO
Click For Pricing
Expedia
Beachside Beautifully Renovated Historic Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Take a walk right out your door and onto Sheboygan's North Pier to visit the famed red Light House. Then come back to ...
Click For Pricing
Expedia
From $4852 per night (USD)
VRBO
Shoreland Farm | Runoffs HQ + Indoor Pool
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Indoor pool + hot tub, private lake access, and 12 secluded acres just minutes from Elkhart Lake and Road America. This ...
From $4852 per night (USD)
VRBO
From $393 per night (USD)
Expedia
Walkable Lake Escape! Elkhart Lake Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beach Access | 3 Mi to Road America | Pet Friendly w/ Fee Craving lake days, local flavors, and a slower small-town pac ...
From $393 per night (USD)
Expedia
From $228 per night (USD)
VRBO
Fresh Coast Craftsman - Pet Friendly | Near Lake
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
New Listing! Fresh Coast Craftsman by Great Lakes Getaways Welcome to your private 2-bedroom, 1-bath entire home retr ...
From $228 per night (USD)
VRBO
From $495 per night (USD)
Expedia
Woodsy Plymouth Hideaway: Hot Tub & Game Room
Bedrooms:
2
Bathrooms:
3
Sleeps:
14
Hot Tub | Vintage Fireplace | Ping-Pong, Foosball & Dartboard Welcome to 'Highland Hideaway' — eclectic, inviting, and ...
From $495 per night (USD)
Expedia
From $558 per night (USD)
VRBO
Condo in the heart of Elkhart Lake with Private Pool and Beach access!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to The Victorian Inn Grand Suite at Elkhart Lake! Escape to our uniquely designed one-bedroom, one-bath condo ...
From $558 per night (USD)
VRBO
From $254 per night (USD)
Expedia
At River's Edge | 2BR River Retreat with Garage
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Riverside Drift — Presented by Great Lakes Getaways! Escape to this spacious 2BR, 1.5BA Sheboygan retreat ...
From $254 per night (USD)
Expedia
From $309 per night (USD)
VRBO
NEW Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
This riverfront loft truly offers the best combination of views and location in Sheboygan. Situated right on the boar ...
From $309 per night (USD)
VRBO
From $313 per night (USD)
VRBO
Fits 7! Beachfront Condo - Handicap Accessible
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to your Lake Michigan getaway - a bright, modern condo sitting right on Sheboygan's sandy shore line. Wake up to ...
From $313 per night (USD)
VRBO
From $435 per night (USD)
VRBO
Amazing 5-bedroom Victorian house Downtown Plymouth 6 minutes from Road America
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
The Vibrant Victorian ~ Downtown Plymouth was restored in fall of 2025-2026 and we focused on creating a unique downtown ...
From $435 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Riverfront Condo Steps to Downtown & Lake Michigan
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our beautiful riverfront condo located in Sheboygan's South Pier District. This bright second-story condo off ...
From $398 per night (USD)
Expedia
From $440 per night (USD)
VRBO
“Stanley's Cozy Beach Cottage – Steps from the Shore”
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to your private, lakesidel retreat! This charming, rustic 3-bedroom, 1 bath cottage offers the perfect blend of ...
From $440 per night (USD)
VRBO
From $521 per night (USD)
Expedia
Walk to Beach & Pier | Fully-Loaded Kitchen
Bedrooms:
4
Bathrooms:
5
Sleeps:
11
✨ Welcome to the Huron House, hosted by Sheboygan Vacation Rentals ✨ A beautiful classy remodeled 5-bedroom, 4-bath hom ...
From $521 per night (USD)
Expedia
From $473 per night (USD)
VRBO
Walk to Downtown & Elkhart Lake | Firepit
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tucked into the heart of Elkhart Lake, our Maple Street House , hosted by Sheboygan Vacation Rentals, puts you just a sh ...
From $473 per night (USD)
VRBO
From $553 per night (USD)
Expedia
Lake | Walk Everywhere | 3BR Elkhart Beach Resort
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Stay Together at Elkhart Lake Beach Resort | 3BR Lakeview Condo for Couples & Friends Skip the split hotel rooms—this r ...
From $553 per night (USD)
Expedia
From $164 per night (USD)
VRBO
Victorian Inn #239 | 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $164 per night (USD)
VRBO
From $172 per night (USD)
Expedia
Victorian Inn #114 | 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $172 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Victorian Inn #245 | 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $169 per night (USD)
VRBO
From $180 per night (USD)
Expedia
Victorian Inn #120 | King Bed + Full Sleeper Sofa
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $180 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Victorian Inn #116 | 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $187 per night (USD)
VRBO
From $167 per night (USD)
Expedia
Victorian Inn #246 | 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $167 per night (USD)
Expedia
From $206 per night (USD)
VRBO
Victorian Inn #107 | King Bed + Queen Sleeper Sofa
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $206 per night (USD)
VRBO
From $554 per night (USD)
Expedia
Two Private Spaces | Downtown & Near Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your downtown Sheboygan retreat, hosted by Sheboygan Vacation Rentals. This unique property offers two though ...
From $554 per night (USD)
Expedia
From $174 per night (USD)
VRBO
Victorian Inn #240 | 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $174 per night (USD)
VRBO
From $168 per night (USD)
Expedia
Victorian Inn #113 | 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $168 per night (USD)
Expedia
From $164 per night (USD)
VRBO
Victorian Inn #244 | King Bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $164 per night (USD)
VRBO
From $171 per night (USD)
Expedia
Victorian Inn #117 | King Bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $171 per night (USD)
Expedia
From $174 per night (USD)
VRBO
Victorian Inn #241 | 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $174 per night (USD)
VRBO
From $169 per night (USD)
Expedia
Victorian Inn #118 | King Bed + Full Sleeper Sofa
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $169 per night (USD)
Expedia
From $164 per night (USD)
VRBO
Victorian Inn #242 | King Bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $164 per night (USD)
VRBO
From $168 per night (USD)
Expedia
Victorian Inn #247 | 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $168 per night (USD)
Expedia
From $180 per night (USD)
VRBO
Victorian Inn #119 | King Bed + Full Sleeper Sofa
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $180 per night (USD)
VRBO
From $188 per night (USD)
Expedia
Victorian Inn #115 | 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $188 per night (USD)
Expedia
From $410 per night (USD)
VRBO
Private Studio | Walk to Restaurants, Cafés & Downtown Sheboygan
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to the The 8th Street ADU, hosted by Sheboygan Vacation Rentals. Our newly designed studio apartment at Huron & ...
From $410 per night (USD)
VRBO
From $425 per night (USD)
Expedia
The Victory Lap - Family Friendly Sleeps 10
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Spacious 3-bedroom, 2.5-bath home in a Victorian Village condo, inside of Elkhart Lake. Sleeps up to 10 guests with 7 be ...
From $425 per night (USD)
Expedia
From $391 per night (USD)
VRBO
Escape from the Track - Massage Chair | Fire Pit!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape the Track & Relax in Style! Just minutes from Elkhart Lake, this spacious Plymouth retreat is perfect for race we ...
From $391 per night (USD)
VRBO
From $500 per night (USD)
Expedia
Windward House - Entire home in Sheboygan
Bedrooms:
3
Bathrooms:
1
Sleeps:
6
Just steps from the Sheboygan Yacht Club and beautiful Deland Park with its sandy beach. This charming brick getaway put ...
From $500 per night (USD)
Expedia
From $472 per night (USD)
VRBO
Winner`s Circle | Luxury Stay Near Road America
Bedrooms:
3
Bathrooms:
1
Sleeps:
6
The Winner’s Circle Townhouse is a luxury retreat perfectly located just steps from Road America and minutes from Elkhar ...
From $472 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Sunset Vista- cozy two bedroom retreat
Bedrooms:
2
Bathrooms:
1
Sleeps:
7
This cozy vacation rental is the perfect place to relax and unwind! Enjoy a warm and inviting fireplace, comfy furnishin ...
From $396 per night (USD)
Expedia
From $439 per night (USD)
VRBO
Blueberry Hill - Entire Home in Plymouth
Bedrooms:
2
Bathrooms:
1
Sleeps:
9
Entire Home in Plymouth - this charming getaway offers the perfect balance of convenience and tranquility. Surrounded by ...
From $439 per night (USD)
VRBO
From $460 per night (USD)
Expedia
Apex One – Steps from Road America Racetrack
Bedrooms:
3
Bathrooms:
1
Sleeps:
4
Experience the ultimate getaway at this charming 2-bedroom, 3-bath townhome perfectly situated just steps from the main ...
From $460 per night (USD)
Expedia
From $403 per night (USD)
VRBO
The Lighthouse at Lake Ellen
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to this spacious and relaxing 3-bedroom, 2-bath cottage located directly across from beautiful Lake Ellen in Casc ...
From $403 per night (USD)
VRBO
From $637 per night (USD)
Expedia
The Cabin on Kettlewood Acres
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to The Cabin on Kettlewood Acres tucked among rolling kettles and quiet woods. Relax on the front porch swing, si ...
From $637 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Victorian Inn #111 | Queen Murphy Bed + Sofa Bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $211 per night (USD)
VRBO
From $381 per night (USD)
Expedia
A Glorious Getaway Sheboygan - LUX Lake Condo
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Glorious Getaway — Presented by Great Lakes Getaways! Unwind in this spacious 4-bedroom, 3-bath beachfron ...
From $381 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Waterfront Sheboygan Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Welcome to your Lake Michigan, Sheboygan Getaway - riverfront condo sitting right on Sheboygan's riverfront board walk a ...
From $355 per night (USD)
VRBO
From $744 per night (USD)
Expedia
All-Season Lodge 40 Acres: Walk to Elkhart Lake!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Ice Fishing & Skiing Nearby | Wildlife Viewing | 1 Mi to Ice Age Trail | 2 Mi to Road America Every season is an advent ...
From $744 per night (USD)
Expedia
From $162 per night (USD)
VRBO
New Victorian Inn #243 | King Bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $162 per night (USD)
VRBO
From $464 per night (USD)
Expedia
SchoolHouse Pent-House
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome back to school! This rustic remodel of 1925 schoolhouse has two full apartments, rented together as one large sp ...
From $464 per night (USD)
Expedia
From $343 per night (USD)
VRBO
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Eve’s Place is a clean, comfortable space ideal for families and couples visiting Sheboygan for the beach or downtown. P ...
From $343 per night (USD)
VRBO
From $675 per night (USD)
Expedia
Elkhart Lake - Checkered Flag
Bedrooms:
1
Bathrooms:
4
Sleeps:
11
You’ll be close to everything when you stay at this centrally-located home in Elkhart Lake! Experience it all with a 2 m ...
From $675 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Victorian Inn #226 | 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake offering a private room. Enjoy the perfect blend of comfort, convenienc ...
From $208 per night (USD)
VRBO
From $1385 per night (USD)
VRBO
A Private Retreat Near Road America, Walk to Downtown Elkhart Lake, Sleeps 12
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Now accepting inquiries for Summer 2027 and Road America event weeks. Welcome to one of Elkhart Lake's most unique and ...
From $1385 per night (USD)
VRBO
From $208 per night (USD)
VRBO
Victorian Inn #233 | King Bed + Queen Sleeper Sofa
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Stay at Victorian Village Resort in Elkhart Lake and enjoy a comfortable private room just minutes from everything. Rela ...
From $208 per night (USD)
VRBO

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Results: 297 Rentals