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 $742 per night (USD)
VRBO
1-Mile to Road America, 2-Miles to Elkhart Lake
Bedrooms:
3
Bathrooms:
7
Sleeps:
18
Experience rustic charm in our "Big Montana" Log Cabin located at Elkhart Lodge. The Big Montana cabin, hosted by Shebo ...
From $742 per night (USD)
VRBO
From $333 per night (USD)
VRBO
Peaceful Retreat, Near Road America! Mid Century Modern Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Peaceful and private getaway in the woods, yet close to everything! Shops, restaurants, bars, parks, golf, fishing, sail ...
From $333 per night (USD)
VRBO
From $598 per night (USD)
VRBO
The Woods Estate - walk to Road America & near Kohler Golf ~ Modern Luxury
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Experience the beauty & comfort if this luxury contemporary home nestled in the woods on 5 acres walking distance to Ro ...
From $598 per night (USD)
VRBO
From $310 per night (USD)
VRBO
Sheboygan Getaway w/ Deck + On-Site Lake Access!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Plan for plenty of outdoor fun on your next Lake Michigan getaway when you stay at this Sheboygan vacation rental! With ...
From $310 per night (USD)
VRBO
From $220 per night (USD)
VRBO
Updated Plymouth Home ~ 5 Mi to Road America!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Get ready for an unforgettable getaway at this charming 3-bedroom, 1.5-bath vacation rental in Plymouth! Located just a ...
From $220 per night (USD)
VRBO
From $294 per night (USD)
VRBO
Centrally located house minutes away from the lake, golfing, & Road America.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Get cozy on the big covered front porch by enjoying a cup of coffee or a local brew. Relax with a book or glass of wine ...
From $294 per night (USD)
VRBO
From $119 per night (USD)
VRBO
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Place is all for you! No share place. Forget your worries in this spacious and serene Guest House ( sleeps 4 people) q ...
From $119 per night (USD)
VRBO
From $159 per night (USD)
Expedia
Sleeps 7{SPACIOUS}Pets Welcome!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $159 per night (USD)
Expedia
$LUX Uptown Escape - The Trester\n$
From $179 per night (USD)
VRBO
LUX Uptown Escape - The Trester\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our beautiful 2-bedroom historic home in Uptown Sheboygan! This charming and well-appointed residence offers ...
From $179 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Riverfront Townhome with Breathtaking Water Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
*exterior fire table cannot be used after october 1. Welcome to Driftwood, our modern two-bedroom, 1.5-bath townhome, n ...
From $205 per night (USD)
Expedia
From $148 per night (USD)
VRBO
Cozy Cape Cod Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy cape cod home behind the Plymouth racetrack, loud during race season. Close to Road America (8 min; 5.8 miles), nea ...
From $148 per night (USD)
VRBO
From $126 per night (USD)
VRBO
Cute Quiet Neighborhood Hideway
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Step back in time and relax in this 1930’s bungalow. Situated on the south side of the City of Sheboygan, able to feel t ...
From $126 per night (USD)
VRBO
From $742 per night (USD)
VRBO
Luxurious artistic 2 bed - 2 bath Condo; feel like living by the Coast!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This is a very well-taken care of condo in the most touristic part of Sheboygan. Be close to two beaches, a pier walk, a ...
From $742 per night (USD)
VRBO
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Expedia
Charming 4 bedroom 2 bath Sheboygan Falls
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
4 bedroom, 2 full bath Cape Cod home located in historic Sheboygan Falls, WI. 5 minuted from Kohler, 10 minute drive to ...
Click For Pricing
Expedia
From $222 per night (USD)
VRBO
The Cottage - Newly Renovated Beachfront Condo on Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
The Cottage by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. ...
From $222 per night (USD)
VRBO
From $1253 per night (USD)
Expedia
Summit Road Estate - Top Luxury
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Introducing the Summit Road Estate: Wisconsin's Epitome of Luxury This secluded hilltop palace redefines luxury living, ...
From $1253 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Enjoy your Sheboygan getaway in this spacious 4-bedroom, 2-bath home just a 5-minute walk to the lake. Sleeps 11 and pac ...
From $426 per night (USD)
VRBO
From $145 per night (USD)
VRBO
Lovely Lake Lookout - Cozy 2BR Condo Steps from Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Lovely Lake Lookout by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, ...
From $145 per night (USD)
VRBO
From $241 per night (USD)
VRBO
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in the heart of Sheboygan, our location is a true gem! We are just steps away from the shores of Lake Michigan a ...
From $241 per night (USD)
VRBO
$Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan\n$
From $1230 per night (USD)
Expedia
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan\n
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Escape to your own private Lakeside Retreat. 4 BR, 2.5 bath Cape Cod overlooking Lake Michigan & Black River giving you ...
From $1230 per night (USD)
Expedia
From $708 per night (USD)
VRBO
Stunning Lakefront Cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Our Lakefront Cottage is a relaxing escape for nature enthusiasts and those seeking a peaceful retreat. Our newly remode ...
From $708 per night (USD)
VRBO
From $234 per night (USD)
VRBO
Modern South Pier Condo on Sheboygan River!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Stay in luxury at this 2-bedroom, 2-bathroom vacation rental in Sheboygan, WI. Enjoy the convenience of a fully equipped ...
From $234 per night (USD)
VRBO
From $177 per night (USD)
VRBO
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
About this space: Renovated 1930's home located in the historic downtown district within walking distance of breathtakin ...
From $177 per night (USD)
VRBO
From $339 per night (USD)
Expedia
tranquil cabin on 5 private acres w/ hot tub and sauna
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming ...
From $339 per night (USD)
Expedia
From $191 per night (USD)
VRBO
Lovely Elkhart Lake Apartment - Walk to Town!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Move into an airy Wisconsin getaway for the weekend, where you can stroll to beautiful Elkhart Lake or fire up grills fo ...
From $191 per night (USD)
VRBO
Click For Pricing
Expedia
Spacious Blue Harbor 2 bedr courtyard view condo w/ Breaker Bay Waterpark access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Detach yourself from the main crowd and check yourself into the 1242 square feet of spacious privacy of your own lakesid ...
Click For Pricing
Expedia
From $1167 per night (USD)
VRBO
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Welcome to Fairway Getaway! This stunning property combines luxury, comfort, and convenience, making it the perfect choi ...
From $1167 per night (USD)
VRBO
From $152 per night (USD)
Expedia
LAKE HOUSE Relax'n in or on the water this is your place for memories to be made
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Kettle Moraine Long Lake Vacation Get Away. Comfort begins as you enter the door to your lake frontage studio style vaca ...
From $152 per night (USD)
Expedia
From $282 per night (USD)
VRBO
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Located in a quiet neighborhood surrounded by wildlife. Concrete patio is perfect for bonfires and family bonding. Too c ...
From $282 per night (USD)
VRBO
From $136 per night (USD)
VRBO
Cozy and private 3 bedroom unit located a few blocks from downtown Sheboygan.
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Located just a couple blocks from downtown Sheboygan! Visit the shops and unique restaurants just a short walk away, or ...
From $136 per night (USD)
VRBO
From $134 per night (USD)
VRBO
Urban Lake Condo in Sheboygan's Historic Ellis District
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Your family will be within walking distance of almost everything when you stay at this centrally-located harborside gem ...
From $134 per night (USD)
VRBO
From $262 per night (USD)
Expedia
Hidden Haven - Luxury Cottage w/ Hot Tub & Scenic Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hidden Haven by Great Lakes Getaways! Discover our new modern cottage on Lake Michigan’s coast, nestled on a spacious 3 ...
From $262 per night (USD)
Expedia
From $148 per night (USD)
VRBO
Dog-Friendly Sheboygan Home - 1 Mi to Town!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the best of Sheboygan with your loved one from this 1-bed, 1-bath vacation rental! This newly renovated home ...
From $148 per night (USD)
VRBO
From $255 per night (USD)
VRBO
Riverwalk Retreat - Riverfront 3BR Condo w/ Jacuzzi & Lake Michigan Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Riverwalk Retreat by Great lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2 ...
From $255 per night (USD)
VRBO
From $74 per night (USD)
VRBO
Lakeside Condo - 2BR, Lake Michigan Views & Massage Chair
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Crystal Cove by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. ...
From $74 per night (USD)
VRBO
$Camp Skywood - New Listing!\n\n$
From $533 per night (USD)
VRBO
Camp Skywood - New Listing!\n\n
Bedrooms:
2
Bathrooms:
4
Sleeps:
2
Just minutes away from Downtown Elkhart Lake, this custom built cordwood home is truly a tucked away sanctuary. The 16 s ...
From $533 per night (USD)
VRBO
From $373 per night (USD)
VRBO
Waterfront Condo, Private Beach, Outdoor/Indoor Pools, & Walkable to Downtown
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Make summer memories at Elkhart Lake! Only 3 bedroom, 3 bath, condo located steps from the beach. Fully renovated in 2 ...
From $373 per night (USD)
VRBO
From $262 per night (USD)
VRBO
Lighthouse Lookout - 3BR / Steps to Lake Michigan & Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lighthouse Lookout by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, ...
From $262 per night (USD)
VRBO
$\n\nLuxury Downtown Sheboygan 4BR-2.5 Bath - 3 min walk to beach - Lakeside Legacy$
From $766 per night (USD)
VRBO
\n\nLuxury Downtown Sheboygan 4BR-2.5 Bath - 3 min walk to beach - Lakeside Legacy
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Grand colonial meets coastal luxe in this 2800 square ft, 4 bedroom home along the magnificent Lake Michigan coast. Stun ...
From $766 per night (USD)
VRBO
From $552 per night (USD)
Expedia
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Luxury Modern Farmhouse 4B-2Ba Lake & Beach House! Is it time for a Cool Change? Relax and rejuvenate at Sheboygan's n ...
From $552 per night (USD)
Expedia
From $844 per night (USD)
VRBO
Family Home w/ Indoor Pool ~ 2 Mi to Elkhart Lake!
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
Endless family fun awaits at this pet-friendly, 5-bedroom, 4-bath vacation rental in Elkhart Lake, WI! This spacious hom ...
From $844 per night (USD)
VRBO
From $158 per night (USD)
Expedia
Downtown, Uniquely Designed, Near the Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to the Uptown Coach House, hosted by Sheboygan Vacation Rentals. Our newly built coach house is nestled in the ...
From $158 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $355 per night (USD)
Expedia
State Park w/ Orchard Style Yard & Pavilion
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to our Orchard House Retreat, hosted by Sheboygan Vacation Rentals. Our home is situated directly across from t ...
From $355 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Apartment near many locations.
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Premier View and Patio Overlooking Elkhart Lake! Two minute walk to bars/dining!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy listening to bands from the private large patio while overlooking Elkhart Lake and the pool. Updated nice furnish ...
Click For Pricing
VRBO
From $186 per night (USD)
VRBO
Cozy Corner Cottage- 2 blocks to Lake Michigan. Walk to Deland Park and Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Cozy Corner Cottage by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, ...
From $186 per night (USD)
VRBO
From $170 per night (USD)
VRBO
Centrally located apartment
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 $170 per night (USD)
VRBO
From $218 per night (USD)
VRBO
Cozy Elkhart Lake Apartment: Walk to Town & Dining
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Experience tranquility and serenity in this 2-bedroom, 1-bath vacation rental in Elkhart Lake, Wisconsin. This apartment ...
From $218 per night (USD)
VRBO
From $434 per night (USD)
VRBO
Boat in Sheboygan Harbor for Mercury Midwest Challenge!
Bedrooms:
0
Bathrooms:
2
Sleeps:
5
40' Yacht on Lake Michigan, slipped at the Sheboygan Yacht Club. Come live aboard a 40ft by 13ft boat with all the mode ...
From $434 per night (USD)
VRBO
From $421 per night (USD)
Expedia
Charming 3-bedroom 3 Bathroom house in Sheboygan with AC, WiFi, & Amenities
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy a peaceful stay at this cozy 3-bedroom, 3 living room, and 3 bathroom home in Sheboygan, WI. This charming propert ...
From $421 per night (USD)
Expedia
From $378 per night (USD)
VRBO
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Welcome to The Hemisphere House, a unique dome retreat in a charming Wisconsin neighborhood. This architectural gem offe ...
From $378 per night (USD)
VRBO
From $202 per night (USD)
VRBO
Lake & Trail Getaway - Perfect for a Fall getaway!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This A-frame cottage boasts 3 inviting bedrooms. The bedrooms will ensure a comfortable stay for all guests. The cozy a ...
From $202 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $269 per night (USD)
Expedia
Apartment near many locations.
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $269 per night (USD)
Expedia
From $269 per night (USD)
VRBO
Apartment near many locations.
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $269 per night (USD)
VRBO
From $269 per night (USD)
Expedia
Apartment near many locations.
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $269 per night (USD)
Expedia
From $269 per night (USD)
VRBO
Apartment near many locations.
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Only two laps from Road America, or 20 minutes from the beach, this secluded apartment complex is located on the peacefu ...
From $269 per night (USD)
VRBO
From $561 per night (USD)
Expedia
Executive Beachfront Villa: Sleeps 8!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Just steps from Lake Michigan, this updated 2BR/2BA condo features modern décor, new flooring, and refreshed showers for ...
From $561 per night (USD)
Expedia
From $263 per night (USD)
VRBO
Lakefront Condo- Step-free & accessible! Sleeps 8!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Enjoy the beauty of Lake Michigan just steps from your door in this 2BR/2BA beachfront condo. Located near the boardwalk ...
From $263 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Edgewater Villa: 4 Bedroom, Sleeps 14!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Modern 4BR Courtyard Condo – Steps from the Beach in the "Malibu of the Midwest" Escape to Sheboygan, WI—a hidden gem o ...
From $385 per night (USD)
Expedia
From $263 per night (USD)
VRBO
Beachfront Paradise: King Suite - Sleeps 8!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Soak in Lake Michigan views from this 2BR/2BA beachside condo, just steps from the boardwalk, harbor, shops, and restaur ...
From $263 per night (USD)
VRBO
From $588 per night (USD)
Expedia
Lakeside Cabin Retreat Relax at Private Lake House!
Bedrooms:
1
Bathrooms:
3
Sleeps:
11
Overview Immerse yourself in tranquility at Highlander Hideaway, a unique longhouse-style retreat nestled on 70+ acre pr ...
From $588 per night (USD)
Expedia
From $924 per night (USD)
VRBO
This house is a 5 bedroom(s), 4.5 bathrooms, located in Elkhart Lake, WI.
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
This 6810 sq ft, Brand New Construction (Not Remodeled) just completed July of 2024 boasts 5 Bedroom, 4.5 bathroom and ...
From $924 per night (USD)
VRBO
From $305 per night (USD)
VRBO
3 Mi to Road America: Spacious Elkhart Lake Home!
Bedrooms:
2
Bathrooms:
5
Sleeps:
13
Large Fenced Backyard | Walk to Shops & Restaurants | Gas Grill (Propane Provided) Experience all that Elkhart Lake has ...
From $305 per night (USD)
VRBO
From $181 per night (USD)
VRBO
Pet-Friendly Sheboygan Home: 4 Mi to Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Indulge in a fun-filled getaway when you stay at this 2-bed, 1-bath Wisconsin vacation rental! Boasting a colorful open ...
From $181 per night (USD)
VRBO
From $299 per night (USD)
Expedia
New King Park Beach Lookout Deluxe! 3BR Right at Lake!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to King Park Beach Lookout Deluxe! Experience the perfect family getaway with panoramic views of Lake Michigan, ...
From $299 per night (USD)
Expedia
From $528 per night (USD)
VRBO
Cozy Lakefront Escape: Perfect for Seasonal Getaways & Large Groups
Bedrooms:
1
Bathrooms:
5
Sleeps:
14
Nestled on the picturesque point of Random Lake, Wisconsin, our inviting and family-friendly lakehouse offers a perfect ...
From $528 per night (USD)
VRBO
From $340 per night (USD)
Expedia
Family friendly farmhouse near Cascade with AC- Enjoy a peaceful retreat!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Escape to the tranquility of country living at The Farmhouse on Mink Creek. Nestled on an acre surrounded by picturesque ...
From $340 per night (USD)
Expedia
From $589 per night (USD)
VRBO
Road America and Golf Retreat
Bedrooms:
2
Bathrooms:
4
Sleeps:
18
Escape to tranquility at our charming rental, nestled in serene woods, just down the road from Road America and premier ...
From $589 per night (USD)
VRBO
From $493 per night (USD)
VRBO
Charming 4-bedroom house with WiFi and AC in lovely Sheboygan
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Unwind in this fabulous 1970's home with modern upgrades. This spacious 3700 SF retreat features 4 bedrooms (3 queen, ...
From $493 per night (USD)
VRBO
From $236 per night (USD)
VRBO
Steps from Lake Michigan: North Point Place
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Conveniently located for adventure and relaxation along the lakeshore and beyond, this historic home is steps away from ...
From $236 per night (USD)
VRBO
From $420 per night (USD)
VRBO
Luxury Lake Front Villa: Sleeps 12!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Experience the ultimate in luxury at this exquisite 4 bedroom lakefront vacation rental on Lake Michigan, just minutes f ...
From $420 per night (USD)
VRBO
From $461 per night (USD)
VRBO
The Links! - Luxury Golf Retreat with Golf Simulator
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Get ready to relax in this 4-bedroom house in Sheboygan. This superb property features 2 king beds and 2 queen beds, per ...
From $461 per night (USD)
VRBO
$\nPlymouth Gem: Spacious Home with Bar, Game Room & Yard Near Road America$
From $664 per night (USD)
VRBO
\nPlymouth Gem: Spacious Home with Bar, Game Room & Yard Near Road America
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to your home away from home in charming Plymouth, Wisconsin. Just minutes from Road America, this spacious 4-bed ...
From $664 per night (USD)
VRBO
From $190 per night (USD)
VRBO
Elkhart Lake, WI home close to lake, downtown, and Road America racetrack
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to our cherished family home, nestled in the heart of a magical town that holds countless memories for us. We're ...
From $190 per night (USD)
VRBO
From $167 per night (USD)
VRBO
Breezy Beach - 75 Steps to Lake Michigan!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to 𝐁𝐫𝐞𝐞𝐳𝐲 𝐁𝐞𝐚𝐜𝐡 by 𝐆𝐫𝐞𝐚𝐭 𝐋𝐚𝐤𝐞𝐬 𝐆𝐞𝐭𝐚𝐰𝐚𝐲𝐬! Take advantage of FLEXIBLE MONTHLY RENTAL ...
From $167 per night (USD)
VRBO
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VRBO
Shoreline Sanctuary - 4BR Villa w/ Lake Views, Beach Access & Sunsets
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Shoreline Sanctuary by Great Lakes Getaways! This stunning 4-bedroom, 3-bathroom beachfront villa on Lake Michigan offe ...
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VRBO
From $87 per night (USD)
VRBO
Wandering Waves - Beachfront Lake Michigan Stay!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Wandering Waves by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 202 ...
From $87 per night (USD)
VRBO
From $141 per night (USD)
VRBO
NEW! Indigo Waters- Steps to the sand! Sleeps 7! Book today!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Indigo Waters by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. ...
From $141 per night (USD)
VRBO
From $476 per night (USD)
Expedia
Sleeps 8! 2 Full Bath with Kitchenette!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
WELCOME RACE FANS AND VACATIONERS!! The Victorian Inn is located along a picturesque freshwater lake and within walking ...
From $476 per night (USD)
Expedia
From $154 per night (USD)
VRBO
Sunset Vista 2br in Sheboygan
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
This cozy vacation rental is a perfect place to relax and enjoy a getaway! From its warm and inviting fireplace, with co ...
From $154 per night (USD)
VRBO
From $592 per night (USD)
Expedia
1 min from Road America and the Village of Elkhart Lake
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This amazing vacation lodge is the perfect getaway spot for families and friends. Nestled on a private lot, surround by ...
From $592 per night (USD)
Expedia
From $267 per night (USD)
VRBO
2br Townhome with View of Road America!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Indulge in the ultimate vacation experience just steps from the main entrance of Road America. This charming townhome of ...
From $267 per night (USD)
VRBO
From $426 per night (USD)
VRBO
Luxury Villa on Lake Michigan!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to the ideal place on Lake Michigan for a family beach getaway, wind surfing, fishing, bachelorette weekend, gol ...
From $426 per night (USD)
VRBO
From $653 per night (USD)
VRBO
Vacation Paradise: 4 Bedroom, Sleeps 14!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Enjoy life on the shores of Lake Michigan in this luxury, courtyard condo. This two-story, 4 bedroom/3 bathroom get-away ...
From $653 per night (USD)
VRBO
From $130 per night (USD)
Expedia
Charming 2-bedroom condo with WiFi, AC in quaint Sheboygan
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This fantastic condo in Sheboygan offers two bedrooms with queen beds, perfect for a relaxing getaway. With amenities li ...
From $130 per night (USD)
Expedia
From $1267 per night (USD)
VRBO
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
🏡 Welcome to Baronwood Oasis – The Ultimate Family Escape - Sleeps 16 This is your moment to be the hero of your fam ...
From $1267 per night (USD)
VRBO
From $1023 per night (USD)
Expedia
Blue Barn on the Green with Farm House near the shores of Lake Michigan
Bedrooms:
4
Bathrooms:
5
Sleeps:
18
Welcome to this charming farmhouse and event barn in Oostburg. Imagine your perfect countryside escape. Nestled on five ...
From $1023 per night (USD)
Expedia
From $151 per night (USD)
VRBO
Lake Breeze on 11th
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Sheboygan has lots to offer & our place is perfect for your homebase. The lakefront, Sunrise, End, & Vollrath park are j ...
From $151 per night (USD)
VRBO
From $371 per night (USD)
VRBO
NEW! Charming 3BR/2BA Lake House in the Woods of the desirable Black River area
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Your much-needed retreat begins at this large 3-bedroom house 300-feet from Lake Michigan. This wonderful property featu ...
From $371 per night (USD)
VRBO
From $199 per night (USD)
VRBO
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to the Coastal Comfort! Comfort: noun - a state of physical ease and freedom from pain or constraint Come in a ...
From $199 per night (USD)
VRBO
From $545 per night (USD)
VRBO
2 Mi to Road America: Pet-Friendly Duplex!
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Walk to Elkhart Lake | Next to Quit Qui Oc Golf Course Indulge in a mix of tranquility and fun at this 4-bedroom, 2-bat ...
From $545 per night (USD)
VRBO
From $198 per night (USD)
VRBO
Private Beach, Pools & Full-Kitchen
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Million-Dollar Views & Historic Charm – Private Condo along Elkhart Lake 🏊‍♂️ Indoor & outdoor pools 🌿 Expansive gree ...
From $198 per night (USD)
VRBO
From $163 per night (USD)
Expedia
Sheboygan Sunrise Beach Stay
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
*** STEPS AWAY FROM LAKE MICHIGAN*** Experience the vibrant energy from our stylish apartment with great views. Enjoy e ...
From $163 per night (USD)
Expedia
From $834 per night (USD)
VRBO
5 min from Road America. Great yard and plenty of parking
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
This enchanting house in Elkhart Lake offers 5 bedrooms, including 1 king bed and 4 queen beds. With 2 bathrooms featuri ...
From $834 per night (USD)
VRBO
From $142 per night (USD)
VRBO
Overlook Oasis - Lakeside Stay in Ellis District
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Overlook Oasis by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through Ap ...
From $142 per night (USD)
VRBO

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Results: 343 Rentals