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

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From $441 per night (USD)
VRBO
Beach front luxury spacious villa !
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Beach front luxury spacious condo! Beautiful remodeled four bedroom villa/condo overlooking Lake Michigan, well equippe ...
From $441 per night (USD)
VRBO
From $259 per night (USD)
Expedia
4 Bedroom Home on the River with Private River access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Take in the coastal vibes as you enjoy your stay at this Riverfront home. With private access to the river, kayaks to us ...
From $259 per night (USD)
Expedia
From $400 per night (USD)
VRBO
LUXE Manor with Modern, Elegant Vibes
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Modern chic blends with classic sophistication in this late 1800s Manor. Enjoy the expansive 4,500 square feet of elegan ...
From $400 per night (USD)
VRBO
From $371 per night (USD)
Expedia
Coastal Comfort & Golfers' Paradise in Sheboygan!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled in the heart of the Historic District of Sheboygan, this 3-bedroom, 2-bathroom home is your basecamp for Lake Mi ...
From $371 per night (USD)
Expedia
From $1223 per night (USD)
VRBO
Beautiful home - Great for Road America, golf outings, NFL Draft, or just R&R!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Beautiful home in a quiet neighborhood. Less than a minute from Road America, 10 minutes to Elkhart Lake. Enjoy the to ...
From $1223 per night (USD)
VRBO
From $723 per night (USD)
VRBO
Retreat to Crystal Lake
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Beautiful Home on Crystal Lake. 120 feet of lake frontage. Large front yard and patio allow you to enjoy the beautiful ...
From $723 per night (USD)
VRBO
From $906 per night (USD)
VRBO
Modern Lakeside House with Treehouse
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Welcome to Curtiss Castle! Ideal for large families, remote workers, lake lovers, and golf enthusiasts! This peaceful, w ...
From $906 per night (USD)
VRBO
From $1006 per night (USD)
Expedia
Outdoor Sauna | 6-BR's | Kohler-Andrae
Bedrooms:
3
Bathrooms:
6
Sleeps:
15
Welcome to the House at Wilson Shore hosted by Sheboygan Vacation Rentals. Escape to the serene beauty of this stunning ...
From $1006 per night (USD)
Expedia
From $451 per night (USD)
VRBO
Pristine Beach Access, Arcade near Kohler-Andrae
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to The Sandwood Cottage hosted by Sheboygan Vacation Rentals. Family and friends are everything. When we set ou ...
From $451 per night (USD)
VRBO
From $601 per night (USD)
Expedia
Elkhart Lake Oasis - 25 Acres, Hot Tub & Orchard - 15 Min to Road America
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Race weekend retreat on 25 quiet acres — soak under the stars in the hot tub, cook for the crew in a chef's kitchen, and ...
From $601 per night (USD)
Expedia
From $182 per night (USD)
VRBO
COMFY, COZY, and CONVENIENT!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Whether you are visiting for golf, fishing, a Green Bay Packer game, Road America, or simply a vacation, this convenient ...
From $182 per night (USD)
VRBO
From $373 per night (USD)
Expedia
Sleeps 8 & Spacious!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $373 per night (USD)
Expedia
From $337 per night (USD)
VRBO
Close to Downtown & Shore | Great Location
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $337 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Beautiful & Convenient!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $342 per night (USD)
Expedia
From $527 per night (USD)
VRBO
Wisconsin Vacation Rental: 1 Mi to Road America!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Bring the whole family along for a fun-filled vacation in Plymouth, Wisconsin! This unique vacation rental home near Roa ...
From $527 per night (USD)
VRBO
From $617 per night (USD)
VRBO
Racer’s Getaway - Rural, Upscale, Unique Home 8 minutes from Road America
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Our home is located on a very private 50 acre hobby farm in rural Elkhart Lake approximately 6 miles from Road America a ...
From $617 per night (USD)
VRBO
From $258 per night (USD)
VRBO
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to the Relax ‘n Retreat! Retreat: noun - a quiet or secluded place in which one can rest and relax Unwind at o ...
From $258 per night (USD)
VRBO
From $452 per night (USD)
VRBO
Close to Downtown Elkhart Lake!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located 7 blocks from Beautiful Clear Elkhart Lake. Summertime is a Great Time in Elkhart Lake with the Lake for swimmin ...
From $452 per night (USD)
VRBO
From $464 per night (USD)
VRBO
Beautifully Updated Two Queen Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
WELCOME RACE FANS AND VACATIONERS!!!! The Victorian Inn is the perfect lodging for families and friends. Located along a ...
From $464 per night (USD)
VRBO
From $239 per night (USD)
Expedia
Elegant Condo in Historic Sheboygan Falls, Licensed and inspected by Sheb County
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful Upper Condo in Historic Sheboygan Falls. Licensed and professionally inspected by Sheboygan County, next to th ...
From $239 per night (USD)
Expedia
From $339 per night (USD)
VRBO
Beach House on the shores of Lake Michigan Near downtown Sheboygan
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Amazing location on the shores of Lake Michigan. One of only a few homes in the city of Sheboygan that are right on the ...
From $339 per night (USD)
VRBO
From $439 per night (USD)
Expedia
Perfect Paradise | 4BR Lakeview Condo w/ Jacuzzi
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Perfect Paradise — Presented by Great Lakes Getaways! Unwind in this spacious 4-bedroom, 3-bath beachfron ...
From $439 per night (USD)
Expedia
From $637 per night (USD)
VRBO
Waterfront and Pool View Condo!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
WELCOME RACE FANS AND VACATIONERS!!!! The Lakeside Suites are located along a picturesque freshwater lake and within wal ...
From $637 per night (USD)
VRBO
From $824 per night (USD)
Expedia
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 $824 per night (USD)
Expedia
From $623 per night (USD)
VRBO
Walk to Road America & near Kohler Golf ~ The Woods Estate ~ Modern Luxury
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Experience the beauty & comfort if this luxury contemporary home nestled in the woods on 5 acres walking distance to Ro ...
From $623 per night (USD)
VRBO
From $378 per night (USD)
Expedia
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 $378 per night (USD)
Expedia
From $407 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 $407 per night (USD)
VRBO
Click For Pricing
Expedia
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Forget your worries in this spacious and serene Guest House Minutes from downtown Sheboygan/Kohler, a 5 star PGA champi ...
Click For Pricing
Expedia
From $327 per night (USD)
VRBO
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 $327 per night (USD)
VRBO
From $185 per night (USD)
Expedia
LUX Uptown Escape - The Trester
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 $185 per night (USD)
Expedia
From $304 per night (USD)
VRBO
The Cottage - Beachfront Condo on Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to The Cottage — Presented by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now ...
From $304 per night (USD)
VRBO
From $648 per night (USD)
Expedia
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 $648 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Lovely Lake Lookout - Cozy Condo Steps from Lake
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to Lovely Lake Lookout — Presented by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—avail ...
From $303 per night (USD)
VRBO
From $426 per night (USD)
Expedia
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 $426 per night (USD)
Expedia
From $765 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 $765 per night (USD)
VRBO
From $470 per night (USD)
Expedia
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 $470 per night (USD)
Expedia
From $271 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 $271 per night (USD)
VRBO
From $395 per night (USD)
Expedia
tranquil cabin on 5 private acres w/ hot tub and sauna
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for w ...
From $395 per night (USD)
Expedia
From $257 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 $257 per night (USD)
VRBO
From $128 per night (USD)
Expedia
Lakeview Loft - Just opened up for July!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Looking for extended stays? We offer monthly rates. Inquire within, or check out StayWithNSD Bright and cozy 2-bedroom, ...
From $128 per night (USD)
Expedia
From $1977 per night (USD)
VRBO
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
Bedrooms:
3
Bathrooms:
5
Sleeps:
15
Welcome to Fairway Getaway! This stunning property combines luxury, comfort, and convenience, making it the perfect choi ...
From $1977 per night (USD)
VRBO
From $212 per night (USD)
Expedia
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 $212 per night (USD)
Expedia
From $179 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 $179 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Beachside Condo Downtown with Lake Michigan Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You will see & hear the beauty of Lake Michigan during your stay at this main floor Waves of Happiness Condo hosted by S ...
From $234 per night (USD)
Expedia
From $214 per night (USD)
VRBO
Beachside Condo w/ Stunning Lake Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Blue water+White sand+Waves will surely make your stay in our second-floor Waves of Happiness Condo hosted by Sheboygan ...
From $214 per night (USD)
VRBO
From $193 per night (USD)
Expedia
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 $193 per night (USD)
Expedia
From $751 per night (USD)
VRBO
Large Farmhouse near RA & golf. Breakfast Included with lots of room for all!
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Discover Wirewalker Family Farm, a distinctive Bed and Breakfast nestled in the heart of Sheboygan County. Our recently ...
From $751 per night (USD)
VRBO
From $528 per night (USD)
VRBO
Camp Skywood - New Listing!
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Just minutes away from Downtown Elkhart Lake, this custom built cordwood home is truly a tucked away sanctuary. The 16 s ...
From $528 per night (USD)
VRBO
From $550 per night (USD)
VRBO
Waterfront Condo, Private Beach, Outdoor Pool & Hot Tub & 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 $550 per night (USD)
VRBO
From $915 per night (USD)
Expedia
Luxury Home Historic location 4BR-3 FullBath- Walk 3 min beach, 10 to downtown
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
✿ Welcome to Lakeside Legacy House, located in the historic district of Sheboygan. This spacious luxury home sits so ...
From $915 per night (USD)
Expedia
From $688 per night (USD)
VRBO
Luxury Lakeside Home-NEW Renovation-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 $688 per night (USD)
VRBO
From $903 per night (USD)
Expedia
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 $903 per night (USD)
Expedia
From $464 per night (USD)
VRBO
First Floor Pet Friendly Queen Suite with Single Pull-out
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
WELCOME RACE FANS AND VACATIONERS!!!! The Victorian Inn is located along a picturesque freshwater lake and within walkin ...
From $464 per night (USD)
VRBO
From $368 per night (USD)
Expedia
Beachside, Chefs Kitchen, High-End Everything
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our "Delightful Seaside Picnic," hosted by Rose and Fern and Sheboygan Vacation Rentals! This newly renovat ...
From $368 per night (USD)
Expedia
From $388 per night (USD)
VRBO
Road America, Elkhart Lake!
Bedrooms:
2
Bathrooms:
5
Sleeps:
7
Summary: Come enjoy this peaceful home just outside of Elkhart lake, about 5 mins. Whether its your whole family, Race T ...
From $388 per night (USD)
VRBO
From $216 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 $216 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Cozy Corner Cottage| Beach Access & Historic Charm
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Welcome to Cozy Corner Cottage — Presented by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—avail ...
From $362 per night (USD)
VRBO
From $289 per night (USD)
Expedia
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 $289 per night (USD)
Expedia
From $849 per night (USD)
VRBO
Farm Fresh Eggs, Amazing Outdoor Space w/ Fire Pit
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
ESCAPE THE ORDINARY AT THIS ONE-OF-A-KIND, HISTORIC PROPERTY, Old Trees Farm, hosted by Sheboygan Vacation Rentals. You ...
From $849 per night (USD)
VRBO
From $632 per night (USD)
Expedia
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 $632 per night (USD)
Expedia
From $355 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 $355 per night (USD)
VRBO
From $355 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 $355 per night (USD)
Expedia
From $355 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 $355 per night (USD)
VRBO
From $355 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 $355 per night (USD)
Expedia
From $827 per night (USD)
VRBO
Edgewater Villa: 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 $827 per night (USD)
VRBO
From $457 per night (USD)
Expedia
Beachfront Paradise: King Suite - Sleeps 8!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Wake up to stunning lake views in this bright and airy two-bedroom, two-bathroom beachfront condo. The open living space ...
From $457 per night (USD)
Expedia
From $361 per night (USD)
VRBO
Lakeside Cabin on Private Lake! Perfect for families and couples getaway.
Bedrooms:
1
Bathrooms:
3
Sleeps:
11
Escape to Your Own Private Wilderness One of the things guests love most is that they never have to leave the property. ...
From $361 per night (USD)
VRBO
From $1245 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 $1245 per night (USD)
VRBO
From $822 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 $822 per night (USD)
VRBO
From $366 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 $366 per night (USD)
Expedia
From $725 per night (USD)
VRBO
Lakeside Haven - New Deck, Pier & Guest House
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 $725 per night (USD)
VRBO
From $419 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 $419 per night (USD)
Expedia
From $641 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 $641 per night (USD)
VRBO
From $316 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 $316 per night (USD)
VRBO
From $657 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 $657 per night (USD)
VRBO
From $612 per night (USD)
Expedia
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 $612 per night (USD)
Expedia
From $273 per night (USD)
VRBO
On the Water in Sheboygan River Overlook
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The views from inside make it feel as if the home is overhanging the beautiful Sheboygan River. Go kayaking, enjoy the ...
From $273 per night (USD)
VRBO
From $964 per night (USD)
VRBO
Plymouth Gem: Spacious Home with Bar, Game Room & Yard Near Road America
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to your home away from home in charming Plymouth, Wisconsin. Just minutes from Road America, this spacious 4-bed ...
From $964 per night (USD)
VRBO
From $194 per night (USD)
VRBO
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to the Beachy Bungalow! Come in and unwind at our beachy 3 bedroom upper unit near Lake Michigan, Whistling Str ...
From $194 per night (USD)
VRBO
From $602 per night (USD)
Expedia
The 2,400 sq. ft. Plymouth Paddock near Road America, 4 bedrooms, 2.5 bathrooms
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This charming two story, 2400 square ft colonial house is the perfect respite for families looking to connect, or race ...
From $602 per night (USD)
Expedia
From $237 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 $237 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Breezy Beach | Villa 75 Steps from Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Welcome to Breezy Beach — Presented by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available no ...
From $314 per night (USD)
Expedia
From $502 per night (USD)
VRBO
Shoreline Sanctuary | Family Beach Villa with Deck
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to Shoreline Sanctuary — Presented by Great Lakes Getaways! This stunning 4-bedroom, 3-bathroom beachfront v ...
From $502 per night (USD)
VRBO
From $355 per night (USD)
Expedia
Indigo Waters - Steps to the sand! 2BR | Sleeps 7!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Welcome to Indigo Waters — Presented by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available n ...
From $355 per night (USD)
Expedia
From $549 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 $549 per night (USD)
VRBO
From $819 per night (USD)
Expedia
Vacation Paradise: 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 $819 per night (USD)
Expedia
From $241 per night (USD)
VRBO
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 $241 per night (USD)
VRBO
From $1479 per night (USD)
Expedia
Baronwood Oasis | Pool + Arcade Mega Estate
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Baronwood Oasis is a 10,500-sq-ft private all-season resort on six wooded acres—built for family reunions, golf trips an ...
From $1479 per night (USD)
Expedia
From $189 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 $189 per night (USD)
VRBO
From $491 per night (USD)
Expedia
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 $491 per night (USD)
Expedia
From $220 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 $220 per night (USD)
VRBO
From $213 per night (USD)
Expedia
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to the Getaway! Getaway: noun - an act or instance of getting away; a place suitable for a vacation You will u ...
From $213 per night (USD)
Expedia
From $392 per night (USD)
VRBO
Black River Retreat Eclectic-Unique-Intriguing
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Wow. An amazing home in an amazing location. Minutes from downtown Sheboygan, beaches at Kohler Andre & Lakeview parks, ...
From $392 per night (USD)
VRBO
From $765 per night (USD)
Expedia
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 $765 per night (USD)
Expedia
From $216 per night (USD)
VRBO
Private Beach, Pool & Full-Kitchen
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Million-Dollar Views & Historic Charm – Private Condo along Elkhart Lake 🏊‍♂️ Outdoor pool 🌿 Expansive green spaces � ...
From $216 per night (USD)
VRBO
From $239 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 $239 per night (USD)
Expedia
From $1145 per night (USD)
VRBO
5 min from Road America. Great yard and plenty of parking
Bedrooms:
2
Bathrooms:
5
Sleeps:
15
This enchanting house in Elkhart Lake offers 5 bedrooms, including 1 king bed and 4 queen beds. With 2 bathrooms featuri ...
From $1145 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Overlook Oasis | Coastal Haven in Ellis District
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Overlook Oasis — Presented by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available ...
From $243 per night (USD)
Expedia
From $174 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 $174 per night (USD)
VRBO
From $1692 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 $1692 per night (USD)
VRBO

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Results: 297 Rentals