Vacation Home Rentals By Owner In Sheboygan, WI

$254.72

Coastal Comfort & Golfers' Paradise in Sheboygan!

Sheboygan, Wisconsin, United States

Nestled in the heart of the Historic District of Sheboygan, this 3-bedroom, 2-bathroom home is your basecamp for Lake Michigan and world-class golf. Catch a sunrise at the beach or tackle the greens at Whistling Straits — everything is within reach. Whether you’re here for a weekend of legendary fairways or just to enjoy the fresh lake air, this retreat puts the best of the city right at your doorstep. Grab your clubs and see why Sheboygan is the ultimate lakeside escape!brbr-- THE PROPERTY --brbr- Primary Suite: Features a comfortable king-sized bedbr- Guest Rooms: Two additional bedrooms each feature a queen-sized bedbr- Fully Equipped: Full kitchen, in-home washer/dryer, high-speed Wi-Fi, and a Smart TVbr- Entertainment: Unwind with tons of board games for a cozy night inbr- Total Comfort: Climate-controlled with AC and central heatingbr- Parking: Private driveway for easy, off-street parkingbr- Grill: Fire up the outdoor grill for a post-golf BBQbrbr-- THE LOCATION --brbr- Walkable: A short stroll to the Lake, and restaurants and shops of downtown Sheboyganbr- World-class golf is waiting at Whistling Straits, Black Wolf Run, and others, all nearby!brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- Dog friendly w/ $50 fee (+ taxes & fees, max 2)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This 2-story home requires exterior uneven stairs to enter (with a handrail on 1 side) and an additional interior staircase to access all bedrooms on the 2nd floor

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Select Dates for Price

Private Vacation Home

Riverfront Sheboygan Townhome w/ Grill!

Sheboygan, Wisconsin, United States

Find rest and relaxation where the Sheboygan River flows into Lake Michigan at this 2-bedroom, 1.5-bathroom townhome. This 2-story Sheboygan vacation rental is the perfect place to spend time on the water, with on-site river access and proximity to beaches lining the shores of the lake close by. Take the kayak and paddleboard out for a peaceful ride, stroll the boardwalk through the sand dunes and golden beach of Kohler-Andrae State Park, or walk downtown to explore the museums and nightlife.brbr-- THE PROPERTY --brbrFurnished Balcony | Gas Grill | Kayak & Paddle Board | 1,200 Sq FtbrbrBedroom 1: King Bed | Bedroom 2: King Bed, Queen Murphy Bed | Living Room: Sleeper Sofa | Additional Sleeping: Queen Air Mattress, Pack ‘n PlaybrbrINDOOR LIVING: Smart TVs w/ cable, Amazon Alexa, board games, breakfast bar w/ seatingbrOUTDOOR LIVING: Bicycles w/ helmets, beach chairs, beach towels & blanket, beach cart, cooler, outdoor gamesbrBABY SUPPLIES: High chair, bath seat, swing, sound machinesbrKITCHEN: Cooking basics, cooking spices, dishware/flatware, dishwasher, refrigerator, stove, microwave, cooler, coffee maker, K-cups, tea, blender, Instant Pot, air fryer, toaster, ice maker, garbage disposalbrGENERAL: Free WiFi (500 Mbps), keyless entry, central heating & air conditioning, ceiling fans, complimentary toiletries, linens/towels, washer/dryer, laundry detergent, clothes steamer, iron/board, hangers, hair dryer, hair straightener, sharps container, trash bags/paper towelsbrSUITABILITY: Stairs required for access, 2-story townhomebrPARKING: Street parking (first-come, first-served)brbr-- THE LOCATION --brbrOUTDOOR ADVENTURE: Kiwanis Park (0.7 miles), Bookworm Gardens (2.7 miles), Maywood (3.3 miles), Kohler-Andrae State Park (6.7 miles), Whistling Straits Golf Course (6.9 miles)brON THE WATER: River access (on-site), Deland Park (1.4 miles), Harbor Centre Marina (1.5 miles), Blue Harbor Resort & Water Park (1.5 miles), South Shore Beach (1.8 miles)brNEARBY FUN: Above & Beyond Children's Museum (0.9 miles), John Michael Kohler Arts Center (1.0 miles), Kohler Design Center (4.4 miles), Odyssey Fun Center (5.8 miles), Elkhart Lake's Road America (16.9 miles) brAIRPORT: General Mitchell International Airport (65.9 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to access

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$595.88

/ Nightly

Private Vacation Home

4- Bedroom Retreat with Sauna, Game Room, Patio & Walk to Bars & Restaurants

Sheboygan, Wisconsin, United States

This newly renovated home offers the ultimate blend of comfort, fun, and convenience. Located in the heart of the city, you’ll be just steps away from the area’s best restaurants, bars, coffee shops, and nightlife. brbrInside, enjoy a spacious area ideal for relaxing or entertaining. Each bedroom has its own smart TV. Challenge your friends or family in the fully equipped game room, featuring a pool table, air hockey, and more. After a day exploring the city, unwind in your private 2 person sauna.brbrbrStep outdoor to enjoy a spacious 20 foot gazebo with dinning room seating and a sectional couch, a charcoal grill for outdoor cooking and a brand new fire pit with cozy seating- perfect for summer nights. But that’s not all: the backyard offers direct access to a park with a basketball court, giving kids even more to love.

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$378.83

/ Nightly

Private Vacation Home

BEACHVIEW GETAWAY

Sheboygan, Wisconsin, United States

Amazing location just off of Lake Michigan. A quick walk to the public beach across the street or downtown as well. Previous owner was an architect and owned the home for 60 years before he decided to downsize. Over 2200 square feet of living space. All FIVE bedrooms and a full bath are upstairs. There is a half bath on the main floor. The full bath upstairs has a stand-alone shower and a new whirlpool tub. Three bedrooms have queen size beds and TV's. Two smaller bedrooms each have a twin size bed. A queen size air mattress can be set up in on the first floor when needed with prior notice. There is a laundry room just off of the kitchen. There is a half bath on the main floor.brPlenty of room for the whole family. Perfect for a golfing weekend., family trip or girls' weekend. There is a gas grill out back. No smoking is allowed in the house. No parties or events are allowed on the property. Due to allergies, no pets are allowed. Minutes away from shopping and several golf courses around town. The interior of the home has just been repainted and new flooring put in. There is a 65 TV in the living room. WIFI access and cable TV present. Plenty of street parking along with a large two car garage at the back of the property. Check in time is 4pm or later and check out time is by 10am. There is a keypad on the front door for easy check in. I will provide the code two days before your arrival.

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$401.79

/ Nightly

Private Vacation Home

New King Park Beach Lookout Deluxe! 3BR Right at Lake!

Sheboygan, Wisconsin, United States

Welcome to King Park Beach Lookout Deluxe!brbrExperience the perfect family getaway with panoramic views of Lake Michigan, where comfort and convenience meet. The property is on a large corner lot directly across from a beautiful public beach and playground, offering unbeatable beach access and opportunities for sunrise walks. The open-concept living, dining, and kitchen areas feature expansive windows, keeping you connected to the lake throughout the day, regardless of season or weather. A favorite feature is the finished garage space that offers amenities such as a TV, a foosball table, a dining table, furnishings, and a mosquito net entrance. This space acts as a three-season room with great lake views and creates an ideal setting for family play, relaxation, or movie nights (Available May 1- October 31).brbrThis home features two bathrooms, two main-level bedrooms, and a spacious upstairs bunk room, perfect for guests of all ages with room for sleepovers, games, or simply hanging out. The fully equipped kitchen includes modern appliances and ample counter space, ideal for preparing meals or enjoying takeout. The dining table offers stunning lake views, while the sofa table provides additional seating. For comfort, the home offers central air with an extra room air conditioner to keep the upstairs cool. Enjoy high-speed internet and LIVE TV with Roku in the living area, king bedroom, and upstairs bunk room. Off-street parking plus a full-sized washer and dryer in the basement are available for guest use.brbrThe Beach Lookout Deluxe is the perfect starting point for exploring a variety of local attractions. Just a short distance away, you'll find the South Pier, charming downtown Sheboygan with its unique shops and restaurants, and the scenic village of Kohler. Whether you're teeing off at world-class golf courses, unwinding at the luxurious Kohler water spa, or heading to Elkhart Lake for thrilling racing at Road America, there's something for everyone. Outdoor enthusiasts will love the nearby waterfront, offering opportunities for charter fishing, kayaking, sailing, kiteboarding, and some of the best surfing in the Midwest. For a peaceful retreat, visit Kohler-Andrea State Park to explore sand dunes and marshlands. Don’t compromise between lake views and proximity to the beach, have it all at the Beach Lookout Deluxe. Reserve your dates now and start planning your perfect escape!br

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$496.0

/ Nightly

Private Vacation Home

LUXE Manor with Modern, Elegant Vibes

Sheboygan, Wisconsin, United States

Modern chic blends with classic sophistication in this late 1800s Manor. Enjoy the expansive 4,500 square feet of elegance and character that adorns this well-appointed home. Complete with 4 bedrooms, 3 full baths, and 1 half bath, many different areas for entertainment throughout, plus a designer patio. The neighborhood is of the most elite in Sheboygan, situated between the lakefront and downtown. Just a short drive to Whistling Straights and within an hour of Milwaukee and Green Bay.brbrTravel Time:br50 minutes to Milwaukeebr60 minutes to Green Baybr15 minutes to Whistling Straightsbr20 minutes to Elkhart Lakebr10 minutes to Kohler Water Spabr2 minutes from the Lakefrontbr2 minutes from Downtown SheboyganbrbrWelcome to the Wayne Charles Manor.brThe modern touches and stylish furniture throughout each room complement the original character of the manor which has been preserved throughout the years. The home features two wood-burning fireplaces, one in the great room and another in the den; nicknamed the green room. The great room also boasts an expansive wall of windows overlooking the manicured yard with a patio area and a garden pond which is frequented by mallards.brbrEnjoy every detail of the fine craftsmanship; stained glass windows, hardwood floors, original light fixtures, crown molding, and rich woodwork.brbrThe parlor features a baby grand piano and soaks in the sunlight almost all day long. Enjoy a formal dinner in the dining room featuring a built-in bar, rich woodwork, and stained glass windows.brbrThe eat-in kitchen is full of sunshine and is the perfect place to cook an evening dinner or enjoy a morning cup of coffee.brbrPatio season is everything and the bar is set high! Despite being located just a few minutes from Downtown and the lakefront, the Manor sits on a lot of just over half an acre. Mature trees, a garden pond, a grilling area, a designer patio, and a beautifully manicured lawn add to the charm of this mini-mansion. You are guaranteed to see an array of bird species, mallards, and rabbits! Firewood is provided should you want to have an outdoor fire.br

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$945.83

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Private Vacation Home

Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan

Sheboygan, Wisconsin, United States

Escape to your own private Lakeside Retreat. 4 BR, 2.5 bath Cape Cod overlooking Lake Michigan & Black River giving you the ultimate in privacy & serenity. Enjoy the view year-round from the 4-season sunroom. There are two 1st floor BRs. Upper primary suite offering a walk-in shower, fireplace, huge walk-in closet & patio doors to large upper deck with magnificent lake views! 2 car garage. Sunrises over Lake Michigan & sunsets over the Black River. Currently, there is no direct access to the water.

4

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2

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12

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$383.57

/ Nightly

Private Vacation Home

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Sheboygan, Wisconsin, United States

Nestled in the heart of Sheboygan, our location is a true gem! We are just steps away from the shores of Lake Michigan and an easy stroll to all that the downtown has to offer. brbrWe have 3 bedrooms with plenty of room to spread out. We are a sucker for a good theme so in the two downstairs bedrooms you will find small nods to our love for golf and cheese. One bathroom and laundry located on the main floor. Upstairs you will find another bedroom/loft and private bathroom. There is also a desk and kids corner where we hope they will have hours of fun. brbrOther Features: br- Fully equipped kitchen with modern appliances for all your cooking needs. - - Staples like salt& pepper, oil and basic seasonings provided. br-Keurig and Regular coffee pot with fully stocked coffee bar. Even a small coffee pot in the upstairs bedroom perfect for those lazy morningsbr-Gas fireplace br-Bottomless popcorn for movie nights br- Wi-Fi and Smart TV's giving you access to all your favorite streaming channelsbr-Spacious private backyard. br-Board Games, puzzles and books sure to entertain for hours br- Pack & Play, High Chair, kids plates/bowls/cups, baby gate at the top of the stairs, Kids Toys br- Grill and Outdoor Seating br- Lawn Games & Foosball Table br- Beach Towels, Chair, Toys and Cooler provided br-15 minute drive to Whistling Straights and Black Wolf Run br-20 minute drive to Kohler-Andrae State Park br-Many parks within walking distance (including historic Deland Park)br-Farmers Market every Saturday in the warmer months. Within a 1 minute walk from the house br-Easy walk to downtown shops and restaurants

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$291.52

/ Nightly

Private Vacation Home

Pet-Friendly 3BR Retreat!

Sheboygan, Wisconsin, United States

Relaxing 3-Bedroom Retreat Near Lake Michigan – Pet Friendly!brbrWelcome to your perfect home base in Sheboygan! This spacious 3-bedroom, 1-sofa bed, 1-bath, and basement with laundry, some weights, and pool table to offer comfort and convenience for your next getaway. Enjoy a full kitchen, a pool table for some fun, and the ease of having your own washer and dryer during your stay.brbrStep outside to a fully fenced backyard — great for pets — and fire up the Weber grill for a backyard BBQ.brbrYou’ll be just 5 miles from beautiful Lake Michigan and only 25 minutes from the excitement of Road America. Love the outdoors Explore nearby hiking spots like Kohler-Andrae State Park and the Ice Age Trail.brbrGolfers and spa-goers will love being close to Destination Kohler, home to Whistling Straits, Blackwolf Run, and the luxurious Kohler Waters Spa.brbrLocated halfway between Milwaukee and Green Bay, you’re in the perfect spot to explore everything the area has to offer.brbrAnd don’t miss some of my favorite local spots — grab breakfast or lunch at Field to Fork, or enjoy an evening out at Urbane Restaurant and Cocktail Bar on 8th Street in downtown Sheboygan.brbrWe’d love to host you — come relax, explore, and feel right at home!

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$911.38

/ Nightly

Private Vacation Home

Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub

Sheboygan, Wisconsin, United States

Escape to Sheboygan Chalet—a stunning modern retreat tucked in the woods of the Black River community Just two blocks from Lake Michigan and a short walk to Majerle’s Supper Club, this home blends style, comfort, and endless entertainment.brbrHighlights include:brbr4 spacious bedrooms, sleeps 10+brChef’s kitchen with quartz island ️brHot tub, infrared sauna & fire table brEpic game room with arcades, PS5 & ping pong brPeaceful wooded views from two decksbrbrThe perfect year-round getaway!brbrWelcome to Sheboygan Chalet | Game Room • Hot Tub • Sauna • Walk to Supper Club & LakebrbrWhether you`re planning a cozy fall retreat , a snowy winter weekend ❄️, or a summer adventure by the lake , Sheboygan Chalet offers the perfect year-round escape in one of Wisconsin’s most sought-after neighborhoods—Black River. Recently renovated from top to bottom, this peaceful wooded home is just two blocks from Lake Michigan and a short stroll to Majerle’s, a classic Wisconsin supper club . Designed with comfort, entertainment, and style in mind, Sheboygan Chalet is ideal for families, friends, and memory-making getaways.brbrbrbrBedrooms & Sleeping Arrangements ️brbrThis home offers three levels of space, comfortably sleeping up to 12 guests:brbrPrimary Bedroom (Upper Level): King bed, ensuite bathroom with a relaxing steam shower , and private access to a bonus bedroombrbrBonus Bedroom (Upper Level): Three twin beds – perfect for kids brbrBedroom 2 (Upper Level): Queen-over-Queen bunk bed with shared full hallway bathroombrbrBedroom 3 (Main Level): Queen bed with adjacent full bathroombrbrLower Level Rec Room: Queen pull-out couch for flexible sleeping space ️brbrFresh linens and cozy bedding are provided throughout.brbrbrbrbrKitchen, Dining & Living Spaces ️brbrThe open-concept layout is filled with natural light thanks to cathedral ceilings, skylights, and expansive windows overlooking the pines brbrFully equipped chef’s kitchen with quartz island, stainless steel appliances, and everything you need to cookbrbrDining room with access to one of two large decksbrbrLiving room with forest views, perfect for gathering or relaxingbrbrbrbrbrEntertainment for All Ages brbrThere`s something for everyone at Sheboygan Chalet:brbrGame Room (converted 32x24 garage):brbrMotorcycle racing arcade machines ️brbrKids climbing walls brbrPing pong table brbrCard table with games ♠️brbrPlayStation 5 with Smart TV brbrLower-level lounge with bar and chill-out space brbrHigh-speed WiFi and smart TVs for streaming brbrbrbrbrOutdoor Amenities brbrUnwind and enjoy the natural beauty that surrounds the home:brbrHot tub with peaceful forest backdrop brbrInfrared sauna for spa-like relaxation brbrFire table for evening conversations and s’mores brbrTwo expansive decks for lounging or diningbrbrWeber Genesis propane grill for outdoor cooking brbrbrbrbrLocation Highlights brbrLocated in Sheboygan`s tranquil Black River community, the home is close to everything while feeling worlds away:brbrTwo blocks from Lake Michigan access brbrShort walk to Majerle’s Supper Club for cocktails and classic Wisconsin fare brbr10 minutes to downtown Sheboygan, the marina, beach, and shops ️brbrNearby hiking trails, golf courses, and year-round recreation ‍♂️ ️brbrbrbrbrGuest Experience ✨brbrAt Sheboygan Chalet, we’ve thought through every detail so you can focus on making memories. From early morning coffee on the deck ☕ to late-night arcade competitions and everything in between, this home offers the perfect blend of relaxation and fun. Our team is committed to cleanliness, comfort, and top-tier hospitality throughout your stay.brbrbrbrbr Elevate Your Stay with VIP ExperiencesbrbrWisconsin Getaways offers exclusive concierge services to make your trip unforgettable:br- Private chefs for in-home gourmet dining.br- On-site massage therapists for ultimate relaxation.br- Custom-curated experiences for your group.brbrYour escape to the woods, the lake, and everything in between starts here. Book your stay at Sheboygan Chalet today and experience the best of Wisconsin’s hidden gem brbr Important — Guest Verification Required After BookingbrbrTo ensure a smooth and secure stay, all reservations complete a quick post-booking verification directly with Wisconsin Getaways. This secure step is completed outside of the platform and includes:brbr Providing a valid driver’s license or government-issued ID for the primary guestbr✍️ Signing our standard rental agreement directly with the HostbrbrThese items simply reaffirm the house rules shown here and do not override Airbnb or Vrbo’s Terms. Once completed, you’ll receive your arrival instructions—property address, parking details, and door codes—typically two weeks before check-in.brbr Quiet Community SettingbrbrMany of our homes are located in peaceful lakefront and residential neighborhoods. Guests love the tranquility, and we ask everyone to be mindful of neighbors and keep outdoor noise low, especially in the evenings. This helps maintain the relaxing atmosphere our properties are known for.brbr House Standards (Must Be Followed)brbrTo keep our homes and communities in excellent condition, the following expectations are firmly enforced:brbr Stay within posted occupancy limitsbr Maintain respectful noise levelsbr No external speakers or outdoor music of any kindbr No unauthorized gatherings or eventsbr No indoor smoking ($600 violation)br Guests may bring a total of up to 4 vehicles. When a garage is available, it must be used to help limit the number of cars in the driveway. Absolutely no street parking is allowed at any time.brbrThese guidelines ensure every guest enjoys the high-quality, peaceful experience Wisconsin Getaways is known for.brbrIn alignment with our ongoing commitment to guest safety and comfort, this property has been inspected and approved as a lodging establishment by the Wisconsin Department of Agriculture, Trade and Consumer Protection. brbrFollow @WisconsinGetaways for updates, specials, and new property launches.br Important — Guest Verification Required After BookingbrbrTo ensure a smooth and secure stay, all reservations complete a quick post-booking verification directly with Wisconsin Getaways. This secure step is completed outside of the platform and includes:brbr Providing a valid driver’s license or government-issued ID for the primary guestbr✍️ Signing our standard rental agreement directly with the HostbrbrThese items simply reaffirm the house rules shown here and do not override Airbnb or Vrbo’s Terms. Once completed, you’ll receive your arrival instructions—property address, parking details, and door codes—typically two weeks before check-in.brbr Quiet Community SettingbrbrMany of our homes are located in peaceful lakefront and residential neighborhoods. Guests love the tranquility, and we ask everyone to be mindful of neighbors and keep outdoor noise low, especially in the evenings. This helps maintain the relaxing atmosphere our properties are known for.brbr House Standards (Must Be Followed)brbrTo keep our homes and communities in excellent condition, the following expectations are firmly enforced:brbr Stay within posted occupancy limits (including visitors)br Maintain respectful noise levels (neighbors should not hear yelling or cursing at any time)br No outdoor speakers or amplified music (leave your speakers at home)br No unauthorized gatherings or eventsbr No indoor smoking ($600 violation)br Guests may bring a total of up to 4 vehicles. When a garage is available, it must be used to help limit the number of cars in the driveway. Absolutely no street parking is allowed at any time.brbrThese guidelines ensure every guest enjoys the high-quality, peaceful experience Wisconsin Getaways is known for.

3

Bath

13

Sleeps

Exceptional(3)

$810.72

/ Nightly

Private Vacation Home

Central located. Seconds from the highway to get to kohler, and Elkhart lake

Sheboygan, Wisconsin, United States

Everything you need on one level. complete modern Open concept living room, kitchen and dinning area. Hosts two large kitchen islands and bar/tv entertainment area and additional coffee bar. Step out to the Patio and relax with electric concrete fire table. Basement has full bath and additional recreation room. And extra large bedroom.

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$1031.08

/ Nightly

Private Vacation Home

Modern Lakeside House with Treehouse

Sheboygan, Wisconsin, United States

Welcome to Curtiss Castle! Ideal for large families, remote workers, lake lovers, and golf enthusiasts! This peaceful, woodsy retreat is steps from Lake Michigan. Room enough for the whole family to spread out and relax with a lake breeze!brbrSteps from a semi-private Lake Michigan beachbrbrEnjoy easy access to swimming, sunbathing, and beautiful sunrises without the crowds of a large public beach.brbrExceptional family-friendly amenities including a furnished treehousebrbrKeep guests of all ages entertained with unique features like a treehouse with a gaming console, a PACMAN arcade, and a backyard fire pit.brbrSpacious multi-level home designed for groupsbrbrComfortably accommodate your entire group with multiple living areas, a fully-equipped gourmet kitchen, and an expansive deck for gathering.br brNestled in the highly adored and well-preserved Black River neighborhood of Sheboygan, Wisconsin, near the picturesque shore of Lake Michigan, this home offers the feel of a Northwoods retreat while conveniently located between Green Bay and Milwaukee. This family-friendly home is just steps away from a semi-private beach and mere minutes from Kohler Andrae State Park, Road America, Kohler Waters Spa, and several exceptional golf courses.brbrBEDROOMS & BATHROOMSbrBedding, pillows, towel sets, body wash, hand soap, shampoo, conditioner, and hair dryers are provided.brbrPrimary Bedroom (top floor): King bed with plush topper, hardwood floor, electric fireplace, Smart TV, dresser, expansive walk-in closet with built-in drawers, dressing mirror, portable floor fan, luggage rack, and essential oil diffuser. The ensuite bathroom features Kohler shower fixtures, dual sinks with lighted mirrors, and a toilet with a bidet. brbrGuest Bedroom 1 (top floor): 1 Queen and 1 Twin bed, hardwood floor, 2 closets, open shelves with cube baskets for storage, nightstand, ceiling fan, and dressing mirror.brbrGuest Bedroom 2 (top floor): 1 Queen bed, hardwood floor, chest of drawers, two nightstands with charging ports, desk and chair, portable fan, closet, and dressing mirror. brbrThe guest bathroom on the top floor offers a relaxing soaking bathtub/shower, toilet, and dual sinks. brbrGuest Bedroom 3 (lower level): Two full-size beds with charging ports and LED-lighted shelves in the upholstered headboards, two nightstands and lamps, carpet, recessed lighting, luggage racks, closet, and dressing mirror. brbrThere is a 3/4 bathroom with a shower, toilet, and sink on this level.brbrTwo twin cots are also available in the den area and two pack-n-plays for our youngest guests.brbrMOVIE ROOM/DENbrThe spacious den is perfect for relaxation or family fun with a massive flat-screen TV, powered reclining sofas, electric fireplace, a mini fridge and microwave, cabinets full of board games and family-friendly DVDs, plus a classic PACMAN arcade!brbrKITCHENbrThe gourmet kitchen is equipped with an array of appliances to cater to your cooking and baking needs, including:br-large capacity refrigerator with ice and water dispenser, and a second refrigerator/freezer in the garage so you can stock up on your favorite Wisconsin beverages, cheeses, and frozen custard!br-double ovenbr-dishwasherbr -smooth-top cooking rangebr-air fryerbr-microwavebr-countertop stand mixerbr-spacious pantrybr-pots, pans, dishes, serving ware, & bakewarebr-kids' baking cabinet with cookie cutters and other fun stuffbr-2 high chairsbr-wine and cocktail glasses, coffee mugsbr-Keurig & podsbr-12 cup Brewstation coffeemakerbr-blenderbr-crockpotbr-kettlebr and an assortment of small kitchen gadgetsbr(paper towels, dish soap, dishwasher pods, trash bags, coffee, creamer, sugar, teas, honey, olive oil, and seasonings provided)brbrMAIN LEVEL: SUNROOM/DINING ROOM/LIVING ROOM/EXECUTIVE OFFICE & HALF BATHbrbrAdjacent to the kitchen, the bright and cozy sunroom features a new sofa, heated floors, tall windows, and skylights, providing a perfect spot to unwind. Settle in with a good book and listen to the soothing waves of Lake Michigan while enjoying your morning coffee or watching the graceful deer!brbrFreshly furnished living room with fireplace, sofa, swivel chair, and remote-controlled AC. Local guidebooks are in a basket, and playing cards are in the end table drawers. brbrThere is a large family dining table with seating for 8 and additional bar stool seating for 6 around the granite kitchen island. The cocktail cabinet is stocked with assorted glasses, wine/bottle openers, a cocktail shaker, and wine stoppers. brbrRemote workers will appreciate the private office room, equipped with a desk and rolling chair, monitor, printer with ink, copy paper, sofa, built-in bookcases with books for all ages and interests, and a writing desk.brbrTREEHOUSE/DECK/BACKYARD & BEACH FUNbrbrThe expansive three-tiered deck has plenty of seating and play space, a gas grill, and a fire table with propane provided. There is an inground fire pit in the backyard with complimentary firewood (when available- firewood is not guaranteed).brbrTREEHOUSE- Kids and teens will enjoy hanging out in the furnished treehouse with indoor and outdoor lighting, a kid-size futon, and a Papasan chair. Here, they’ll find more board games, coloring books, a PlayStation 3 with several games, and a tote full of artificial flowers for creating an outdoor fantasy garden.. brbrThere is an infant/toddler swing for our youngest guests. The playground at the end of the street by the fire station has basketball goals, soccer nets, swings, and slides.brbrIn the garage, you'll find an assortment of outdoor toys, including 2 adult Trek bikes, 2 children's bikes, a beach wagon, cooler, and sand toys. Beach towels are located in bins in the foyer. brbrWith ample space for family fun and a serene atmosphere, Curtiss Castle beckons you to spread out and relax. Whether you prefer to indulge in activities near the enchanting Lake Michigan or immerse yourself in the world-class golf courses nearby, this retreat will serve as your home away from home.brbrThis home is privately owned and professionally cleaned before each booking. brThe maximum number of guests is 11, including children and infants. No parties, pets, or additional guests are permitted.brbrSecurity Cameras: There are 3 outdoor security cameras (front door, back door main entrance, and treehouse facing fire pit to monitor fires) and one in the garage to allow us to ensure the garage doors are closed and the bikes are put away. There are no cameras inside the house.

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Bath

Sleeps

$223.56

/ Nightly

Private Vacation Home

LUX Uptown Escape - The Trester

Sheboygan, Wisconsin, United States

Welcome to our beautiful 2-bedroom historic home in Uptown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep.brbrStep inside and be greeted by the character and charm of this 1885 historic home. The living area boasts tasteful furnishings, creating a cozy atmosphere for relaxation after a day of exploring. The fully equipped kitchen provides all the essentials for preparing delicious meals, and a dining area is perfect for enjoying them together.brbrThe bedrooms are thoughtfully designed to provide a peaceful night's sleep. Both rooms feature comfortable king beds with quality linens and ample storage space for your belongings. The clean and modern bathroom offers a refreshing shower and essential amenities.brbrBut the true gem of this property lies in the backyard. Step outside and be transported to your private oasis. The beautifully landscaped yard features a grilling area, perfect for cooking up a mouthwatering barbecue. And when night falls, gather around the outdoor movie screen for a memorable movie night under the stars.br

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Bath

Sleeps

$279.02

/ Nightly

Private Vacation Home

2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

Sheboygan, Wisconsin, United States

Modern/updated 2 bedroom 2 bath townhouse on a quite Cul-De-Sac in Sheboygan, WI. Every part of this house has been remodeled with design and detail in mind. AMAZING kitchen upgrades- Quartz countertops, a custom tile backsplash, stainless steel deep sink and beautiful kitchen faucet...this kitchen will not disappoint! The house also features new plank flooring throughout the first floor along with a floor to ceiling natural stone fireplace for those cool/cozy nights. The main floor includes one bath, living room, dining room and kitchen. The kitchen is fully stocked with all your needs and has all new Stainless steel appliances. Both bathrooms have tiled showers, new flooring and countertops. The two bedrooms both have BRAND New queen size Comfy mattresses and both are located on the second floor with another bath. A custom Rustic wood plank feature wall which includes a barn door to the bath is the first thing you see as you walk up the stairs.. The large deck is right off of the Dining room which looks out into the yard which has a large pond and Hot Tub! It's a nice peaceful country setting in the city.brbrThe house is minutes away from Lake Michigan and all that Sheboygan has to offer. The surrounding areas have so many attractions throughout the year, there is always something to do or see.brbrPopular destinations in the area include:brbr*Sheboygan Riverfront restaurants and shops 4 milesbr*American Club in Kohler 6 milesbr*Black Wolf Run Golf Course 6 milesbr*Historic Elkhart lake which includes Road America 20 milesbr*Whistling Straights Golf Course 12 milesbr*Kohler-Andrae State Park 3 milesbrbr

Bed

Bath

Sleeps

$383.06

/ Nightly

Private Vacation Home

Cozy Corner Cottage - Dutch Colonial Step from Beach

Sheboygan, Wisconsin, United States

Welcome to Cozy Corner Cottage — Presented by Great Lakes Getaways! brbrTake advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026.brbrThis charming Dutch Colonial house in Sheboygan’s historic Ellis District is just steps away from Deland Park’s beach, offering an ideal family retreat. Featuring three cozy bedrooms, a fully equipped kitchen, and a comfortable living space with entertainment options, it’s perfect for both relaxation and adventure. Enjoy beach access, explore the historic neighborhood, and make unforgettable memories.brbrDiscover timeless charm and modern comfort in this classic Dutch Colonial home, nestled in Sheboygan’s historic Ellis District. Just a short stroll from beautiful Deland Park and Lake Michigan’s sandy shores, this home is the perfect blend of cozy retreat and convenient location — ideal for families, couples, and small groups looking to unwind and explore.brbrWhat you’ll love:brbr✔ Beach AccessbrEnjoy the beach supplies stored in the front closet, perfect for enhancing your time at nearby Deland Park.br✔ Comfortable Living SpacebrThe living room offers ample seating and a smart TV for entertainment, alongside complimentary high-speed WiFi to stay connected during your stay.br✔ Fully Equipped KitchenbrThe kitchen comes with everything you need, from cookware to spices, making it easy to prepare meals at home.br✔ Cozy BedroomsbrUpstairs, three bedrooms provide a restful space for your group. The master bedroom features a queen-size bed with an ensuite half bathroom, while the second bedroom has a twin-over-full bunk bed perfect for children. The third bedroom, also with a queen-size bed, offers plenty of storage.br✔ Relaxing BathroombrChoose between the walk-in shower or a soothing soak in the bathtub, with fresh towels provided for your convenience.br✔ Historic NeighborhoodbrTake a leisurely stroll through the Ellis District and admire the beauty of the neighborhood’s historic architecture, adding a unique charm to your stay.brbrWhether you’re visiting Sheboygan for a fun family vacation or a peaceful beach getaway, our home in the heart of the Ellis District offers a comfortable, convenient, and memorable retreat. Book your stay today and make lasting memories with your loved ones.brbr :brJohn Michael Kohler Arts Center – 1 mile (4 min)brAbove & Beyond Children’s Museum – 1 mile (4 min)brEllwood H. May Environmental Park (Maywood) – 2 miles (7 min)brbr & :brBlack Pig – 1 mile (4 min)brThe Duke of Devon – 1 mile (4 min)brLino Ristorante Italiano – 1.5 miles (6 min)brbr & :brSheboygan Brat Days – AugustbrHoliday Parade – NovemberbrMaywood Earth Ride – MaybrbrRental Agreement Notice:brGuests are required to review and sign a rental agreement prior to check-in. The agreement includes important house rules and stay policies. Booking this property confirms that you agree to review and complete the rental agreement before your stay. Failure to complete the agreement may result in cancellation of the reservation.

3

Bed

2

Bath

7

Sleeps

$264.88

/ Nightly

Private Vacation Home

At River's Edge - Charming 2BR River Retreat with Garage

Sheboygan, Wisconsin, United States

Welcome to Riverside Drift — Presented by Great Lakes Getaways! brbrEscape to this spacious 2BR, 1.5BA Sheboygan retreat! The king suite features a private balcony and cozy fireplace with serene river views. The second bedroom offers two queen beds, perfect for families or friends. Enjoy an open-concept living space, modern kitchen, in-unit laundry, and plenty of parking with a 2-car garage plus extra space. Minutes from Lake Michigan and downtown!brbrUnwind in comfort at Riverside Drift, a peaceful and spacious 2-bedroom, 1.5-bath retreat overlooking the serene Sheboygan River. Perfect for families, couples, or small groups, this home sleeps up to 6 guests and offers the ideal mix of relaxation, convenience, and unbeatable location on Wisconsin’s Fresh Coast.brWhether you're here for a weekend escape, a family vacation, or an extended stay, Riverside Drift is your perfect home base in Sheboygan.brbrRoom for Everyone — Sleeps 6 ComfortablybrbrThis family-friendly home includes 3 cozy beds and plenty of space to spread out:br- King Suite with a private balcony + fireplace and peaceful river viewsbr- Second Bedroom with Two Queen Beds — perfect for kids, friends, or extra guestsbrbrAmple storage for luggage and clothing during longer staysbrbrA perfect setup for families traveling together or friends enjoying a getaway.brbr- 1.5 Bathrooms + Laundry for Added EasebrEnjoy extra convenience with:brbr- Full bathroom upstairs near both bedroomsbrbr- Half bath on the main level for easy accessbrbr- Upstairs laundry (washer & dryer) — ideal for beach trips and extended staysbrbr- Fully Equipped Kitchen + Open Living SpacebrFeel right at home with everything you need:brbr- Modern, fully stocked kitchen for home-cooked mealsbrbr- Coffee mornings made easybrbr- Cozy living room for relaxing after a day of adventurebrbr- Open-concept layout perfect for quality family timebrbrStress-Free Parking + Attached 2-Car GaragebrNo street parking hassles here!br- Attached 2-car garagebr- Additional parking directly in front of the garagebrbr- Direct walk-in access makes arrival simple in every seasonbrbr- Riverside Views + Cozy Balcony Fireplacebrbr- Step outside to enjoy beautiful Sheboygan River viewsbrbr- Private balcony fireplace for cozy eveningsbrbr- Perfect spot for morning coffee or sunset unwindingbrbr- Peaceful, scenic, and truly relaxing.brbrPrime Location Near Sheboygan’s Best AttractionsbrYou’re just minutes from everything that makes Sheboygan unforgettable:br- Lake Michigan beachesbr- Sheboygan Lighthousebr- Deland Park (pickleball, tennis courts, lakefront trails)br- Sheboygan Riverwalkbr- Downtown dining, shops, and local favoritesbr- Nearby golf courses and outdoor adventuresbrbrSheboygan is known for its lakefront charm, family-friendly atmosphere, and endless vacation opportunities.br- The Perfect Wisconsin Fresh Coast GetawaybrWhether you're visiting for:br- Beach days & sunsetsbr- Pickleball weekendsbr- Festivals & local diningbr- Riverside relaxationbrbr…Riverside Drift has everything you need for a comfortable, memorable stay.brbrBook your stay today and let Great Lakes Getaways host your next Sheboygan adventure at Riverside Drift!brbrRental Agreement Notice:brGuests are required to review and sign a rental agreement prior to check-in. The agreement includes important house rules and stay policies. Booking this property confirms that you agree to review and complete the rental agreement before your stay. Failure to complete the agreement may result in cancellation of the reservation.

Bed

Bath

Sleeps

$737.61

/ Nightly

Private Vacation Home

Beachside, Chefs Kitchen, High-End Everything

Sheboygan, Wisconsin, United States

Welcome to our Delightful Seaside Picnic, hosted by Rose and Fern and Sheboygan Vacation Rentals! brbrThis newly renovated home offers a serene retreat just steps from Sheboygan’s stunning shoreline (and biggest and best beach in the area) where you can enjoy a sunrise stroll along the sandy beach or a refreshing dip in the lake. brbrNestled in the charming Ellis Historic District, our home is also just a short walk from the vibrant riverfront and downtown area, where you can explore a delightful array of local restaurants, cafes, boutique shops, and entertainment. The road end also offers easy access to the lovely Sheboygan North Pier and lake walk.brbrOur spacious home has been thoughtfully designed for comfort and style, featuring a bright, open floor plan and a beautifully appointed kitchen equipped with modern appliances and ample counter space – perfect for cooking up a feast or hosting dinner with family and friends. Throughout the home, you’ll find unique handcrafted furniture (Beds are hand crafted by the owner, a renowned furniture designer and woodworker), ultra high-end MillerKnoll seating in the living room, and artwork created by local artisans, adding a touch of Sheboygan’s artistic spirit to your stay.brbrThe neighborhood is quiet, safe, and brimming with historical charm. You'll love the tree-lined streets and classic architecture, making it an ideal place for leisurely walks. For those who enjoy an active lifestyle, Sheboygan is known for being incredibly walkable and bike-friendly (we provide the bikes), with scenic trails along the lake and river. During the summer months, hop on the local trolley for a nostalgic ride through town, or rent one of the many available scooters to explore at your own pace. Public bus transportation is also conveniently accessible for easy travel around the area.brbrWhether you’re here for a relaxing beach getaway, a culinary adventure, or to immerse yourself in the local culture, Rose & Fern’s Delightful Seaside Picnic offers the perfect home base for your Sheboygan experience. brbrWe look forward to welcoming you!brbrAfter requesting your reservation, you will receive a notification and link to complete our Rental Agreement, confirming the terms and conditions of your stay at Rose & Fern's, as well as the refundable security deposit, which you will be able to execute and set up digitally. brbrPlease note that cancellation fee is 3% to cover the credit card transaction fees.

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Bath

Sleeps

$1285.98

/ Nightly

Private Vacation Home

Walk to Beach & Pier | Fully-Loaded Kitchen

Sheboygan, Wisconsin, United States

✨ Welcome to the Huron House, hosted by Sheboygan Vacation Rentals ✨brbrA beautiful classy remodeled 5-bedroom, 4-bath home just a short walk from Sheboygan’s nicest public beach and the iconic North Pier. Enjoy lake breezes, neighborhood charm, and easy access to dining, shopping, and family fun.brbrbr The HomebrbrBright, open layout with cozy living room + fireplacebrFully equipped kitchenbrLarge dining table for family meals + gamesbrCurated furnishings + thoughtful touches throughoutbrbrbr Office SpacebrDedicated workspace with desk, monitor & printer — ideal for remote workbrbr Bedrooms & Bathroomsbr5 comfortable bedrooms — space for everyonebr4 modern bathrooms — no waitingbrbrbr ‍♂️ Walkable LocationbrbrStroll to:brLake Michigan’s best public beachbrThe North PierbrRestaurants + shopsbrIce cream + coffeebrSeasonal farmers marketbrbrbr Short Drive To:brbr⛳ World-class golf at Kohlerbr Road America auto racingbr ️ Kohler-Andrae State Park + sand dunesbrbrbr What You’ll LovebrbrIdeal for families & groupsbrPeaceful, tree-lined neighborhoodbrStylish + comfortable interiorsbrClose to everything you want to dobrbrWhether your stay is for the beach, the golf course, the race track, or just a quiet getaway — the Huron House is the perfect place to settle in, reconnect, and make memories.br brbrbr✨ We look forward to hosting you!brbr- After booking your reservation, you will receive a notification and link to complete our Rental Agreement, confirming the terms and conditions of your stay at The Huron House, as well as a refundable security deposit, which you will be able to execute and set up digitally.brbr- Pet Fees: $55/dog per night. Please notify us at booking if you plan to bring a dog. $500/night fine for each animal present if not notified.

5

Bed

4

Bath

11

Sleeps

$1879.23

/ Nightly

Private Vacation Home

Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery!

Sheboygan, Wisconsin, United States

Located on a dead-end street, this 4 bedroom home is less than 15 minutes away from Whistling Straits and many other golf courses and walking distance to Blind Horse Winery. Located just north of Kohler, the Kohler Water Spa and Shops at Woodlake are just 2 miles down the road. brbrThe private backyard is fully fenced in with a deck-great for cooking out. Gas grill and gas bonfire pit included. The perfect setup after a long day at the course. brbrThis home offers a master with an attached full bath and an additional half bath on the main level. There are three bedrooms upstairs along with another full bath. ! Note: the bedroom pictured with a crib will be outfitted with a full size bed. brbrThe three-car garage will fit one vehicle. The remaining space is used for a gym. Feel free to get a workout in while you are here. Don't worry, the driveway offers plenty of additional parking.

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Bath

Sleeps

$225.81

/ Nightly

Private Vacation Home

Good Vibes on the Third Coast-Pet Friendly! Cozy and Close by!

Sheboygan, Wisconsin, United States

Peaceful bohemian retreat filled with warmth and a lively vibe! Perfect for couples, remote workers, girls weekends, golf outings and families! brThe house is spacious with 4 bedrooms (3 Queen beds, 1 Full, 1 Bath) with a well stocked kitchen, inviting dining area, cozy living space, comfy beds, a front porch and a fenced in backyard! Enjoy a cup of coffee, listen to a record or relax on the hammock. We supply a French press coffee maker as well as a 6 cup coffee maker. Lots of coffee for all your mornings and a grinder to keep it fresh.brIf you have a hunger spot we also have snacks and microwave popcorn for our guests to enjoy!brCome and hang out outside!!! brWe have a lovely fenced in backyard, grill for outdoor cooking, a fire pit (we don’t supply wood but you are welcome to get some just down the street at Trillings the local hardware store) and a corn hole game to enjoy! We have a picnic area and gazebo as well for guests enjoyment. brbrWe also provide 4 beach chairs, beach towels an inflatable paddle board ( and life jackets) to use. If you would like to to bike around let us know!! We provide 2 beach cruisers and a kids trailer!brbrOur neighborhood is a safe and family friendly . It has has lots of architectural charm from Dutch and German settlers. It is very walkable with multiple parks nearby and close to downtown. The house is a 3 minute drive or short bike ride to the Sheboygan's beautiful lakefront. Take a dip in Lake Michigan, watch the local surfers catch some waves or enjoy the ever changing sunset! brWhatever brings you here, we look forward to your visit. Come and enjoy everything Sheboygan has to offer!brbrbrFeel the vibes of the Third Coast and cherish the days!!brbrThings that we ask when booking, Guidelines for the house:brbr*Please respect of our home!br*No smoking, parties or candles. *No additional guests unless communicated with us. No weapons allowed on property. No drugs allowed on property. No smoking or tobacco of any kind. (If there is any evidence we will charge a $375 fee)brbr*Please take off shoes when entering our home. (No shoes inside) We recently refinished our floors ourselves so it has been quite the labor of love.brbr*Up to 2 well behaved dogs are allowed. $150 pet fee. Please bring a crate for them when you have to head out)br brbr*Please be respectful of our neighbors, we are in a family friendly neighborhood.brbr*Quiet hours from 9pm-8am.brbr*Also Failure to follow check out instructions and VRBO standard of “Leaving the listing in the condition it was received” will result in an additional $110 /hour cleaning fee. If a pet or person damages any part of the property a $375 fee will be charged.

4

Bed

1

Bath

6

Sleeps

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