Pet-friendly holiday rentals in Sheboygan

The kitchen features a spacious granite countertop and a black sink, highlighted by wooden cabinetry. A large window allows natural light to fill the room, showcasing scenic outdoor views. Colorful yellow chairs and a small table create a cozy seating area nearby.

4.97 out of 5 average rating, 136 reviews

Lakefront Charmer, cheerful decor gorgeous garden

This 2600 sqft lakefront home is a spacious retreat year round, friendly to kids and dogs. It is perched upon a bluff overlooking Lake Michigan with a gorgeous sunrise view. In winter, enjoy passing cargo ships and eagles along with ice formations. Inside, dine with seating and service for 12 after cooking in the spacious kitchen with wood fireplace. Kitchen, living room, dining room and 2 bedrooms have full lake view. 2 large screen tvs. Spa quality bath with whirlpool. Gas fireplace too!

4.92 out of 5 average rating, 264 reviews

A rustic modern home is showcased, featuring a spacious wraparound deck surrounded by lush greenery. An inviting hot tub glistens in the sun, and an arcade room with various games is displayed, offering entertainment options for guests.

Home in Elkhart Lake

The LODGE in Elkhart Lake. —-Hot Tub & Arcade—-

Rustic modern home w/ hot tub, arcade & fireplace right on the edge of Elkhart Lake. Road America, great golf, The Ice Age Trail, & the Kettle Moraine are all at your doorstep. This cozy home is 4 blocks from the downtown of Elkhart lake. Yet it still has an acre to explore & enjoy nature. Only 4 miles from Road America. 2 bedroom w/ 2 extra sofa sleepers & 2 baths. Perfect for racers or romantic getaways. The arcade/Pinball room has over 10 games. Perfect base camp. We got your bases covered

A cozy living area is filled with neutral-toned furniture, including a large sofa, accent chairs, and a circular coffee table. Natural light filters in through large windows, highlighting the wooden floors and a decorative area rug beneath. Soft green accents are present in the lamps and curtains.

4.98 out of 5 average rating, 123 reviews

House Near the Lake

Get out and enjoy nature, then return to a quiet mix of modern and retro in this family home only a block away from Lake Michigan. There are three parks and two beaches within a mile, as well as Terry Andrae State Park about 10 minutes away. If the outdoors aren't your thing, downtown Sheboygan hosts the Kohler Art Center, The Weil Center, Blue Harbor, and the Children's Museum, with Road America only 30 minutes away. Located between Milwaukee and Green Bay, this home has all the conveniences.

4.9 out of 5 average rating, 111 reviews

A cozy living room is featured, with a dark sofa, light-colored chairs, and a round pouf. A woven pendant light hangs above, illuminating textured wall art. Natural light filters through multiple windows, highlighting a striped area rug laid on the wooden floor.

Flat in Sheboygan

The Beach | Sheboygan 2Br/1 Ba

Welcome to the Beach, a lakeside retreat in the heart of Sheboygan. Located just 3 blocks from Lake Michigan and a stones throw to down town Sheboygan, The Beach is the perfect place to center your visit to Eastern Wisconsin. The Beach is the main floor unit of a duplex featuring 2 bedrooms, 1 bathroom, a well stocked kitchen, a cozy living room, fast wifi and convenient amenities. We have an easy check out with no to-do lists. Just pack and go! *New cleaning staff hired January 2023!*

A wooden shelf is mounted on a gray wall, displaying a collection of colorful ceramic mugs hanging from hooks. Above the mugs, a white container holds green plants, while a coffee bag is placed alongside framed artwork.

4.93 out of 5 average rating, 267 reviews

Dog Friendly Blue Door Cottage / Fully Fenced Yard

Nobody should have to leave their fur baby behind while on vacation. This is exactly why we created this comfortable home with your family & puppy in mind. You'll be at ease knowing that your pooch will be having just as much fun as you are. Modern hints are complemented by the cozy, welcoming decor found throughout. The coffee bar is a fav for any morning person, and the "take-a-wine leave-a-wine" wine bar offers evening excitement! The huge yard features a fire pit, gas grill, & cornhole.

The kitchen area offers light wood cabinetry and a breakfast bar, with a dining table that seats four. Large sliding glass doors provide views of the lake, while ample counter space accompanies a full-size refrigerator and modern appliances.

4.86 out of 5 average rating, 218 reviews

Dog Friendly Cozy Cottage Rental on Lake Michigan!

Kohler Design Center Rentals, Kohler Andrae State Park Rentals, Whistling Straits Rentals, Blue Harbor Rentals, Road America Rentals, Kohler Art Center Rentals, Black Wolf Run Rentals, Lake Michigan Fishing Charters Rentals, Green Bay Packer Rentals, Door County Rentals, Honeymoon Rentals, Women's Weekend Rentals, Lake Michigan Sunrise Rentals, Dog Friendly Rentals, Winter Rentals. Dog Friendly Rentals, Sheboygan, Wisconsin Rentals, Saugatuck, Michigan Rentals, New Buffalo, Michigan Rentals

4.95 out of 5 average rating, 154 reviews

A modern single-story home features a light gray exterior with a striking yellow front door. Large windows provide abundant natural light, while a well-maintained lawn is complemented by colorful flower beds. Skylights on the roof enhance the home's contemporary design.

Home in Cleveland

Modern Home Just 40 Minutes from GB NFL Draft

My home is just minutes from Whistling Straits Golf, Road America, Lake Michigan, Parks, Hiking, Biking, Snowshoeing, and Cross Country Skiing. You’ll love my place as it's newly remodeled, modern & cozy. The kitchen and living areas have high ceilings, sky lights & new furniture. The large outdoor living area is perfect for social time. My favorite is the heated bathroom floors. My place is perfect for golfers, wedding groups, couples, business travelers, and families (with kids & dogs).

4.96 out of 5 average rating, 170 reviews

An aerial view of a spacious home is surrounded by mature trees, showcasing a private sandy beach alongside Lake Michigan. The property features a pathway leading to the house, emphasizing its secluded setting amid natural greenery.

Home in Oostburg

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

4.98 out of 5 average rating, 183 reviews

A well-lit living area features a neutral-colored sofa adorned with a soft throw. A glass coffee table sits on a patterned rug, complemented by a wicker basket. Natural light filters through the window, illuminating the space and the nearby armchair.

Flat in Sheboygan

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

A welcoming living area is highlighted by a warm orange couch with blue accent pillows. A modern lamp with a red base stands beside it on a side table. A framed painting adds character, while a plant is visible through a doorway leading to another room.

4.95 out of 5 average rating, 132 reviews

King Bed Near Lake w/ Fire Pit & Pack N Play

Welcome to the Getaway! Getaway: noun - an act or instance of getting away; a place suitable for a vacation You will unwind in this peaceful 3 bedroom lower unit near Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening around the fire pit, or if you don’t feel like staying in, head out to discover some of Sheboygan’s many hidden gems. If this unit is booked for your dates, send me a message to ask about our other available listings.

Flat in Downtown Sheboygan

A compact kitchen area showcases modern cabinetry and essential appliances, including a refrigerator and a stove. A small counter with two stools provides a space for dining or working, accented by natural light filtering through a window. Decorative elements enhance the inviting atmosphere.

4.84 out of 5 average rating, 245 reviews

Sheboygan Surf House - Jetties

Located just 24 steps above Wisconsin's first Surf Shop, EOS Surf. Our Urban living oasis is a fully equipped studio apartment conveniently located in the heart of downtown, just steps from bars and restaurants and only blocks to Lake Michigan South Pier and Blue Harbor. Whether you are here for adventure sports like Surfing on the Great Lake, Kite boarding, charter fishing, a Wedding or leisure time SSH is perfect for you. Support Dog friendly

Superhost

A view of the serene shoreline along Lake Michigan is presented, framed by lush greenery. A blue railing leads down toward the beach, where sand and water are visible, inviting outdoor activities. The sky is overcast, creating a calm atmosphere.

Guest house in North Point

4.82 out of 5 average rating, 501 reviews

Carriage House Sheboygan, Lake Mich beach access!

The Carriage House is the perfect getaway. Located in a beautiful historic neighborhood with Lake Michigan public beach access across the street, 100 yards away. Ideal for a family of four or an individual in town for business. Amenities have been thoughtfully placed to create the most comfortable and convenient stay for guests. We pride ourselves on ensuring you enjoy your stay with us and guarantee you'll love the neighborhood!

Popular amenities for Sheboygan pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

The main living area features a mix of seating options, including a modular sectional sofa and lounge chairs. A decorative area rug sits under a circular coffee table, while large windows offer views of the surrounding greenery. A fireplace enhances the inviting ambiance.

5 out of 5 average rating, 32 reviews

Norwind Ranch - Peaceful Retreat Near Road America

5 out of 5 average rating, 20 reviews

A charming white house is seen nestled among lush green trees and colorful foliage. A well-manicured lawn leads up to the front porch, which features a dark roof and an inviting entryway. A white picket fence outlines the property, enhancing its quaint appeal.

Home in Plymouth

Riverside House

5 out of 5 average rating, 22 reviews

Home in Oostburg

Winter's a good time to stay in&cuddle at Surfdaze

A well-lit game room features an air hockey table with blue LED lighting, a green pool table, and a bar area with seating for four. A washer and dryer unit is positioned against the wall, while a television is mounted for entertainment.

4.95 out of 5 average rating, 20 reviews

Relax & Play- Walking distance to food & drinks

A dedicated golf space features a high-definition simulator and a vibrant artificial turf area. Nearby, a foosball table and a bar-height table with stools are visible, while a golf bag rests on the floor. Natural light enters through a nearby window.

5 out of 5 average rating, 19 reviews

The Links! - Luxury Golf Retreat

4.99 out of 5 average rating, 86 reviews

A spacious living area is highlighted by large windows allowing natural light to fill the room. Comfortable seating includes a sectional sofa and two armchairs, arranged around a stylish fireplace with intricate tile work. Light-colored curtains complement the modern decor.

Home in North Point

The Suncatcher -Steps from Lake - Fenced Yard

The dining area features a wooden table set with dark bowls and glassware, illuminated by a soft, modern light fixture. Natural light filters in through two large windows, casting a warm glow on the space. A decorative runner is placed center on the table.

5 out of 5 average rating, 26 reviews

Stylish brick cottage - family & pet friendly

4.99 out of 5 average rating, 81 reviews

A spacious living area is centered around a circular glass table with a potted plant. Comfortable gray sofas frame the space, accompanied by two blue chairs. A stone fireplace adds warmth, and large windows allow natural light to fill the room, displaying views of the outdoors.

Home in Cleveland

Wake on the Lake - Minutes to Whistling Straights

Pet-friendly home rentals with a pool

A spacious room features a king-size bed with a textured blanket. Modern appliances, including a refrigerator, are visible. A television is mounted above a decorative fireplace, and a small desk with a chair is positioned nearby. Natural light is welcomed through a door leading to the outside.

Hotel room in Elkhart Lake

Sleeps 8! 2 Full Bath with Kitchenette!

A spacious room features two large beds adorned with patterned bedding. Natural light filters through sliding glass doors leading to a balcony. A ceiling fan enhances airflow, while a large mirror and dresser provide functional space. A blue area rug adds a cozy touch to the hardwood floor.

Hotel room in Elkhart Lake

4.33 out of 5 average rating, 6 reviews

Stay in the heart of Elkhart Lake at Victorian Inn Resort

5 out of 5 average rating, 11 reviews

A living room featuring large windows that provide views of the surrounding landscape. A patterned armchair invites relaxation alongside a small side table. A white fireplace serves as a focal point, with a stylish arrangement of decorative items above it. A soft area rug covers the hardwood floor.

Flat in Elkhart Lake

Resort Condo on Elkhart Lake

Hotel room in Elkhart Lake

A well-lit room features two spacious beds dressed in crisp white linens. A flat-screen television is mounted on the wall, while a dresser provides storage. A small desk is set against one wall, accompanied by a decorative indoor plant in a pot.

5 out of 5 average rating, 9 reviews

Resort Life 2 Queen Suite

Private, pet-friendly home rentals

A contemporary living area features a brown leather couch paired with green and gray cushions. A circular mirror is set above a wooden coffee table adorned with a small potted plant. The space includes hanging greenery and a soft area rug, enhancing a calm ambiance.

4.94 out of 5 average rating, 54 reviews

Sleeps 7{SPACIOUS}Pets Welcome!

5 out of 5 average rating, 48 reviews

A spacious living area is observed, featuring a comfortable gray sofa and a coffee table resting on a light rug. Bright windows allow natural light to illuminate the room. A television is positioned on a media console, along with a small dining table and chair set against the wall.

Guest suite in Plymouth

Downtown Plymouth, WI Second Floor 2 Bed Apartment

5 out of 5 average rating, 22 reviews

An aerial view showcases the cabin nestled among lush greenery, adjacent to a serene lake. A well-maintained path leads from the home to the water's edge, framed by trees reflecting vibrant autumn colors. The peaceful landscape invites relaxation and exploration.

Cabin in Cascade

Lakeside Cabin Retreat Magical Holiday Hideaway!

5 out of 5 average rating, 20 reviews

A welcoming entrance features a spacious porch with a red accent wall and decorative flower boxes. Steps lead up to the front door, flanked by a laid concrete pathway and well-maintained grassy areas, providing access to the farmhouse.

Home in Malone

Blue Sky Country Living

4.85 out of 5 average rating, 47 reviews

A welcoming living area features large windows overlooking the lake, allowing natural light to fill the space. A brick fireplace is highlighted against a wall adorned with décor. Comfortable seating is arranged around a decorative table, creating an inviting atmosphere.

Home in Plymouth

Lake Front Cottage With Dock. Walk to Road America

Campervan/Motorhome in Glenbeulah

An inviting outdoor setup features a modern camper surrounded by soft glowing string lights. A cozy seating area is arranged beside a fire pit, with two comfortable chairs and a small table. A grill sits nearby, adding to the campsite ambiance under a sunset sky.

4.88 out of 5 average rating, 40 reviews

Secluded Country Farm Getaway

4.76 out of 5 average rating, 25 reviews

The interior living area features exposed wooden beams and large windows that allow natural light to illuminate the space. Comfortable seating arrangements include sofas and armchairs beside a wood-burning stove. A dining area with a large table is visible in the background, enhancing the open atmosphere.

Cabin in Campbellsport

Peaceful Lakeview Cabin Stay On Private Pennisula