Holiday rentals with outdoor seating in Plymouth

4.97 out of 5 average rating, 186 reviews

The kitchen features dark cabinetry with artistic landscape designs and a large white countertop island. Stainless steel appliances include a stove and dishwasher, while a coffee maker is positioned on the counter. Natural light enters through a nearby doorway, illuminating the warm wood tones of the floor.

Home in Plymouth

The 2400 sq ft Plymouth Paddock near Road America!

This charming two story, 2400 square ft colonial house is the perfect respite for families looking to connect, or race fans looking for a home during race weekend. Only 4 miles from Road America the location is close to all of Sheboygan County's finest attractions. Located two blocks from downtown on a quiet street, its up to you how you want to spend your evening. You could walk downtown for a bite, have a campfire, make a meal, or just spend time together. Welcome to your home away from home!

4.99 out of 5 average rating, 310 reviews

Cabin in Elkhart Lake

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

4.92 out of 5 average rating, 262 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

4.98 out of 5 average rating, 139 reviews

The two-story home features a beige exterior with multiple windows, surrounded by a grassy yard. Two chairs are positioned in front on a small patio area. Large trees provide shade, while a view of the countryside and other structures is visible in the background.

Home in Glenbeulah

Stay at Sunrise LLC, Like being at Grandma's

Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural area, recreation trail head is 3 miles east of us as is the Wade House, 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. We do not have WIFI Phone reception for Internet is good. No Cable or Satellite TV, Over 32 antenna channels. Smoking is allowed outside of the home. No pets allowed.

A bright living area showcases a spacious dining table with place settings, and a cozy red armchair positioned nearby. Large sliding doors reveal an inviting patio space, while a television stands against the wall opposite, enhancing the relaxing atmosphere.

4.97 out of 5 average rating, 105 reviews

Relaxing Sheboygan/Kohler Getaway

Newly remodeled townhouse with all the comforts to make you feel at home in quiet neighborhood, boasting a spacious backyard w/patio, fire pit & free parking. Amenities include well-equipped kitchen, 2 BR & 2 BA, washer/dryer, wi-fi, & smart TV. Conveniently located within minutes to Village of Kohler, Downtown Sheboygan & Lakefront, Black Wolf Run, Whistling Straits (14 min), Road America (18 min), Kohler-Andrae State Park (16 min), grocery stores, restaurants, shopping & local entertainment.

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, 122 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.

Earthen home in Elkhart Lake

A spacious bathroom features wooden walls and ceilings, complemented by large windows providing expansive views of the surrounding landscape. Two circular sinks sit atop a rustic wooden vanity, while a freestanding tub is positioned near the window, enhancing the serene atmosphere. Decorative elements include a chandelier and potted plants.

4.97 out of 5 average rating, 111 reviews

Camp Skywood - Elkhart Lake - Road America

Nestled just minutes from Downtown Elkhart Lake, this custom-built cordwood home offers a secluded sanctuary experience. Perched atop a hill, the unique 16-sided house provides breathtaking views of the state forest and surrounding farmland. Despite its remote feel, you’re only a 5-minute drive from the charming Elkhart Lake business district. Day hikes on the ice age trail are just steps away from the property. Escape to tranquility while staying conveniently close to local attractions.

A cozy backyard oasis is illuminated in evening light, featuring comfortable seating around a fire pit. An outdoor movie screen projects a vibrant image onto the adjacent wall, surrounded by lush landscaping and wooden fencing that enhances privacy.

4.95 out of 5 average rating, 141 reviews

LUX Downtown Escape | Outdoor Movie Screen

Welcome to our beautiful 2-bedroom historic home in Downtown 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. The home is also just a few blocks from Lake Michigan's beautiful beaches.

4.98 out of 5 average rating, 182 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.

5 out of 5 average rating, 191 reviews

Cabin in Cascade

hot tub and sauna on 5 private acres

Looking for a cozy winter retreat? Experience the Bird House, a tranquil Scandinavian-inspired private woodland paradise. Melt away stress in the hot tub and infrared sauna as you take in peaceful views of the meadow. Explore snowshoe and cross-country ski trails nearby in the scenic Kettle Moraine. Stream your favorite movie on the projector near the fireplace or unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee.

4.96 out of 5 average rating, 157 reviews

Home in Plymouth

Oak Haven | Theater • Game Room • Sauna • Firepit

Welcome to Oak Haven, a private 4,300 sq ft retreat surrounded by oak trees and peaceful Wisconsin beauty. 🌿 • 12-seat movie theater with plush recliners & surround sound 🎬 • Game room with pool, ping pong, shuffleboard & poker 🎱 • Infrared sauna + two outdoor fire spots for perfect nights 🔥 • Gourmet kitchen & dining for twelve 🍽️ • Minutes to Kohler golf, Kettle Moraine & Road America 🏎️ ✨ Oak Haven—where relaxation, laughter, and connection come naturally.

4.99 out of 5 average rating, 299 reviews

A relaxing living area features a stone fireplace as its focal point. Comfortable seating options, including a leather chair and a spacious sofa, are arranged around a rustic coffee table. Large windows allow natural light to fill the space, with glimpses of the surrounding scenery.

Cottage in Fond du Lac

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

Popular amenities for outdoor seating rentals in Plymouth

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

Superhost

Home in Oshkosh

4.85 out of 5 average rating, 269 reviews

Cozy Retreat • Fireplace Loft •Walk to Park & Lake

4.9 out of 5 average rating, 156 reviews

A single-story ranch home is depicted, showcasing a well-manicured lawn with green grass and various shrubs. The exterior features a blend of siding and brick, with large windows providing ample natural light. A two-car garage is present on one side of the home.

Home in Manitowoc

Neighborhood home in Manitowoc

4.76 out of 5 average rating, 325 reviews

A charming lakeside home is framed by natural greenery and sits beside the water's edge. A patio area features a fire pit, while a small dock extends into the lake. Trees provide privacy, and the house includes large windows that offer scenic views.

Home in Fond du Lac

Little Lake House

The exterior of a charming house is depicted, showcasing a welcoming front porch with steps leading up. The porch features a small seating area and decorative plants, while lush green grass frames the path, adding to the inviting ambiance.

4.97 out of 5 average rating, 210 reviews

Logan's Guest Nest

Home in Downtown Sheboygan

A living area features plush green chairs arranged around a low table, creating an inviting space for conversation. Natural light streams through nearby windows, illuminating the original woodwork and hardwood floors. A decorative fireplace adds to the room's character.

4.99 out of 5 average rating, 151 reviews

2 Min Walk to Food, 15 to Pier! 4 Bedrooms 2K/2Q

4.78 out of 5 average rating, 144 reviews

A modern, single-story house with grey siding and a spacious two-car garage is shown. A gravel driveway leads to the entrance, framed by green grass and a well-maintained landscape. A small porch is visible on the left side of the home.

Home in Oshkosh

Quiet Country Home close to Lake Winnebago

4.95 out of 5 average rating, 300 reviews

A spacious living room features a stone fireplace and large windows allowing natural light. Comfortable seating arrangements include plush chairs and a patterned area rug, creating a cozy atmosphere. Wood accents and soft colors enhance the open feel of the space.

Home in Two Rivers

Beach Haven, on Lake Michigan.

4.9 out of 5 average rating, 144 reviews

Home in Two Rivers

The Smiling Bear Cabin | 45m to Lambeau! Lakeviews

Apartment rentals with outdoor seating

A spacious dining area features a large wooden table surrounded by eight wooden chairs. A decorative chandelier hangs overhead, while a vibrant painting and ornate mirror enhance the ambiance. A decorative area rug covers the floor, and a vintage radiator is visible in the background.

4.96 out of 5 average rating, 330 reviews

Grace Adventure House, walk to Port, Shops, Beach

A welcome booklet and guest book are displayed on a wooden table. The booklet features a clean design with the text 'Silvers Four Six Six Welcome' printed on the cover. The guest book is smaller and includes a similar design theme, both inviting guests to share their experiences.

4.98 out of 5 average rating, 122 reviews

Silvers Four-Six-Six *A home away from home*

4.92 out of 5 average rating, 156 reviews

The exterior of a two-story home is shown, featuring a gray facade with black shutters. A set of stairs leads to a front porch decorated with potted plants. Colorful flags add a welcoming touch, while a driveway and well-maintained landscaping are positioned in front.

Flat in Manitowoc

Lakeshore Bungalow Boutique

4.98 out of 5 average rating, 208 reviews

A well-lit bedroom features a spacious bed with a dark headboard and light bedding. Two bedside lamps illuminate the room, complemented by natural light from the two windows. A wall-mounted television adds functionality, while a piece of art decorates one wall, enhancing the inviting ambiance.

Flat in Ellis Historic

Modern Upstairs Apt - Steps from Lake Michigan

4.92 out of 5 average rating, 39 reviews

An open living space features a round dining table with four chairs, complemented by a cozy seating area with a sofa adorned in warm tones. Natural light filters through large windows, while string lights add a gentle illumination to the ceiling.

Flat in Sheboygan

Parkside Studio Apartment

4.97 out of 5 average rating, 104 reviews

A dining area is showcased, featuring a wooden table set with two plates. A vase with flowers sits at the center. Large windows frame the view of verdant trees, allowing natural light to fill the space.

Flat in Campbellsport

GGG Spacious Log Cabin apartment on the IAT

The exterior of a two-story home is shown, featuring a beige facade with white trim. A red door adds a pop of color, and flower boxes are mounted under the front windows. In the background, a clock tower is visible, indicating proximity to local attractions.

4.97 out of 5 average rating, 199 reviews

Inn on Billy Goat Hill

The kitchen features a granite countertop with a stainless steel sink, complemented by white cabinetry and a decorative rug. Shelves display colorful dishware, and a doorway leads to the adjoining living spaces.

4.91 out of 5 average rating, 158 reviews

Lighthouse View -a real gem on Sweet Cake Hill

Apartment rentals with outdoor seating

The exterior of a charming building is presented, featuring a distinctive red roof and white siding. A reserved parking space is visible in the foreground, along with colorful flowerbeds that add a vibrant touch. The entrance is framed by a spacious porch, leading to the main entrance.

Apartment in Campbellsport

5 out of 5 average rating, 4 reviews

2BR Condo on a resort on the lake w/beach access

The exterior of a charming two-story building is shown, featuring white siding and red roofs. Stone pillars flank the entrance, and a spacious porch is visible on the lower level. Well-manicured grass and landscaped areas surround the structure.

4.98 out of 5 average rating, 48 reviews

A Glorious Getaway Sheboygan - LUX Lake Condo

A spacious living area is highlighted by large glass sliding doors that offer views of a green landscape. A comfortable sectional sofa is adorned with colorful cushions, complemented by a round coffee table on a patterned rug. A vibrant piece of wall art adds a touch of charm.

4.94 out of 5 average rating, 36 reviews

Heavenly Condo in the Malibu of the Midwest

A serene view from the second-story balcony overlooks the sandy beach and expansive lake. Soft waves lap at the shore under a cloudy sky, with a faint rainbow visible in the distance, creating a tranquil atmosphere for relaxation.

4.95 out of 5 average rating, 65 reviews

Beach condo for 12: 4 bdrms, 2+ baths, treadmill

A bridge is seen raised, allowing a sailboat to pass through the waterway. Clear blue skies provide a backdrop to the scene, while trees with autumn foliage line the riverbank. The calm water reflects the colors of the surroundings.

4.95 out of 5 average rating, 114 reviews

Janelle's Dockside Condo

5 out of 5 average rating, 44 reviews

The main living and dining area features original cream city brick walls. A large dining table is accompanied by black chairs, while a comfortable seating arrangement includes a dark sofa and a light-colored armchair. Natural light fills the space through multiple windows.

Apartment in Manitowoc

Cream City Flat - Boutique Condo

Apartment in Elkhart Lake

A charming Victorian home showcases a light yellow exterior with white trim. The front porch features a welcoming entrance, while bright red Adirondack chairs are arranged on the grassy lawn. A deck is visible on the upper level, surrounded by trees and greenery.

5 out of 5 average rating, 19 reviews

Adorable modern cottage-upper unit