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, 311 reviews

The A-frame cabin is framed by lush greenery and colorful landscaping. A welcoming pathway leads to the entrance, featuring a spacious deck. The cabin's dark exterior contrasts with the surrounding trees, creating a serene and private atmosphere.

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.

4.98 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, 106 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.

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, 144 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.

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.

4.98 out of 5 average rating, 182 reviews

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, 194 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.

4.92 out of 5 average rating, 157 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.

Apartment in Manitowoc

Lakeshore Bungalow Boutique

Newly remodeled upstairs 2 bedroom, very spacious apartment. Shaby sheek style downtown very cute home away from home. Just minutes from beautiful biking and walking trails and beaches along the beautiful shores of Lake Michigan. Walking distance to restaurants, pubs, wine bar, museums, beaches, shopping, grocery store, bakerie, zoo, car ferry, gym's, coffee shops, library. Beautiful lake Michigan Marina and Light House, Manitowoc is a very cute and quaint small town.

4.97 out of 5 average rating, 233 reviews

A rustic living area is highlighted by exposed log walls and hardwood floors. A stone fireplace is centered against one wall, while a comfortable plaid sofa faces a wooden coffee table. A dining table is set for meals, featuring simple floral decor.

Farm stay in West Bend

Family friendly farmstay just outside Milwaukee

The Inn at Paradise Farm is an original 1847 log homestead in rural Wisconsin just a short drive from Milwaukee and close to many attractions, especially for nature lovers. Our very spacious private 4-room suite with private entrance is comfortable for couples, families, or business travelers who long to unwind in a pastoral setting. Visit with, and even help care for, our friendly animals! We are licensed and inspected. Paradise Farm welcomes all.

4.99 out of 5 average rating, 303 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.

A green chair is positioned next to a circular mosaic table, offering a spot to relax. In the background, a wooden railing encloses a patio area with additional seating visible. Lush greenery from surrounding trees adds a natural touch to the inviting outdoor space.

4.91 out of 5 average rating, 150 reviews

Spacious Home Near Lake MI w/ Fire Pit

Welcome to the Relax ‘n Retreat! Retreat: noun - a quiet or secluded place in which one can rest and relax Unwind at our 3 bedroom home 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. Send me a message to find out about our other available listings.

Popular amenities for Plymouth outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.9 out of 5 average rating, 157 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

The living room features a light, airy space with a large window offering a view of Lake Michigan. A cozy white sofa is complemented by a striped chair, and a wooden coffee table holds decorative items. Soft lighting illuminates the room, enhancing its inviting atmosphere.

4.96 out of 5 average rating, 125 reviews

Bright and Beautiful Lake Escape

4.94 out of 5 average rating, 54 reviews

A cozy sitting area is highlighted by a gentle glow from a nearby lamp, featuring a soft gray couch and a matching rocking chair. A round mirror reflects the light and a small table holds a book and decorative items, while the kitchen is visible in the background.

Home in Manitowoc

Upper Lake Boulevard Retreat

4.94 out of 5 average rating, 17 reviews

Home in North Point

Beach Break - Historic Home Meets Modern Comfort

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

A tranquil view of Lake Michigan at sunset, where calm waters reflect soft hues of orange and pink. The sky showcases wispy clouds, and a distant bird is seen soaring above the serene landscape, creating a peaceful setting.

4.94 out of 5 average rating, 209 reviews

Beachfront getaway in Sheboygan

4.9 out of 5 average rating, 145 reviews

Home in Two Rivers

The Smiling Bear Cabin | 45m to Lambeau! Lakeviews

4.95 out of 5 average rating, 201 reviews

An A-frame structure is set against a colorful sunset, featuring a welcoming entryway and large windows. A hot tub is positioned on a deck next to the home. Two adirondack chairs are placed on the lawn near a smokeless fire pit on a tree stump.

Home in Hilbert

State Park Getaway with Hot Tub & Arcade

Apartment rentals with outdoor seating

Apartment in Port Washington

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

Apartment in Port Washington

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*

A modern kitchen features gray cabinetry and a spacious island with seating for two. Stainless steel appliances, including a microwave and stove, are visible. Natural light filters through a nearby window, and a floral centerpiece adds a touch of color to the countertop.

4.96 out of 5 average rating, 27 reviews

Terrace View a Charming 1 Bedroom Apt

Apartment in Ellis Historic

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.

4.98 out of 5 average rating, 211 reviews

Modern Upstairs Apt - Steps from Lake Michigan

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.

4.93 out of 5 average rating, 42 reviews

Parkside Studio Apartment

Apartment in Campbellsport

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.

4.97 out of 5 average rating, 104 reviews

GGG Spacious Log Cabin apartment on the IAT

Apartment in Port Washington

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.

4.98 out of 5 average rating, 201 reviews

Inn on Billy Goat Hill

5 out of 5 average rating, 28 reviews

Clean, Comfy Stay Near Parks, Downtown & Lake!

Condo 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.

Condo 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, 49 reviews

A Glorious Getaway Sheboygan - LUX Lake Condo

An open-concept living area features a cozy gray sofa and a round dining table with light-colored chairs. A modern electric fireplace is positioned beneath a large wall-mounted TV. Natural light floods in through expansive sliding glass doors, leading to a furnished balcony.

4.86 out of 5 average rating, 22 reviews

Modern South Pier Condo on Sheboygan River!

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, 115 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.

Condo in Manitowoc

Cream City Flat - Boutique Condo