Vacation rentals in Plymouth

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Top-rated vacation rentals in Plymouth

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Guest favorite

Home in Howards Grove

4.95 out of 5 average rating, 151 reviews

Spacious lower level priv entrance no cleaning fee

Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee. Unit NOT set up for babies or toddlers.

Dec 17 – 24

€ 109 per night

Guest favorite

Cottage in Oostburg

4.97 out of 5 average rating, 231 reviews

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Jan 17 – 24

€ 142 per night

Guest favorite

Cabin in Elkhart Lake

4.99 out of 5 average rating, 191 reviews

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.

Aug 29 – Sep 5

€ 274 per night

Guest favorite

Home in Plymouth

4.97 out of 5 average rating, 103 reviews

OakHaven - Insane Game Room, Theater, Large Groups

The search is over, you have found the PERFECT retreat at Oaks Haven! Experience the tranquility of nature surrounded by oak trees and birds. The luxury of a custom-built home (4,300 sq ft) thoughtfully designed for large groups to spread out or gather close. Or connect with friends over the expansive list of amenities including a 12-seat movie theater! The moment you pull in, you will become instant hero for planning the ultimate retreat. At Oaks Haven, we truly have thought of everything!

Dec 9 – 16

€ 718 per night

Guest favorite

Home in Sheboygan

4.96 out of 5 average rating, 153 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.

Mar 8 – 15

€ 157 per night

Guest favorite

Cottage in Fond du Lac

4.97 out of 5 average rating, 234 reviews

Cozy Guest House with Lake views.

Our remodeled two bedroom Guest House is adjacent to our Cottage and offers beautiful lake views. Access to Lake Winnebago available at near by boat launches. 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 bed and 2 twin beds, 1 full bathroom, and a fully stocked newly remodeled kitchen. Perfect getaway for some R&R with family or friends.

Oct 9 – 16

€ 70 per night

Guest favorite

Home in Campbellsport

4.99 out of 5 average rating, 136 reviews

Gleason's Chouse

You'll love staying in our unique home, in a quiet neighborhood. This is a recently remodeled 1867 church converted to a "Chouse". Featuring 2 bedrooms, Full Kitchen, 1 Bathroom, Balcony, Parking, and a Gazebo.. all beautifully complimented by a range of antiques and decorations. 8 Miles East of Hwy 41, a 45 min drive to Oshkosh or an hour to Milwaukee. Just down the from Lake Bernice & Eisenbahn Bike Trail. Also close enough to the Kettle Moraine Forest to hike and sightsee!

Feb 20 – 27

€ 128 per night

Guest favorite

Apartment in Sheboygan

4.92 out of 5 average rating, 394 reviews

Cozy Sheboygan Upper

We began caring for this home and property in 2018, and this 1870's home needed some love. We have been steadily remodeling since we moved in and it's starting to feel pretty great. We're excited to share it and the neighborhood with you. We are two blocks west of North Beach/Deland Park, 4 blocks to the river front boardwalk, home to many restaurants, cafe's, and shops. We are also four quick blocks to downtown which hosts many more restaurants, shops, museums and parks.

Oct 24 – 31

€ 96 per night

Guest favorite

Home in Glenbeulah

4.98 out of 5 average rating, 110 reviews

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 farm area, the recreation trail head is 3 miles east of us as well as the Wade House, we are near the Kettle Moraine State Forest and the Ice Age Trail and 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. Smoking is allowed outside of the home. No pets allowed.

Dec 18 – 25

€ 92 per night

Guest favorite

Apartment in Sheboygan

4.84 out of 5 average rating, 183 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

Sep 14 – 21

€ 78 per night

Guest favorite

Guesthouse in Sheboygan

4.83 out of 5 average rating, 367 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!

Jan 15 – 22

€ 139 per night

Guest favorite

Apartment in Waldo

4.98 out of 5 average rating, 258 reviews

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

Oct 16 – 23

€ 107 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Plymouth vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Plymouth's top sights

Walmart Supercenter7 locals recommend

Chester's Drive-In8 locals recommend

DeO's Pizzeria & Pub15 locals recommend

Antoinette's Casual Dining5 locals recommend

Piggly Wiggly15 locals recommend

Pacifico5 locals recommend

Other great vacation rentals in Plymouth

Superhost

Guest suite in Plymouth

4.83 out of 5 average rating, 100 reviews

De' Udder Place on the Water

Sep 23 – 30

€ 181 per night

Guest favorite

Home in Plymouth

4.94 out of 5 average rating, 80 reviews

Vintage Farmhouse on Blueberry Hill.

Feb 2 – 9

€ 182 per night

Guest favorite

Guest suite in Waldo

4.92 out of 5 average rating, 37 reviews

Above Garage Apartment w/ Private Beach

Nov 8 – 15

€ 112 per night

Guest favorite

Guest suite in Plymouth

4.97 out of 5 average rating, 75 reviews

Beautiful Luxury Condo Suite w/Large Deck

Jun 24 – Jul 1

€ 200 per night

Superhost

Guest suite in Sheboygan Falls

4.84 out of 5 average rating, 62 reviews

Hoppy Paddock - a private basement walk-out suite

Jun 27 – Jul 4

€ 92 per night

Guest favorite

Home in Waldo

4.97 out of 5 average rating, 61 reviews

Perfect Winter Getaway!

Feb 2 – 9

€ 124 per night

Guest favorite

Guest suite in Plymouth

5.0 out of 5 average rating, 22 reviews

Downtown Plymouth, WI Second Floor 2 Bed Apartment

Mar 18 – 25

€ 228 per night

Guest favorite

Home in Plymouth

5.0 out of 5 average rating, 25 reviews

Home-4 Bdrm-Private Pool+Hot Tub near Road America

Mar 5 – 12

€ 688 per night

Show all

Quick stats about vacation rentals in Plymouth

Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
2.1K reviews
Nightly prices starting at
€ 56 before taxes and fees

Frequently Asked Questions

What are the most popular amenities for House Rentals in Plymouth?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a kitchen, over 30 homes with free parking, over 30 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Plymouth?
Plymouth has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Plymouth have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Plymouth. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Plymouth have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Plymouth. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Plymouth?
Yes! Work meets play with ease at over 20 vacation rentals in Plymouth featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Plymouth?
Experience the best of Plymouth with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Plymouth have wifi?
Absolutely! We offer over 30 house rentals with wifi in Plymouth. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Plymouth have free parking?
Absolutely! We offer over 30 house rentals with free parking in Plymouth. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Plymouth

Top-rated vacation rentals in Plymouth

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Plymouth vacation rentals

Stay near Plymouth's top sights

Other great vacation rentals in Plymouth

Guest suite in Plymouth

Home in Plymouth

Guest suite in Waldo

Guest suite in Plymouth

Guest suite in Sheboygan Falls

Home in Waldo

Guest suite in Plymouth

Home in Plymouth

Quick stats about vacation rentals in Plymouth

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

What are the most popular amenities for House Rentals in Plymouth?

Are there family-friendly vacation rentals in Plymouth?

Do house rentals in Plymouth have air conditioning?

Do house rentals in Plymouth have a kitchen?

Are there vacation rentals with a dedicated workspace in Plymouth?

How much does it cost to stay in house rentals in Plymouth?

Do house rentals in Plymouth have wifi?

Do house rentals in Plymouth have free parking?

Destinations to explore