Plymouth Holiday Rentals

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Holiday Rentals in Plymouth

Road America Adjacent Lake House with indoor pool

9.8 out of 10, Exceptional, (28)
"This was such a great location for our Road America weekend. The lake view and indoor pool was such a treat. "
Road America Adjacent Lake House with indoor pool

Summit Road Estate - Top Luxury

9.6 out of 10, Exceptional, (5)
"Our stay was phenomenal. The pool and the hot tub were such a plus. The house was super clean and had ample towels and blankets for us to use. The giant kitchen was equipped with all the necessities to make homemade meals. We did have an incident where there was a mouse in the master bedroom but was able to get it out of the house."
Summit Road Estate - Top Luxury

Stunning custom built country home with the ultimate game room!

10.0 out of 10, Exceptional, (26)
"This house was everything that it promised. The basement and backyard was used most - other than the bedrooms for just sleeping. The movie "theater" was spectacular. The backyard is set up for relaxing - just like vacations are supposed to do."
Stunning custom built country home with the ultimate game room!

Lakefront Plymouth Cottage w/ Private Hot Tub

9.8 out of 10, Exceptional, (8)
"Great location near the track. Beautiful lake and fall color views."
Lakefront Plymouth Cottage w/ Private Hot Tub

Grandstay Residential Suites Hotel - Sheboygan

2.5 star property
8.6 out of 10, Excellent, (866)
"Friendly staff. Great room. Ample breakfast. "
The price is AU$190
includes taxes & fees
26 Nov - 27 Nov
Grandstay Residential Suites Hotel - Sheboygan

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

9.8 out of 10, Exceptional, (229)
"This is a great place to stay! All the convenience of home and with an excellent view of the lake. Missing the sound of the waves already! There were binoculars to look out on the lake, games and puzzles, movies to watch. Close to shopping. Hour from Milwaukee or greenbay. It was a perfect place to stay and enjoy out visit with family close by. "
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Welcome to the "Lake Cottage" where lake Michigan waves are calling

10.0 out of 10, Exceptional, (121)
"This is my third time at the cabin and it never ceases to amaze me. Alan and Linda provide all of the perfect little personal touches and are easily available for questions if needed! I get my best sleep at this cabin and always go home the most relaxed I can be. Thank you again, Alan & Linda! "
Welcome to the "Lake Cottage" where lake Michigan waves are calling

Winter dates still available at Beachdaze!

10.0 out of 10, Exceptional, (123)
"We had such a wonderful time! The home was just perfect for the 4 of us- and with unexpected summer weather during a short fall weekend. The views and beach were incredible! It was so comfortable and clean, and had all the necessities and some extras. We look forward to coming back!"
Winter dates still available at Beachdaze!

Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

9.4 out of 10, Exceptional, (183)
"We rented the house for a family trip. The house is large and has plenty of room for all. The house is in a perfect spot to watch the morning sunrise. It was nice to sit outside and use the fire pit. You can't beat the view at this house. The owner answers questions and is nice. We could recommend staying at this house."
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

Lake Winnebago Waterfront Cottage W/Hot Tub

10.0 out of 10, Exceptional, (144)
"The property overall was so much more than what you read and see on the listing. I’ve stayed at countless properties on VRBO and other platforms. Jason was the host we all want. Communicative, helpful, professional, and friendly. Private lake access just steps away. A perfectly placed hot-tub. The inside of the home makes a perfect getaway for couples or families. I’m immeasurably grateful for Jason and everything he’s done to make this a destination that I look forward to visiting...
Lake Winnebago Waterfront Cottage W/Hot Tub

Beautifully restored lake house on the shores of Erler Lake.

9.6 out of 10, Exceptional, (200)
"Had a great weekend exploring the park, West Bend, and Lake Michigan. The Yahr House was just the right size for our family of ten. Could have used a few additional kitchen linens and washcloths to go with the towels. Thank you for a great place to stay!"
Beautifully restored lake house on the shores of Erler Lake.

REMODELED HOME ON LAKE MICHIGAN

10.0 out of 10, Exceptional, (146)
"Great place"
REMODELED HOME ON LAKE MICHIGAN

Fun Lake House On Long Lake Near Beaches 2 Bedroom Home by RedAwning

3.0 star property
Fun Lake House On Long Lake Near Beaches 2 Bedroom Home by RedAwning

Winter dates still available at Surfdaze!

10.0 out of 10, Exceptional, (94)
"We had a relaxing weekend on the lake. The bed was comfortable as were the couch and 2 chairs. The deck was a great place to sit and enjoy the sound and closeness of the lake. The windows offered full length views. It was just what we needed."
Winter dates still available at Surfdaze!

4 bed house on the shore of Lake Michigan

9.4 out of 10, Exceptional, (53)
"excellent lake access and views"
4 bed house on the shore of Lake Michigan

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

10.0 out of 10, Exceptional, (92)
"We absolutely loved our stay at the Sandalwood Cottage. We are a family of 5 (kids ages 5,4&2) and this was the perfect location! The house had everything we needed (kitchen supplies, towels, laundry, etc) it was exceptionally clean and close to all of the main Sheboygan attractions. We loved Bookworm Gardens and Above and Beyond Children’s Museum (both less than 15 minutes away). The yard was absolutely gorgeous and our kids had so much fun exploring the woods and playing on the swing set/tree...
The price is AU$247
includes taxes & fees
1 Dec - 2 Dec
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun

9.6 out of 10, Exceptional, (128)
"We love the fall colors in the fall - and Lilly pad is close to many hikes and scenic drives. The owners communicate in a timely fashion - and respond when we have questions. Beautiful deck if it's warm out - with a lake access and boats. Sulfur in the water - but you get used to it - there's a fresh water supply for drinking and coffee. "
Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun

The RandomCabin “On Random Lake”

9.8 out of 10, Exceptional, (45)
"This house and it’s location is perfect for quick getaway for the weekend. Dan was a great host with quick communication on check in and any other questions we had. Very close to a few establishments all with great friendly locals. We will definitely be back. "
The RandomCabin “On Random Lake”

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

10.0 out of 10, Exceptional, (11)
"Great spot for the fellas to crash during our golf getaway. Spacious and the beds were comfy. Easy walk to food and drinks. Thanks for being part of a memorable trip."
The price is AU$702
includes taxes & fees
3 Dec - 4 Dec
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

*NEW* Sleeps 8 & Spacious!

10.0 out of 10, Exceptional, (18)
"Not much to look at on the outside but inside was great! Location was great in town, clean and good beds and hot showers"
The price is AU$512
includes taxes & fees
26 Nov - 27 Nov
*NEW* Sleeps 8 & Spacious!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Plymouth you may be interested in

Baymont by Wyndham Plymouth

2.5 star property
9.0 out of 10, Wonderful, (507)
"Great stay"
The price is AU$204
includes taxes & fees
1 Dec - 2 Dec
Baymont by Wyndham Plymouth

Plymouth Inn

2.0 star property
6.8 out of 10, (455)
"Good price and still clean and comfy"
The price is AU$113
includes taxes & fees
2 Dec - 3 Dec
Plymouth Inn

AmericInn by Wyndham Plymouth

2.0 star property
8.6 out of 10, Excellent, (374)
"Stay was good- enjoyed having pool and hot tub."
The price is AU$162
includes taxes & fees
1 Dec - 2 Dec
AmericInn by Wyndham Plymouth
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Plymouth?

Yes, there are holiday rentals in Plymouth close to Sheboygan County Fairgrounds, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Plymouth has a good selection of restaurants and the bars. Make sure you have time to check out the shopping and golf courses during your trip.

What are some of the best holiday rentals that Plymouth has to offer?

Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room: This holiday home rental outside of Plymouth is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a private garden and a selection of games.

How many holiday rentals are there in Plymouth?

Expedia has 44 holiday rentals for your stay in Plymouth.

What’s there to see and do in Plymouth?

Explore the area and family-friendly sights such as Blue Harbor Resort & Conference Center Water Park, or get out into nature at a spot like Kettle Moraine State Forest. Road America and Antoinette are other places to visit while you're in town.

What’s a holiday rental in Plymouth like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Plymouth. Holiday rentals offer extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for small groups.