Holiday Homes in Plymouth

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Featured Holiday Homes in Plymouth

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!

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

Wander Back Inn to Elkhart Lake

10.0 out of 10, Exceptional, (29)
"Great property to house multiple people in a larger, comfortable setting. We were there supporting event at Road America. This location is short distance from Road America and also walking distance from the cute town of Elkhart Lake. "
Wander Back Inn to Elkhart Lake

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$246
includes taxes & fees
2 Dec - 3 Dec
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

10.0 out of 10, Exceptional, (173)
"Amazing host, house and location! The house was spotless and the hot tub was a hit! Very easy to follow instructions were provided. The host was very responsive, no issues and would recommend to anyone!"
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

Just completed new home focused on luxury, cleanliness, and convenient locatio

10.0 out of 10, Exceptional, (40)
"We were fortunate enough to stay while the leaves were changing for fall and everything in the area was just beautiful. Beds were quite comfortable, and I slept well. Easy check in/out, couldn't ask for a better place to stay."
Just completed new home focused on luxury, cleanliness, and convenient locatio

Beautiful 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!"
Beautiful Lake House on the Shores of Erler Lake.

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

NEW Three bedroom ranch style pet friendly home with a patio & theatre room!

10.0 out of 10, Exceptional, (24)
"We had a family event and the layout of the house and its location were just right. We loved the home theater and game rooms. The kitchen is well stocked and very functional. The location is quiet. It is outfitted for pets- right down to dog bowls. The hosts are super responsive!"
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!

Dog-Friendly Sheboygan Home - 1 Mi to Town!

9.8 out of 10, Exceptional, (6)
"Great space for quick stay. Very clean and close to everything!"
Dog-Friendly Sheboygan Home - 1 Mi to Town!

Gleason's Chouse

10.0 out of 10, Exceptional, (33)
"So interesting and comfy atmosphere. We loved all the attention to detail. Great amneties. Definitely going back!"
Gleason's Chouse

Riverfront Sheboygan Townhome w/ Grill!

10.0 out of 10, Exceptional, (10)
"Super cute, clean, fully stocked condo. Owners thought of everything!!! The beds were comfortable. Would highly recommend staying here"
Riverfront Sheboygan Townhome w/ Grill!

Beautiful 2 Bedroom Duplex

10.0 out of 10, Exceptional, (6)
"We stayed here while visiting our daughter at Marian university. The location was great and close to interstate access. Very clean unit and very pet friendly with many amenities for our small dogs. Very nicely decorated too and a beautiful yard. "
The price is AU$446
includes taxes & fees
3 Dec - 4 Dec
Beautiful 2 Bedroom Duplex

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

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

Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau

10.0 out of 10, Exceptional, (54)
"This property is exactly as described. It's well appointed for activities on the lake as well as amenities at the house. The kitchen had everything we needed to make breakfast for the family. This was a short <15 min drive to Brillion where we were attending a family wedding. Ron is a gracious and responsive host. We're already planning our return next Summer."
Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau

Insane luxury beachfront estate - complete with indoor pool, arcade and theater!

10.0 out of 10, Exceptional, (24)
"Our group of 12 have stayed over the weekend for the golf outing at the Whistling Straits Golf Course. Everyone loved this house and we had the best time ever. We will definitely come back in the near future. Thank you!!!"
Insane luxury beachfront estate - complete with indoor pool, arcade and theater!

Family and pet friendly house in beautiful Sandy Knoll County Park!

9.6 out of 10, Exceptional, (190)
"We had yet another perfect-weather weekend and enjoyed the firepit each day. Traffic bond has been added over the past several years, making it safer and more comfortable to sit around. Josh Hamm organized a Space Race Disc Golf round, hugely aporeciated by our family. The items that spell "Welcome" were orovided 5 years ago and are no longer. We ran out of TP - no extra rolls.No kitchen towels, no dishcloths or facecloths, few hand towels. No bedding for the futon; no extra bedding at all, such...
Family and pet friendly house in beautiful Sandy Knoll County Park!

4 Bedroom Beachfront Condo - Fantastic Lake View

10.0 out of 10, Exceptional, (60)
"Great place, view and everything about the place was very nice. "
4 Bedroom Beachfront Condo - Fantastic Lake View

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

9.8 out of 10, Exceptional, (8)
"Cozy and comfortable place. I really enjoyed the house. I would love to stay here again. "
The price is AU$254
includes taxes & fees
2 Dec - 3 Dec
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
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 property types 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!
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

Black Friday: Members save 30%+

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