Holiday rentals near Old Plank Road Trailhead
We found 431 holiday rentals — enter your dates for availability
If you'd like to stay close to Old Plank Road Trailhead, take a look at holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a garden and pool. At the end of the day, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Old Plank Road Trailhead
Showing deals for:19 Sept - 26 Sept
Image gallery for Modern Lakeside House with Treehouse
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Modern Lakeside House with Treehouse
Sheboygan, WI
8% off
Price is NZ$12,692
NZ$12,692
NZ$1,813 per night
includes taxes & fees
Image gallery for Summit Woods Hideaway! Walking Distance To Road America. Elkhart Lake, WI 53020
1010 out of 10 rating
Exceptional
(18 reviews)
Summit Woods Hideaway! Walking Distance To Road America. Elkhart Lake, WI 53020
Plymouth, WI
8% off
Price is NZ$9,308
NZ$9,308
NZ$1,330 per night
includes taxes & fees
Image gallery for Private Ranch home hidden in the woods with lots of wildlife can sleep 11 guests
1010 out of 10 rating
Exceptional
(9 reviews)
Private Ranch home hidden in the woods with lots of wildlife can sleep 11 guests
Plymouth, WI
9% off
Price is NZ$9,644
NZ$9,644
NZ$1,378 per night
includes taxes & fees
Image gallery for Give Dad a memorable Father’s Day Weekend in Wisconsin!
1010 out of 10 rating
Exceptional
(80 reviews)
Give Dad a memorable Father’s Day Weekend in Wisconsin!
Sheboygan, WI
8% off
Price is NZ$26,009
NZ$26,009
NZ$3,716 per night
includes taxes & fees
Image gallery for Beautiful new year round Lake home on Long Lake in Kettle Moraine State forest
1010 out of 10 rating
Exceptional
(28 reviews)
Beautiful new year round Lake home on Long Lake in Kettle Moraine State forest
Cascade, WI
8% off
Price is NZ$5,270
NZ$5,270
NZ$753 per night
includes taxes & fees
Image gallery for BEST LAKE HOUSE, BEST BEACH HOUSE Lake Michigan, relaxing!
9.89.8 out of 10 rating
Exceptional
(70 reviews)
BEST LAKE HOUSE, BEST BEACH HOUSE Lake Michigan, relaxing!
Oostburg, wi
7% off
Price is NZ$5,425
NZ$5,425
NZ$775 per night
includes taxes & fees
Image gallery for Private, Peaceful Retreat near Road America
1010 out of 10 rating
Exceptional
(12 reviews)
Private, Peaceful Retreat near Road America
Plymouth, WI
8% off
Price is NZ$2,473
NZ$2,473
NZ$353 per night
includes taxes & fees
Image gallery for BEACHVIEW GETAWAY
9.89.8 out of 10 rating
Exceptional
(12 reviews)
BEACHVIEW GETAWAY
Sheboygan, WI
8% off
Price is NZ$5,141
NZ$5,141
NZ$734 per night
includes taxes & fees
Image gallery for Family Fun on Crystal Lake Island - minutes to Road America, hiking, PGA Golf
1010 out of 10 rating
Exceptional
(51 reviews)
Family Fun on Crystal Lake Island - minutes to Road America, hiking, PGA Golf
Plymouth, WI
8% off
Price is NZ$4,853
NZ$4,853
NZ$693 per night
includes taxes & fees
Image gallery for AAA 4 Diamond, Pristine Elkhart Lake, Award winning Spa, World Class Golf
1010 out of 10 rating
Exceptional
(25 reviews)
AAA 4 Diamond, Pristine Elkhart Lake, Award winning Spa, World Class Golf
Elkhart Lake, WI
8% off
Price is NZ$3,881
NZ$3,881
NZ$554 per night
includes taxes & fees
Image gallery for Country beauty on 5 acres
1010 out of 10 rating
Exceptional
(85 reviews)
Country beauty on 5 acres
Sheboygan Falls, WI
8% off
Price is NZ$2,850
NZ$2,850
NZ$407 per night
includes taxes & fees
Image gallery for Updated Victorian in the Heart of Sheboygan. Beach, Downtown, Golf, Road America
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Updated Victorian in the Heart of Sheboygan. Beach, Downtown, Golf, Road America
Sheboygan, WI
12% off
Price is NZ$3,940
NZ$3,940
NZ$563 per night
includes taxes & fees
Image gallery for BEACHSIDE GETAWAY IN SHEBOYGAN
1010 out of 10 rating
Exceptional
(21 reviews)
BEACHSIDE GETAWAY IN SHEBOYGAN
Sheboygan, WI
8% off
Price is NZ$3,413
NZ$3,413
NZ$488 per night
includes taxes & fees
Image gallery for Lime Ridge Vacation Rentals
1010 out of 10 rating
Exceptional
(22 reviews)
Lime Ridge Vacation Rentals
Elkhart Lake, WI
13% off
Price is NZ$3,563
NZ$3,563
NZ$509 per night
includes taxes & fees
Image gallery for Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
1010 out of 10 rating
Exceptional
(6 reviews)
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Sheboygan, WI
8% off
Price is NZ$6,523
NZ$6,523
NZ$932 per night
includes taxes & fees
Image gallery for Beautiful Remodeled Lake Michigan Beachfront Home Country Setting w/ 500mbps int
1010 out of 10 rating
Exceptional
(119 reviews)
Beautiful Remodeled Lake Michigan Beachfront Home Country Setting w/ 500mbps int
Oostburg, WI
8% off
Price is NZ$4,579
NZ$4,579
NZ$654 per night
includes taxes & fees
Image gallery for Country Homestead next to the City, with Perfect Location for Road America HPDE
9.69.6 out of 10 rating
Exceptional
(36 reviews)
Country Homestead next to the City, with Perfect Location for Road America HPDE
Plymouth, WI
17% off
Price is NZ$3,425
NZ$3,425
NZ$489 per night
includes taxes & fees
Image gallery for Good Vibes on the Third Coast-Pet Friendly! Cozy and Close by!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Good Vibes on the Third Coast-Pet Friendly! Cozy and Close by!
Sheboygan, WI
8% off
Price is NZ$2,684
NZ$2,684
NZ$383 per night
includes taxes & fees
Image gallery for The River Bed - Condo sleeps 4 on west side
1010 out of 10 rating
Exceptional
(72 reviews)
The River Bed - Condo sleeps 4 on west side
Sheboygan, WI
8% off
Price is NZ$2,071
NZ$2,071
NZ$296 per night
includes taxes & fees
Image gallery for Lakeside Condo - 2BR, Lake Michigan Views & Massage Chair
1010 out of 10 rating
Exceptional
(7 reviews)
Lakeside Condo - 2BR, Lake Michigan Views & Massage Chair
Sheboygan, WI
12% off
Price is NZ$3,666
NZ$3,666
NZ$524 per night
includes taxes & fees
Image gallery for Walk to Road America! Lake House on Private Peninsula
1010 out of 10 rating
Exceptional
(71 reviews)
Walk to Road America! Lake House on Private Peninsula
Plymouth, WI
8% off
Price is NZ$7,829
NZ$7,829
NZ$1,118 per night
includes taxes & fees
Image gallery for Sunset Views by Long Lake
1010 out of 10 rating
Exceptional
(9 reviews)
Sunset Views by Long Lake
Cascade, WI
8% off
Price is NZ$2,834
NZ$2,834
NZ$405 per night
includes taxes & fees
Image gallery for Wonderful 3+ Bedroom Home Completely Renovated
1010 out of 10 rating
Exceptional
(13 reviews)
Wonderful 3+ Bedroom Home Completely Renovated
Sheboygan, WI
19% off
Price is NZ$3,528
NZ$3,528
NZ$504 per night
includes taxes & fees
Image gallery for Beach front luxury spacious villa !
1010 out of 10 rating
Exceptional
(57 reviews)
Beach front luxury spacious villa !
Sheboygan, WI
8% off
Price is NZ$7,951
NZ$7,951
NZ$1,136 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Old Plank Road Trailhead
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
Sleeps 30 · 7 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Sunset Views by Long Lake
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!
Sleeps 9 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
Experience Wisconsin in an old farmhouse in the beautiful Kettle Moraine
Sleeps 30 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
Lillibridge Lake Home on Tittle Lake/Long Lake All Season Fun
Sleeps 7 · 2 bedrooms · 1+ bathroom
9.69.6 out of 10
Exceptionalexceptional
131 reviews(131 reviews)
Grand Rural Wisconsin Retreat: Full Indoor Gym
Sleeps 26 · 12 bedrooms · 12+ bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value