Holiday rentals near Road America
We found 419 holiday rentals — enter your dates for availability
Choose the right holiday rental within easy reach of Road America. Holiday homes offer the best amenities for your family, friends or furry companion, such as parking and a pool. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Road America
Showing deals for:15 Aug - 22 Aug
Image gallery for Summit Woods Hideaway! Walking Distance To Road America. Elkhart Lake, WI 53020
1010 out of 10 rating
Exceptional
(17 reviews)
Summit Woods Hideaway! Walking Distance To Road America. Elkhart Lake, WI 53020
Plymouth, WI
8% off
Price is NZ$9,491
NZ$9,491
NZ$1,356 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$2,522
NZ$2,522
NZ$360 per night
includes taxes & fees
Image gallery for Large Farmhouse near RA & golf. Breakfast Included with lots of room for all!
1010 out of 10 rating
Exceptional
(5 reviews)
Large Farmhouse near RA & golf. Breakfast Included with lots of room for all!
Plymouth, WI
8% off
Price is NZ$9,707
NZ$9,707
NZ$1,387 per night
includes taxes & fees
Image gallery for Spacious Property, Hot Tub, Sleeps up to 9, EV Charger
1010 out of 10 rating
Exceptional
(29 reviews)
Spacious Property, Hot Tub, Sleeps up to 9, EV Charger
Cascade, WI
10% off
Price is NZ$5,260
NZ$5,260
NZ$751 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$5,532
NZ$5,532
NZ$790 per night
includes taxes & fees
Image gallery for Summer’s right around the corner! Book your group vacay while the going’s good.
1010 out of 10 rating
Exceptional
(80 reviews)
Summer’s right around the corner! Book your group vacay while the going’s good.
Sheboygan, WI
8% off
Price is NZ$27,224
NZ$27,224
NZ$3,889 per night
includes taxes & fees
Image gallery for Private Ranch home hidden in the woods with lots of wildlife to view.
1010 out of 10 rating
Exceptional
(9 reviews)
Private Ranch home hidden in the woods with lots of wildlife to view.
Plymouth, WI
9% off
Price is NZ$9,833
NZ$9,833
NZ$1,405 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$6,182
NZ$6,182
NZ$883 per night
includes taxes & fees
Image gallery for Ultimate Racing Fan Suite Near Road America – Relax Between Laps!
1010 out of 10 rating
Exceptional
(29 reviews)
Ultimate Racing Fan Suite Near Road America – Relax Between Laps!
Elkhart Lake, WI
16% off
Price is NZ$2,574
NZ$2,574
NZ$368 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
(35 reviews)
Country Homestead next to the City, with Perfect Location for Road America HPDE
Plymouth, WI
17% off
Price is NZ$3,493
NZ$3,493
NZ$499 per night
includes taxes & fees
Image gallery for Hidden Haven - Luxury Cottage w/ Hot Tub & Scenic Views
1010 out of 10 rating
Exceptional
(36 reviews)
Hidden Haven - Luxury Cottage w/ Hot Tub & Scenic Views
Cleveland, WI
13% off
Price is NZ$4,900
NZ$4,900
NZ$700 per night
includes taxes & fees
Image gallery for Private home on twenty wooded acres.
1010 out of 10 rating
Exceptional
(21 reviews)
Private home on twenty wooded acres.
Cascade, WI
8% off
Price is NZ$5,116
NZ$5,116
NZ$731 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$10,191
NZ$10,191
NZ$1,456 per night
includes taxes & fees
Image gallery for Remodeled lake house on Lake Michigan, near Kohler
1010 out of 10 rating
Exceptional
(11 reviews)
Remodeled lake house on Lake Michigan, near Kohler
Oostburg, WI
8% off
Price is NZ$8,007
NZ$8,007
NZ$1,144 per night
includes taxes & fees
Image gallery for Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony
1010 out of 10 rating
Exceptional
(9 reviews)
Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony
Sheboygan, WI
8% off
Price is NZ$10,066
NZ$10,066
NZ$1,438 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
12% off
Price is NZ$3,982
NZ$3,982
NZ$569 per night
includes taxes & fees
Image gallery for Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
1010 out of 10 rating
Exceptional
(17 reviews)
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Sheboygan, WI
8% off
Price is NZ$6,100
NZ$6,100
NZ$871 per night
includes taxes & fees
Image gallery for Quiet and Secluded CamperCabin at Camp Northern Lights
9.49.4 out of 10 rating
Exceptional
(38 reviews)
Quiet and Secluded CamperCabin at Camp Northern Lights
Campbellsport, WI
9% off
Price is NZ$2,234
NZ$2,234
NZ$319 per night
includes taxes & fees
Image gallery for Beautiful, newly built 3rd floor Townhouse in historic Elkhart Lake, WI.
1010 out of 10 rating
Exceptional
(28 reviews)
Beautiful, newly built 3rd floor Townhouse in historic Elkhart Lake, WI.
Plymouth, WI
8% off
Price is NZ$6,105
NZ$6,105
NZ$872 per night
includes taxes & fees
Image gallery for Classic brick charmer close to lake, river, and downtown!
1010 out of 10 rating
Exceptional
(13 reviews)
Classic brick charmer close to lake, river, and downtown!
Sheboygan, WI
8% off
Price is NZ$3,846
NZ$3,846
NZ$549 per night
includes taxes & fees
Image gallery for GGG Log Cabin Apartment on the Ice Age Trail
1010 out of 10 rating
Exceptional
(13 reviews)
GGG Log Cabin Apartment on the Ice Age Trail
Campbellsport, WI
8% off
Price is NZ$1,956
NZ$1,956
NZ$279 per night
includes taxes & fees
Image gallery for Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck
9.89.8 out of 10 rating
Exceptional
(24 reviews)
Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck
Sheboygan, WI
8% off
Price is NZ$2,979
NZ$2,979
NZ$426 per night
includes taxes & fees
Image gallery for LAKE HOUSE Relax'n in or on the water this is your place for memories to be made
9.49.4 out of 10 rating
Exceptional
(8 reviews)
LAKE HOUSE Relax'n in or on the water this is your place for memories to be made
Campbellsport, WI
17% off
Price is NZ$2,636
NZ$2,636
NZ$377 per night
includes taxes & fees
Image gallery for Beautiful Tent at Camp Northern Lights!
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Beautiful Tent at Camp Northern Lights!
Campbellsport, WI
8% off
Price is NZ$1,259
NZ$1,259
NZ$180 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Road America
cute and cozy-minutes from beaches,parks,trails,entertainment!
Sleeps 5 · 2 bedrooms · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
13 reviews(13 reviews)
*NEW* Sleeps 8 & Spacious!
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
22 reviews(22 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
32 reviews(32 reviews)
Plymouth Gem: Spacious Home with Bar, Game Room & Yard Near Road America
Sleeps 10 · 4 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Country beauty on 5 acres
Sleeps 6 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
84 reviews(84 reviews)
Racer’s Getaway - Rural, Upscale, Unique Home 8 minutes from Road America
Sleeps 8 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 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