Holiday rentals near Whispering Pines Amphitheater
We found 373 holiday rentals — enter your dates for availability
If you are looking to stay near Whispering Pines Amphitheater, scroll through and discover private holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. No matter what you're looking for, you'll find a property to rent for everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Whispering Pines Amphitheater
Showing deals for:19 Sept - 26 Sept
Image gallery for Experience Gracious Living & Destination Kohler
1010 out of 10 rating
Exceptional
(6 reviews)
Experience Gracious Living & Destination Kohler
Sheboygan Falls, WI
5% off
Price is AU$14,929
AU$14,929
AU$2,133 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 AU$8,678
AU$8,678
AU$1,240 per night
includes taxes & fees
Image gallery for Experience Lake Michigan views from your cozy 3-bedroom retreat
1010 out of 10 rating
Exceptional
(24 reviews)
Experience Lake Michigan views from your cozy 3-bedroom retreat
Oostburg, WI
8% off
Price is AU$4,430
AU$4,430
AU$633 per night
includes taxes & fees
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 AU$11,364
AU$11,364
AU$1,623 per night
includes taxes & fees
Image gallery for Luxury private home on Lake Michigan with 5 acres near Whistling Straits Kohler
1010 out of 10 rating
Exceptional
(69 reviews)
Luxury private home on Lake Michigan with 5 acres near Whistling Straits Kohler
Cleveland, WI
8% off
Price is AU$6,492
AU$6,492
AU$927 per night
includes taxes & fees
Image gallery for Gather Your Group at the Bunkhouse!
1010 out of 10 rating
Exceptional
(45 reviews)
Gather Your Group at the Bunkhouse!
Port Washington, WI
8% off
Price is AU$10,885
AU$10,885
AU$1,555 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 AU$2,313
AU$2,313
AU$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 AU$8,996
AU$8,996
AU$1,285 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 AU$5,012
AU$5,012
AU$716 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
9% off
Price is AU$22,938
AU$22,938
AU$3,277 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 AU$3,578
AU$3,578
AU$511 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 AU$4,750
AU$4,750
AU$679 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 AU$2,631
AU$2,631
AU$376 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 AU$4,485
AU$4,485
AU$641 per night
includes taxes & fees
Image gallery for New Listing: Lake Michigan beach home: kayaks, games, PS5, foosball, volleyball
1010 out of 10 rating
Exceptional
(5 reviews)
New Listing: Lake Michigan beach home: kayaks, games, PS5, foosball, volleyball
Cleveland, WI
8% off
Price is AU$5,694
AU$5,694
AU$813 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 AU$3,633
AU$3,633
AU$519 per night
includes taxes & fees
Image gallery for Oostburg,WI Beach front, Lake Michigan
9.89.8 out of 10 rating
Exceptional
(61 reviews)
Oostburg,WI Beach front, Lake Michigan
Oostburg, WI
7% off
Price is AU$4,328
AU$4,328
AU$618 per night
includes taxes & fees
Image gallery for BEACHSIDE GETAWAY IN SHEBOYGAN
1010 out of 10 rating
Exceptional
(22 reviews)
BEACHSIDE GETAWAY IN SHEBOYGAN
Sheboygan, WI
8% off
Price is AU$3,151
AU$3,151
AU$450 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
9% off
Price is AU$7,114
AU$7,114
AU$1,016 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
7% off
Price is AU$2,510
AU$2,510
AU$359 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 AU$3,157
AU$3,157
AU$451 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 AU$4,230
AU$4,230
AU$604 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 AU$6,040
AU$6,040
AU$863 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
7% off
Price is AU$1,950
AU$1,950
AU$279 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Whispering Pines Amphitheater
Showing deals for: 13 Sept - 16 Sept
2 Mi to Road America: Pet-Friendly Duplex!
Sleeps 11 · 4 bedrooms · 2 bathrooms
The current price is AU$4,856
AU$4,856
for 3 nights, 1 home
AU$1,619 per night
includes taxes & fees
Updated Plymouth Home ~ 5 Mi to Road America!
Sleeps 6 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
The current price is AU$1,294
AU$1,294
for 3 nights, 1 home
AU$431 per night
includes taxes & fees
Good Vibes on the Third Coast-Pet Friendly! Cozy and Close by!
Sleeps 6 · 4 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
The current price is AU$1,305
AU$1,305
for 3 nights, 1 home
AU$435 per night
includes taxes & fees
Lake House - Great stay for Road America and Kohler golf
Sleeps 10 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
56 reviews(56 reviews)
The current price is AU$1,923
AU$1,923
for 3 nights, 1 cottage
AU$641 per night
includes taxes & fees
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