Holiday rentals near Old World Wisconsin
We found 569 holiday rentals — enter your dates for availability
Choose the perfect holiday rental that's near Old World Wisconsin. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as a pool and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Old World Wisconsin
Showing deals for:26 Sept - 3 Oct
Image gallery for LAKEFRONT HIDDEN GEM !
9.89.8 out of 10 rating
Exceptional
(31 reviews)
LAKEFRONT HIDDEN GEM !
Elkhorn, WI
12% off
Price is NZ$7,576
NZ$7,576
NZ$1,082 per night
includes taxes & fees
Image gallery for 3br Home-SwimSpa, Gym, near Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-Golfing
9.89.8 out of 10 rating
Exceptional
(16 reviews)
3br Home-SwimSpa, Gym, near Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-Golfing
Elkhorn, WI
20% off
Price is NZ$4,899
NZ$4,899
NZ$700 per night
includes taxes & fees
Image gallery for #2 Tamarack aka Como Escape · Como Escape 4 bed 3 bath by LAKE
1010 out of 10 rating
Exceptional
(19 reviews)
#2 Tamarack aka Como Escape · Como Escape 4 bed 3 bath by LAKE
Lake Geneva, WI
9% off
Price is NZ$5,312
NZ$5,312
NZ$759 per night
includes taxes & fees
Image gallery for "PHANTOM'S COVE": LAKE FRONT RETREAT ON UPPER PHANTOM LAKE
9.89.8 out of 10 rating
Exceptional
(52 reviews)
"PHANTOM'S COVE": LAKE FRONT RETREAT ON UPPER PHANTOM LAKE
Mukwonago, WI
8% off
Price is NZ$8,355
NZ$8,355
NZ$1,194 per night
includes taxes & fees
Image gallery for Charming, Pet-Friendly Lake Retreat
1010 out of 10 rating
Exceptional
(16 reviews)
Charming, Pet-Friendly Lake Retreat
Lake Geneva, Wisconsin
14% off
Price is NZ$4,045
NZ$4,045
NZ$578 per night
includes taxes & fees
Image gallery for Spectacular 77 acre estate, fishing ponds & close to Kettle Moraine trails
1010 out of 10 rating
Exceptional
(100 reviews)
Spectacular 77 acre estate, fishing ponds & close to Kettle Moraine trails
Eagle, WI
8% off
Price is NZ$4,566
NZ$4,566
NZ$652 per night
includes taxes & fees
Image gallery for W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants
9.69.6 out of 10 rating
Exceptional
(5 reviews)
W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants
Muskego, Wisconsin
13% off
Price is NZ$3,773
NZ$3,773
NZ$539 per night
includes taxes & fees
Image gallery for Stunning & Spacious Lookout Lodge |Half Acre Property |Floor-Ceiling Windows & Fireplace |Tree Views
1010 out of 10 rating
Exceptional
(5 reviews)
Stunning & Spacious Lookout Lodge |Half Acre Property |Floor-Ceiling Windows & Fireplace |Tree Views
Lake Geneva, WI
6% off
Price is NZ$14,207
NZ$14,207
NZ$2,030 per night
includes taxes & fees
Image gallery for Almost Heaven - Relaxing Getaway On Serene Rice Lake
1010 out of 10 rating
Exceptional
(63 reviews)
Almost Heaven - Relaxing Getaway On Serene Rice Lake
Whitewater, WI
7% off
Price is NZ$5,284
NZ$5,284
NZ$755 per night
includes taxes & fees
Image gallery for Luxury Property-Walk to lake and downtown Lake Geneva. Pet Friendly, Sleeps 8
1010 out of 10 rating
Exceptional
(8 reviews)
Luxury Property-Walk to lake and downtown Lake Geneva. Pet Friendly, Sleeps 8
Lake Geneva, WI
8% off
Price is NZ$6,807
NZ$6,807
NZ$972 per night
includes taxes & fees
Image gallery for Make Your Memories At Adorable Browns Lake/Cedar Park Cottage
1010 out of 10 rating
Exceptional
(32 reviews)
Make Your Memories At Adorable Browns Lake/Cedar Park Cottage
Burlington, WI
8% off
Price is NZ$3,245
NZ$3,245
NZ$464 per night
includes taxes & fees
Image gallery for The Tiny Bay House - Romantic Hideaway
1010 out of 10 rating
Exceptional
(18 reviews)
The Tiny Bay House - Romantic Hideaway
Williams Bay, WI
8% off
Price is NZ$2,360
NZ$2,360
NZ$337 per night
includes taxes & fees
Image gallery for Stunning Log Cabin Getaway Near Lake Beulah *Pool Table*Grill
9.89.8 out of 10 rating
Exceptional
(96 reviews)
Stunning Log Cabin Getaway Near Lake Beulah *Pool Table*Grill
Mukwonago, WI
8% off
Price is NZ$6,548
NZ$6,548
NZ$935 per night
includes taxes & fees
Image gallery for Paradise! Luxury 50-acre lakefront retreat. Swim, fish, kayak
1010 out of 10 rating
Exceptional
(25 reviews)
Paradise! Luxury 50-acre lakefront retreat. Swim, fish, kayak
Sullivan, WI
8% off
Price is NZ$20,551
NZ$20,551
NZ$2,936 per night
includes taxes & fees
Image gallery for Newly Renovated house steps from downtown and the lake
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Newly Renovated house steps from downtown and the lake
Lake Geneva, WI
8% off
Price is NZ$10,024
NZ$10,024
NZ$1,432 per night
includes taxes & fees
Image gallery for Forest Harmony House |Less than a Mile to Geneva Lake |Rec Room |Wet Bar | Quiet Street |Easy Access
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Forest Harmony House |Less than a Mile to Geneva Lake |Rec Room |Wet Bar | Quiet Street |Easy Access
Lake Geneva, WI
6% off
Price is NZ$4,157
NZ$4,157
NZ$594 per night
includes taxes & fees
Image gallery for Quick Trip Getaway |Fun Southwestern Vibe |Enclosed Porch |Walkable to Downtown Lake Geneva |Parking
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Quick Trip Getaway |Fun Southwestern Vibe |Enclosed Porch |Walkable to Downtown Lake Geneva |Parking
Lake Geneva, WI
6% off
Price is NZ$3,345
NZ$3,345
NZ$478 per night
includes taxes & fees
Image gallery for Lincoln Log Cabin · Elkhorn 3 Bedroom 2 Bathroom Log Cabin Sleeps 8
1010 out of 10 rating
Exceptional
(12 reviews)
Lincoln Log Cabin · Elkhorn 3 Bedroom 2 Bathroom Log Cabin Sleeps 8
Elkhorn, WI
13% off
Price is NZ$3,986
NZ$3,986
NZ$569 per night
includes taxes & fees
Image gallery for Secluded 3 bedroom Villa, Patio, BBQ + EV charger- Sleeps 9 max
1010 out of 10 rating
Exceptional
(10 reviews)
Secluded 3 bedroom Villa, Patio, BBQ + EV charger- Sleeps 9 max
Lake Geneva, WI
8% off
Price is NZ$5,874
NZ$5,874
NZ$839 per night
includes taxes & fees
Image gallery for Huge Family Home in Lake Geneva. Sleeps 10 Pet Friendly!
1010 out of 10 rating
Exceptional
(14 reviews)
Huge Family Home in Lake Geneva. Sleeps 10 Pet Friendly!
Lake Geneva, WI
8% off
Price is NZ$8,668
NZ$8,668
NZ$1,238 per night
includes taxes & fees
Image gallery for The Red Lodge - Unique Gem Near Lakes with Game Room and Hot Tub!
9.89.8 out of 10 rating
Exceptional
(16 reviews)
The Red Lodge - Unique Gem Near Lakes with Game Room and Hot Tub!
Elkhorn, WI
8% off
Price is NZ$5,675
NZ$5,675
NZ$811 per night
includes taxes & fees
Image gallery for Spacious Waterfront Home on Lake Delavan |Pier |Fire Pit |Deck |Retreat for Family, Friends or Work
1010 out of 10 rating
Exceptional
(77 reviews)
Spacious Waterfront Home on Lake Delavan |Pier |Fire Pit |Deck |Retreat for Family, Friends or Work
Delavan, WI
6% off
Price is NZ$9,291
NZ$9,291
NZ$1,327 per night
includes taxes & fees
Image gallery for ✨ Chic Retreat with Fire Pit- Near Downtown & Weddings Venues ✨
1010 out of 10 rating
Exceptional
(14 reviews)
✨ Chic Retreat with Fire Pit- Near Downtown & Weddings Venues ✨
Oconomowoc, WI
8% off
Price is NZ$5,477
NZ$5,477
NZ$782 per night
includes taxes & fees
Image gallery for Cozy, private, cabin on a quiet lake.
9.89.8 out of 10 rating
Exceptional
(63 reviews)
Cozy, private, cabin on a quiet lake.
Elkhorn, WI
8% off
Price is NZ$3,655
NZ$3,655
NZ$522 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Old World Wisconsin
Charming Country Cottage Guest House
Sleeps 2 · 1 bedroom · 1 bathroom
8.68.6 out of 10
Excellentexcellent
10 reviews(10 reviews)
Cozy 2 bedrm apart with full kitchen surrounded by woods 25 mins from Milwaukee
Sleeps 5 · 2 bedrooms
1010 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
Studio | Free Breakfast. Pool. Gym
Sleeps 4 · 1 bathroom
Free Breakfast. Pool. Gym. Close to Aurora Medical Center!
Sleeps 6 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Hidden Gem with Pool View!
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
35 reviews(35 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