Holiday rentals near Sky Trail
We found 945 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Sky Trail, take a look at holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include parking and a fireplace. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Sky Trail
Showing deals for:26 Sept - 3 Oct
Image gallery for New built w/free parking off Brady St. Fiserv Forum, Summer Fest and Lakefront!
1010 out of 10 rating
Exceptional
(9 reviews)
New built w/free parking off Brady St. Fiserv Forum, Summer Fest and Lakefront!
Milwaukee, WI
7% off
Price is NZ$5,732
NZ$5,732
NZ$819 per night
includes taxes & fees
Image gallery for Whole House in Bay View + Fenced-in Yard + Parking
1010 out of 10 rating
Exceptional
(8 reviews)
Whole House in Bay View + Fenced-in Yard + Parking
Milwaukee, WI
12% off
Price is NZ$3,609
NZ$3,609
NZ$516 per night
includes taxes & fees
Image gallery for Milwaukee Oasis: A Serene Retreat Near Lake Michigan
1010 out of 10 rating
Exceptional
(7 reviews)
Milwaukee Oasis: A Serene Retreat Near Lake Michigan
Milwaukee, WI
7% off
Price is NZ$1,874
NZ$1,874
NZ$268 per night
includes taxes & fees
Image gallery for Lake Drive Mansion ~ Downtown ~ Art Museum ~ Lakefront
1010 out of 10 rating
Exceptional
(10 reviews)
Lake Drive Mansion ~ Downtown ~ Art Museum ~ Lakefront
Milwaukee, WI
7% off
Price is NZ$14,081
NZ$14,081
NZ$2,012 per night
includes taxes & fees
Image gallery for Potter Upper · Bright 1.5BR in the Heart of Bay View - w/ Parking
1010 out of 10 rating
Exceptional
(6 reviews)
Potter Upper · Bright 1.5BR in the Heart of Bay View - w/ Parking
Milwaukee, WI
13% off
Price is NZ$2,974
NZ$2,974
NZ$425 per night
includes taxes & fees
Image gallery for Central Tosa home near downtown, state fair, froedtert
1010 out of 10 rating
Exceptional
(17 reviews)
Central Tosa home near downtown, state fair, froedtert
Milwaukee, WI
7% off
Price is NZ$2,655
NZ$2,655
NZ$379 per night
includes taxes & fees
Image gallery for You found a Gem! Emmersed in seclusion close to it all! 4 BRDM SLEEPS 12!
1010 out of 10 rating
Exceptional
(36 reviews)
You found a Gem! Emmersed in seclusion close to it all! 4 BRDM SLEEPS 12!
Brookfield, WI
7% off
Price is NZ$5,367
NZ$5,367
NZ$767 per night
includes taxes & fees
Image gallery for 4BD House, Your Central Suburban Oasis, City Lights, Quiet Nights
9.29.2 out of 10 rating
Wonderful
(14 reviews)
4BD House, Your Central Suburban Oasis, City Lights, Quiet Nights
Milwaukee, WI
11% off
Price is NZ$3,912
NZ$3,912
NZ$559 per night
includes taxes & fees
Image gallery for Beautiful English Mansion, 1/4 mile from Lake and close to Arts & Entertainment
1010 out of 10 rating
Exceptional
(87 reviews)
Beautiful English Mansion, 1/4 mile from Lake and close to Arts & Entertainment
Milwaukee, WI
7% off
Price is NZ$17,996
NZ$17,996
NZ$2,571 per night
includes taxes & fees
Image gallery for 3Kings, Renovated, FenceYard, Games, Ctr Loc
9.89.8 out of 10 rating
Exceptional
(9 reviews)
3Kings, Renovated, FenceYard, Games, Ctr Loc
Milwaukee, WI
22% off
Price is NZ$3,332
NZ$3,332
NZ$476 per night
includes taxes & fees
Image gallery for Milwaukee Bayview Getaway with Private Hot Tub
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Milwaukee Bayview Getaway with Private Hot Tub
Milwaukee, WI
7% off
Price is NZ$7,352
NZ$7,352
NZ$1,050 per night
includes taxes & fees
Image gallery for Brady St - Secret Garden - Fire Pit - Chic Victorian - Family Friendly
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Brady St - Secret Garden - Fire Pit - Chic Victorian - Family Friendly
Milwaukee, WI
7% off
Price is NZ$3,791
NZ$3,791
NZ$542 per night
includes taxes & fees
Image gallery for 3 bedroom Bayview house. Located in quiet residential area.
1010 out of 10 rating
Exceptional
(16 reviews)
3 bedroom Bayview house. Located in quiet residential area.
Milwaukee, WI
8% off
Price is NZ$2,712
NZ$2,712
NZ$387 per night
includes taxes & fees
Image gallery for Ultra Clean, Private, Comfy Home in Prime Location. Sleeps up to 8.
9.49.4 out of 10 rating
Exceptional
(12 reviews)
Ultra Clean, Private, Comfy Home in Prime Location. Sleeps up to 8.
Milwaukee, WI
7% off
Price is NZ$3,082
NZ$3,082
NZ$440 per night
includes taxes & fees
Image gallery for Modern and Convenient Waukesha 3BR home with 2 King Beds
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Modern and Convenient Waukesha 3BR home with 2 King Beds
Waukesha, WI
8% off
Price is NZ$2,959
NZ$2,959
NZ$423 per night
includes taxes & fees
Image gallery for Whitefish Bay 3Bedroom Entire House Sleeps 4
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Whitefish Bay 3Bedroom Entire House Sleeps 4
Milwaukee, WI
20% off
Price is NZ$3,340
NZ$3,340
NZ$477 per night
includes taxes & fees
Image gallery for Charming Pet-Friendly 3-BR Home, Backyard, Firepit, A/C, Centrally Located
1010 out of 10 rating
Exceptional
(10 reviews)
Charming Pet-Friendly 3-BR Home, Backyard, Firepit, A/C, Centrally Located
Milwaukee, WI
7% off
Price is NZ$3,679
NZ$3,679
NZ$526 per night
includes taxes & fees
Image gallery for Newly Remodeled Home!! Five minutes from Downtown Milwaukee
8.48.4 out of 10 rating
Very good
(40 reviews)
Newly Remodeled Home!! Five minutes from Downtown Milwaukee
Milwaukee, WI
7% off
Price is NZ$1,667
NZ$1,667
NZ$238 per night
includes taxes & fees
Image gallery for The Best Bungalow in Riverwest Parking onsite
9.69.6 out of 10 rating
Exceptional
(12 reviews)
The Best Bungalow in Riverwest Parking onsite
Milwaukee, WI
7% off
Price is NZ$3,030
NZ$3,030
NZ$433 per night
includes taxes & fees
Image gallery for NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
1010 out of 10 rating
Exceptional
(9 reviews)
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
Milwaukee, WI
7% off
Price is NZ$4,279
NZ$4,279
NZ$611 per night
includes taxes & fees
Image gallery for Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms
1010 out of 10 rating
Exceptional
(18 reviews)
Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms
Milwaukee, WI
24% off
Price is NZ$18,076
NZ$18,076
NZ$2,582 per night
includes taxes & fees
Image gallery for Best location in Milwaukee! Upper Duplex Unit - long term stays welcome
8.68.6 out of 10 rating
Excellent
(21 reviews)
Best location in Milwaukee! Upper Duplex Unit - long term stays welcome
Milwaukee, WI
7% off
Price is NZ$1,896
NZ$1,896
NZ$271 per night
includes taxes & fees
Image gallery for Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10
9.69.6 out of 10 rating
Exceptional
(236 reviews)
Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10
Milwaukee, WI
7% off
Price is NZ$4,579
NZ$4,579
NZ$654 per night
includes taxes & fees
Image gallery for Modern 3 BR Minutes to WI Statefair, MKE Zoo, Brewers, & Hospital
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Modern 3 BR Minutes to WI Statefair, MKE Zoo, Brewers, & Hospital
Milwaukee, WI
7% off
Price is NZ$3,264
NZ$3,264
NZ$466 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Sky Trail
Showing deals for: 23 Sept - 26 Sept
Family Retreat, private, large, great for multi-family, company retreat, wedding
Sleeps 36 · 11 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
The current price is NZ$8,542
NZ$8,542
for 3 nights, 1 home
NZ$2,847 per night
includes taxes & fees
17-acre Private Oasis estate with, an indoor pool, and private lake, sleeps 16
Sleeps 16 · 7 bedrooms · 6+ bathrooms
8.08.0 out of 10
Very goodvery good
1 review(1 review)
The current price is NZ$8,944
NZ$8,944
for 3 nights, 1 home
NZ$2,981 per night
includes taxes & fees
Lake Vacation/Hunters Lake in Dousman,WI, Milwaukee, Delafield, Oconomoc, Wales
Sleeps 5 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
81 reviews(81 reviews)
The current price is NZ$875
NZ$875
for 3 nights, 1 cottage
NZ$292 per night
includes taxes & fees
Waterfront Lake Cottage - Upper Nemahbin Lake
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
The current price is NZ$1,981
NZ$1,981
for 3 nights, 1 home
NZ$660 per night
includes taxes & fees
You found a Gem! Emmersed in seclusion close to it all! 4 BRDM SLEEPS 12!
Sleeps 12 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
The current price is NZ$2,705
NZ$2,705
for 3 nights, 1 home
NZ$902 per night
includes taxes & fees
Luxury Lakefront Home w Miles of Lake Views, private pier, lake toys & game room
Sleeps 11 · 6 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
The current price is NZ$5,473
NZ$5,473
for 3 nights, 1 home
NZ$1,824 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