
Holiday rentals near Sky Trail
We found 876 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:14 Nov - 21 Nov
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
11% off
Price is NZ$3,046
NZ$3,046
NZ$435 per night
includes taxes & fees
Image gallery for Cottage near Mt. Mary College

1010 out of 10 rating
Exceptional
(16 reviews)
Cottage near Mt. Mary College
Milwaukee, WI
7% off
Price is NZ$2,576
NZ$2,576
NZ$368 per night
includes taxes & fees
Image gallery for Brew City Boho - Milwaukee Story Hill/Brewers

1010 out of 10 rating
Exceptional
(5 reviews)
Brew City Boho - Milwaukee Story Hill/Brewers
Milwaukee, WI
7% off
Price is NZ$4,644
NZ$4,644
NZ$663 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$1,871
NZ$1,871
NZ$267 per night
includes taxes & fees
Image gallery for Charming Riverfront Home l 4 BR l King Beds I Free Parking I Outdoor Haven

1010 out of 10 rating
Exceptional
(12 reviews)
Charming Riverfront Home l 4 BR l King Beds I Free Parking I Outdoor Haven
Milwaukee, WI
7% off
Price is NZ$4,117
NZ$4,117
NZ$588 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
12% off
Price is NZ$1,903
NZ$1,903
NZ$272 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
(15 reviews)
4BD House, Your Central Suburban Oasis, City Lights, Quiet Nights
Milwaukee, WI
11% off
Price is NZ$3,781
NZ$3,781
NZ$540 per night
includes taxes & fees
Image gallery for Charming remodeled 2-bedroom furnished home in safe, delightful Menomonee Falls

1010 out of 10 rating
Exceptional
(9 reviews)
Charming remodeled 2-bedroom furnished home in safe, delightful Menomonee Falls
Menomonee Falls, WI
8% off
Price is NZ$2,072
NZ$2,072
NZ$296 per night
includes taxes & fees
Image gallery for Milwaukee Home w/ Serene Patio & Backyard Garden!

9.89.8 out of 10 rating
Exceptional
(10 reviews)
Milwaukee Home w/ Serene Patio & Backyard Garden!
Milwaukee, WI
5% off
Price is NZ$2,235
NZ$2,235
NZ$319 per night
includes taxes & fees
Image gallery for You found a Gem! Emmersed in seclusion close to it all,4 BRDM SLEEPS 12!

9.89.8 out of 10 rating
Exceptional
(39 reviews)
You found a Gem! Emmersed in seclusion close to it all,4 BRDM SLEEPS 12!
Brookfield, WI
7% off
Price is NZ$4,343
NZ$4,343
NZ$620 per night
includes taxes & fees
Image gallery for Charming 2-bedroom house in enjoyable Milwaukee neighborhood with AC, WiFi

1010 out of 10 rating
Exceptional
(6 reviews)
Charming 2-bedroom house in enjoyable Milwaukee neighborhood with AC, WiFi
Milwaukee, WI
5% off
Price is NZ$2,210
NZ$2,210
NZ$316 per night
includes taxes & fees
Image gallery for JUST REMODELED Cozy, quiet,BrewersStadium Walk Distance. ClosetoDownTown,SteFair

8.08.0 out of 10 rating
Very good
(9 reviews)
JUST REMODELED Cozy, quiet,BrewersStadium Walk Distance. ClosetoDownTown,SteFair
Milwaukee, WI
7% off
Price is NZ$3,755
NZ$3,755
NZ$536 per night
includes taxes & fees
Image gallery for Central Tosa home near downtown, state fair, froedtert

1010 out of 10 rating
Exceptional
(21 reviews)
Central Tosa home near downtown, state fair, froedtert
Milwaukee, WI
7% off
Price is NZ$2,434
NZ$2,434
NZ$348 per night
includes taxes & fees
Image gallery for 3 bedroom Bayview house. Located in quiet residential area.

9.89.8 out of 10 rating
Exceptional
(20 reviews)
3 bedroom Bayview house. Located in quiet residential area.
Milwaukee, WI
8% off
Price is NZ$2,999
NZ$2,999
NZ$428 per night
includes taxes & fees
Image gallery for MKE River 3-LVL Townhouse 3BR+1.5BA with Parking for 2 Vehicles

9.69.6 out of 10 rating
Exceptional
(11 reviews)
MKE River 3-LVL Townhouse 3BR+1.5BA with Parking for 2 Vehicles
Milwaukee, WI
7% off
Price is NZ$3,007
NZ$3,007
NZ$430 per night
includes taxes & fees
Image gallery for Wonderful craftsman home in Wauwatosa

9.69.6 out of 10 rating
Exceptional
(44 reviews)
Wonderful craftsman home in Wauwatosa
Milwaukee, WI
8% off
Price is NZ$3,281
NZ$3,281
NZ$469 per night
includes taxes & fees
Image gallery for Whitefish Bay 3Bedroom Entire House Sleeps 4

9.69.6 out of 10 rating
Exceptional
(14 reviews)
Whitefish Bay 3Bedroom Entire House Sleeps 4
Milwaukee, WI
15% off
Price is NZ$3,559
NZ$3,559
NZ$508 per night
includes taxes & fees
Image gallery for Cozy Pet Friendly Home w/ Private Yard & King Bed - Near Wauwatosa

1010 out of 10 rating
Exceptional
(19 reviews)
Cozy Pet Friendly Home w/ Private Yard & King Bed - Near Wauwatosa
Milwaukee, WI
7% off
Price is NZ$2,499
NZ$2,499
NZ$357 per night
includes taxes & fees
Image gallery for Pink Door Place with fenced yard in a walkable area & 2 miles from Fiserv Forum

1010 out of 10 rating
Exceptional
(6 reviews)
Pink Door Place with fenced yard in a walkable area & 2 miles from Fiserv Forum
Milwaukee, WI
9% off
Price is NZ$2,310
NZ$2,310
NZ$330 per night
includes taxes & fees
Image gallery for Historic Greendale Original within short walking distance of the quaint village

9.89.8 out of 10 rating
Exceptional
(22 reviews)
Historic Greendale Original within short walking distance of the quaint village
Greendale, WI
14% off
Price is NZ$1,257
NZ$1,257
NZ$180 per night
includes taxes & fees
Image gallery for Ultra Clean, Private, Comfy Home in Prime Location. Sleeps up to 8.

9.69.6 out of 10 rating
Exceptional
(14 reviews)
Ultra Clean, Private, Comfy Home in Prime Location. Sleeps up to 8.
Milwaukee, WI
7% off
Price is NZ$3,078
NZ$3,078
NZ$440 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
(20 reviews)
Schlitz Castle: Huge 5BR/4BA Sleeps 12 w/ Double Kitchens & Living Rooms
Milwaukee, WI
25% off
Price is NZ$17,453
NZ$17,453
NZ$2,493 per night
includes taxes & fees
Image gallery for 4 Minutes Walk to Lake Michigan Atwater Park Beach, Backyard, Balconies. Pets

1010 out of 10 rating
Exceptional
(11 reviews)
4 Minutes Walk to Lake Michigan Atwater Park Beach, Backyard, Balconies. Pets
Milwaukee, WI
8% off
Price is NZ$3,959
NZ$3,959
NZ$566 per night
includes taxes & fees
Image gallery for 4 bd Victorian, close to downtown, great for groups and family gatherings

1010 out of 10 rating
Exceptional
(14 reviews)
4 bd Victorian, close to downtown, great for groups and family gatherings
Milwaukee, WI
8% off
Price is NZ$6,917
NZ$6,917
NZ$988 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Sky Trail
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
3 reviews(3 reviews)
Lake Vacation/Hunters Lake in Dousman,WI, Milwaukee, Delafield, Oconomoc, Wales
Sleeps 5 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
86 reviews(86 reviews)
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)
Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle
Sleeps 16 · 8 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Waterfront Lake Cottage - Upper Nemahbin Lake
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
Wooded Hills/Indoor Pool/Hot Tub/Arcade
Sleeps 12 · 5 bedrooms · 3+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
47 reviews(47 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